3567:
substituents were attached; however, no such isomers were observed. In 1872, Kekulé suggested that benzene had two complementary structures and that these forms rapidly interconverted, so that if there were a double bond between any pair of carbon atoms at one instant, that double bond would become a single bond at the next instant (and vice versa). To provide a mechanism for the conversion process, Kekulé proposed that the valency of an atom is determined by the frequency with which it collided with its neighbors in a molecule. As the carbon atoms in the benzene ring collided with each other, each carbon atom would collide twice with one neighbor during a given interval and then twice with its other neighbor during the next interval. Thus, a double bond would exist with one neighbor during the first interval and with the other neighbor during the next interval. Therefore, between the carbon atoms of benzene there were no fixed (i.e., constant) and distinct single or double bonds; instead, the bonds between the carbon atoms were identical. See
1778:
1624:
3155:(OSHA) has set a permissible exposure limit of 1 part of benzene per million parts of air (1 ppm) in the workplace during an 8-hour workday, 40-hour workweek. The short term exposure limit for airborne benzene is 5 ppm for 15 minutes. These legal limits were based on studies demonstrating compelling evidence of health risk to workers exposed to benzene. The risk from exposure to 1 ppm for a working lifetime has been estimated as 5 excess leukemia deaths per 1,000 employees exposed. (This estimate assumes no threshold for benzene's carcinogenic effects.) OSHA has also established an action level of 0.5 ppm to encourage even lower exposures in the workplace.
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3166:(IDLH) concentration for benzene to 500 ppm. The current NIOSH definition for an IDLH condition, as given in the NIOSH Respirator Selection Logic, is one that poses a threat of exposure to airborne contaminants when that exposure is likely to cause death or immediate or delayed permanent adverse health effects or prevent escape from such an environment. The purpose of establishing an IDLH value is (1) to ensure that the worker can escape from a given contaminated environment in the event of failure of the respiratory protection equipment and (2) is considered a maximum level above which only a highly reliable
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3339:(FISH) with DNA probes to assess the effects of benzene along with the hematological tests as markers of hematotoxicity. Benzene metabolism involves enzymes coded for by polymorphic genes. Studies have shown that genotype at these loci may influence susceptibility to the toxic effects of benzene exposure. Individuals carrying variant of NAD(P)H:quinone oxidoreductase 1 (NQO1), microsomal epoxide hydrolase (EPHX) and deletion of the glutathione S-transferase T1 (GSTT1) showed a greater frequency of DNA single-stranded breaks.
82:
994:
1805:, only the parody had monkeys seizing each other in a circle, rather than snakes as in Kekulé's anecdote. Some historians have suggested that the parody was a lampoon of the snake anecdote, possibly already well known through oral transmission even if it had not yet appeared in print. Kekulé's 1890 speech in which this anecdote appeared has been translated into English. If the anecdote is the memory of a real event, circumstances mentioned in the story suggest that it must have happened early in 1862.
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3590:(The simplest average of all the collisions of a carbon atom comes from the sum of the collisions during the first two units of time, which then periodically repeat. … thus one sees that each carbon atom collides equally often with the two others against which it bumps, thus stands in exactly the same relation with its two neighbors. The usual structural formula for benzene expresses, of course, only the collisions that occur during
3215:. Most of these metabolites have some value as biomarkers of human exposure, since they accumulate in the urine in proportion to the extent and duration of exposure, and they may still be present for some days after exposure has ceased. The current ACGIH biological exposure limits for occupational exposure are 500 μg/g creatinine for muconic acid and 25 μg/g creatinine for phenylmercapturic acid in an end-of-shift urine specimen.
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2906:. Whereas alkenes can be hydrogenated near room temperatures, benzene and related compounds are more reluctant substrates, requiring temperatures >100 °C. This reaction is practiced on a large scale industrially. In the absence of the catalyst, benzene is impervious to hydrogen. Hydrogenation cannot be stopped to give cyclohexene or cyclohexadienes as these are superior substrates.
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1797:). This vision, he said, came to him after years of studying the nature of carbon-carbon bonds. This was seven years after he had solved the problem of how carbon atoms could bond to up to four other atoms at the same time. Curiously, a similar, humorous depiction of benzene had appeared in 1886 in a pamphlet entitled
1823:, a benzene derivative with the same core of six carbon atoms, Lonsdale obtained diffraction patterns. Through calculating more than thirty parameters, Lonsdale demonstrated that the benzene ring could not be anything but a flat hexagon, and provided accurate distances for all carbon-carbon bonds in the molecule.
1591:. Four years later, Mansfield began the first industrial-scale production of benzene, based on the coal-tar method. Gradually, the sense developed among chemists that a number of substances were chemically related to benzene, comprising a diverse chemical family. In 1855, Hofmann was the first to apply the word "
3588:"Das einfachste Mittel aller Stöße eines Kohlenstoffatoms ergiebt sich aus der Summe der Stöße der beiden ersten Zeiteinheiten, die sich dann periodisch wiederholen. … man sieht daher, daß jedes Kohlenstoffatom mit den beiden anderen, … daß diese Verschiedenheit nur eine scheinbare, aber keine wirkliche ist."
3369:
in the urine. After exposure to 63 to 405 mg/m of benzene for 1 to 5 hours, 51 to 87% was excreted in the urine as phenol over a period of 23 to 50 hours. In another human study, 30% of absorbed dermally applied benzene, which is primarily metabolized in the liver, was excreted as phenol in the urine.
3368:
Inhaled benzene is primarily expelled unchanged through exhalation. In a human study 16.4 to 41.6% of retained benzene was eliminated through the lungs within five to seven hours after a two- to three-hour exposure to 47 to 110 ppm and only 0.07 to 0.2% of the remaining benzene was excreted unchanged
3190:
Several tests can determine exposure to benzene. Benzene itself can be measured in breath, blood or urine, but such testing is usually limited to the first 24 hours post-exposure due to the relatively rapid removal of the chemical by exhalation or biotransformation. Most people in developed countries
4278:
In a footnote on page 43, Liebig, the journal's editor, suggested changing
Mitscherlich's original name for benzene (namely, "benzin") to "benzol", because the suffix "-in" suggested that it was an alkaloid (e.g., Chinin (quinine)), which benzene isn't, whereas the suffix "-ol" suggested that it was
3321:
Genetic polymorphisms in these enzymes may induce loss of function or gain of function. For example, mutations in CYP2E1 increase activity and result in increased generation of toxic metabolites. NQ01 mutations result in loss of function and may result in decreased detoxification. Myeloperoxidase
1792:
organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper. Here Kekulé spoke of the creation of the theory. He said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake biting its
3174:(RELs) for substances, including carcinogens. As benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the REL (10-hour) of 0.1 ppm. The NIOSH short-term exposure limit (STEL – 15 min) is 1 ppm.
3334:
seems to play an important role by protecting against benzene-induced DNA breaks and it is being identified as a new biomarker for exposure and effect. Benzene causes chromosomal aberrations in the peripheral blood leukocytes and bone marrow explaining the higher incidence of leukemia and multiple
4755:
In his 1890 paper, Armstrong represented benzene nuclei within polycyclic benzenoids by placing inside the benzene nuclei a letter "C", an abbreviation of the word "centric". Centric affinities (i.e., bonds) acted within a designated cycle of carbon atoms. From p. 102: " … benzene, according to
3148:), a nonenforceable health goal that would allow an adequate margin of safety for the prevention of adverse effects, is zero benzene concentration in drinking water. The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5 kg) or more of benzene be reported.
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unit of time, thus during one phase, and so one is led to the view doubly substituted derivatives must be different at positions 1,2 and 1,6 . If the idea just presented—or a similar one—can be regarded as correct, then follows therefrom that this difference is only an apparent , not a real
3566:
Critics pointed out a problem with Kekulé's original (1865) structure for benzene: Whenever benzene underwent substitution at the ortho position, two distinguishable isomers should have resulted, depending on whether a double bond or a single bond existed between the carbon atoms to which the
3364:
Outdoor air may contain low levels of benzene from automobile service stations, wood smoke, tobacco smoke, the transfer of gasoline, exhaust from motor vehicles, and industrial emissions. About 50% of the entire nationwide (United States) exposure to benzene results from smoking tobacco or from
1758:
published a paper in French (for he was then teaching in
Francophone Belgium) suggesting that the structure contained a ring of six carbon atoms with alternating single and double bonds. The next year he published a much longer paper in German on the same subject. Kekulé used evidence that had
4281:"Da diese Flüssigkeit aus der Benzoësäure gewonnen wird, und wahrscheinlich mit den Benzoylverbindungen im Zusammenhang steht, so gibt man ihr am besten den Namen Benzol, da der Name Benzoïn schon für die mit dem Bittermandelöl isomerische Verbindung von Liebig und Wöhler gewählt worden ist."
2979:, bone marrow abnormalities and cardiovascular disease. The specific hematologic malignancies that benzene is associated with include: acute myeloid leukemia (AML), aplastic anemia, myelodysplastic syndrome (MDS), acute lymphoblastic leukemia (ALL), and chronic myeloid leukemia (CML).
3322:
mutations result in loss of function and may result in decreased generation of toxic metabolites. GSH mutations or deletions result in loss of function and result in decreased detoxification. These genes may be targets for genetic screening for susceptibility to benzene toxicity.
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4283:(Since this liquid is obtained from benzoic acid and probably is related to benzoyl compounds, the best name for it is "benzol", since the name "benzoïn" has already been chosen, by Liebig and Wöhler, for the compound that's isomeric with the oil of bitter almonds .)
7148:
Eastmond, D.A.; Rupa, DS; Hasegawa, LS (2000). "Detection of hyperdiploidy and chromosome breakage in interphase human lymphocytes following exposure to the benzene metabolite hydroquinone using multicolor fluorescence in situ hybridization with DNA probes".
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smoke, automobile service stations, exhaust from motor vehicles, and industrial emissions; however, ingestion and dermal absorption of benzene can also occur through contact with contaminated water. Benzene is hepatically metabolized and excreted in the
1750:
in 1861 suggested possible structures that contained multiple double bonds or multiple rings, but in these years very little was known about aromatic chemistry, and so chemists were unable to adduce appropriate evidence to favor any particular formula.
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3290:. Hydroquinone, benzenetriol and catechol are converted to polyphenols. In the bone marrow, MPO converts these polyphenols to benzoquinones. These intermediates and metabolites induce genotoxicity by multiple mechanisms including inhibition of
2176:, and benzene is then separated from the other aromatics by distillation. The extraction step of aromatics from the reformate is designed to produce aromatics with lowest non-aromatic components. Recovery of the aromatics, commonly referred to as
6952:
Fustinoni S, Buratti M, Campo L, Colombi A, Consonni D, Pesatori AC, Bonzini M, Farmer P, Garte S, Valerio F, Merlo DF, Bertazzi PA (2005). "Urinary t,t-muconic acid, S-phenylmercapturic acid and benzene as biomarkers of low benzene exposure".
1835:
suggested the prefixes ortho-, meta-, para- to distinguish di-substituted benzene derivatives in 1867; however, he did not use the prefixes to distinguish the relative positions of the substituents on a benzene ring. It was the German chemist
1960:
have a similar structure, only the ring of delocalized electrons and the loss of one hydrogen per carbon distinguishes it from cyclohexane. The molecule is planar. The molecular orbital description involves the formation of three delocalized
12669:
2650:. In 2013, the biggest consumer country of benzene was China, followed by the USA. Benzene production is currently expanding in the Middle East and in Africa, whereas production capacities in Western Europe and North America are stagnating.
2621:
consumes around 10% of the world's benzene production; it is primarily used in the manufacture of nylon fibers, which are processed into textiles and engineering plastics. Smaller amounts of benzene are used to make some types of
2656:
is now often used as a substitute for benzene, for instance as a fuel additive. The solvent-properties of the two are similar, but toluene is less toxic and has a wider liquid range. Toluene is also processed into benzene.
2222:
catalyst at 500–650 °C and 20–60 atm pressure. Sometimes, higher temperatures are used instead of a catalyst (at the similar reaction condition). Under these conditions, toluene undergoes dealkylation to benzene and
4510:
Claus, Adolph K.L. (1867) "Theoretische
Betrachtungen und deren Anwendungen zur Systematik der organischen Chemie" (Theoretical considerations and their applications to the classification scheme of organic chemistry),
1879:, spot removers, and other products. Manufacture of some of these benzene-containing formulations ceased in about 1950, although Liquid Wrench continued to contain significant amounts of benzene until the late 1970s.
3005:
As benzene is ubiquitous in gasoline and hydrocarbon fuels that are in use everywhere, human exposure to benzene is a global health problem. Benzene targets the liver, kidney, lung, heart and brain and can cause
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exposure to tobacco smoke. After smoking 32 cigarettes per day, the smoker would take in about 1.8 milligrams (mg) of benzene. This amount is about 10 times the average daily intake of benzene by nonsmokers.
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If the raw material stream contains much non-aromatic components (paraffins or naphthenes), those are likely decomposed to lower hydrocarbons such as methane, which increases the consumption of hydrogen.
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Fracasso ME, Doria D, Bartolucci GB, Carrieri M, Lovreglio P, Ballini A, Soleo L, Tranfo G, Manno M (2010). "Low air levels of benzene: Correlation between biomarkers of exposure and genotoxic effects".
2986:(API) stated as early as 1948 that "it is generally considered that the only absolutely safe concentration for benzene is zero". There is no safe exposure level; even tiny amounts can cause harm. The
1840:
who, in 1869, first used the prefixes ortho-, meta-, para- to denote specific relative locations of the substituents on a di-substituted aromatic ring (viz, naphthalene). In 1870, the German chemist
2990:(DHHS) classifies benzene as a human carcinogen. Long-term exposure to excessive levels of benzene in the air causes leukemia, a potentially fatal cancer of the blood-forming organs. In particular,
3571:
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Williams, P.R.D.; Knutsen, J.S.; Atkinson, C.; Madl, A.K.; Paustenbach, D.J. (2007). "Airborne
Concentrations of Benzene Associated with the Historical Use of Some Formulations of Liquid Wrench".
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have measureable baseline levels of benzene and other aromatic petroleum hydrocarbons in their blood. In the body, benzene is enzymatically converted to a series of oxidation products including
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5538:
The identification of organic molecules in rocks on the red planet does not necessarily point to life there, past or present, but does indicate that some of the building blocks were present.
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The paradigm of toxicological assessment of benzene is shifting towards the domain of molecular toxicology as it allows understanding of fundamental biological mechanisms in a better way.
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3347:
One way of understanding the carcinogenic effects of benzene is by examining the products of biological oxidation. Pure benzene, for example, oxidizes in the body to produce an epoxide,
7075:
Dougherty, D; Garte, S; Barchowsky, A; Zmuda, J; Taioli, E (2008). "NQO1, MPO, CYP2E1, GSTT1 and STM1 polymorphisms and biological effects of benzene exposure—a literature review".
3298:(which maintains cellular structure and organization), generation of oxygen free radicals (unstable species) that may lead to point mutations, increasing oxidative stress, inducing
2717:
has led to stringent regulation of gasoline's benzene content, with limits typically around 1%. European petrol specifications now contain the same 1% limit on benzene content. The
3034:(ATSDR) (2007), benzene is both a synthetically made and naturally occurring chemical from processes that include: volcanic eruptions, wild fires, synthesis of chemicals such as
3108:
regulates levels of benzene in the workplace. The maximum allowable amount of benzene in workroom air during an 8-hour workday, 40-hour workweek is 1 ppm. As benzene can cause
3022:. Benzene causes cancer in animals including humans. Benzene has been shown to cause cancer in both sexes of multiple species of laboratory animals exposed via various routes.
2709:
replaced it as the most widely used antiknock additive. With the global phaseout of leaded gasoline, benzene has made a comeback as a gasoline additive in some nations. In the
2160:
hydrocarbons form rings and lose hydrogen to become aromatic hydrocarbons. The aromatic products of the reaction are then separated from the reaction mixture (or reformate) by
1767:
of benzene, and that there always appeared to be exactly three isomers of every disubstituted derivative—now understood to correspond to the ortho, meta, and para patterns of
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6874:. U.S. Department of Health and Human Services, Public Health Service, Centers for Disease Control, National Institute for Occupational Safety and Health. August 2007.
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5351:"On distingue facilement ces trois séries, dans lesquelles les dérivés bihydroxyliques ont leurs terms correspondants, par les préfixes ortho-, para- et mêta-."
1948:: the electrons for C=C bonding are distributed equally between each of the six carbon atoms. Benzene has 6 hydrogen atoms, fewer than the corresponding parent
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1771:—to argue in support of his proposed structure. Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 carbon-hydrogen ratio.
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5353:(One easily distinguishes these three series – in which the dihydroxy derivatives have their corresponding terms – by the prefixes ortho-, para- and meta-.)
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1521:), an aromatic resin known since ancient times in Southeast Asia, and later to European pharmacists and perfumers in the 16th century via trade routes. An
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Toxicological
Profile for benzene, between 1978 and 1981, catalytic reformates accounted for approximately 44–50% of the total U.S. benzene production.
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Moran D, Simmonett AC, Leach FE, Allen WD, Schleyer PV, Schaefer HF (2006). "Popular
Theoretical Methods Predict Benzene and Arenes To Be Nonplanar".
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1887:
Trace amounts of benzene are found in petroleum and coal. It is a byproduct of the incomplete combustion of many materials. For commercial use, until
1788:
The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both pure and applied chemistry that in 1890 the
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American
Conference of Governmental Industrial Hygienists (ACGIH) adopted Threshold Limit Values (TLVs) for benzene at 0.5 ppm TWA and 2.5 ppm STEL.
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at 0.005 mg/L (5 ppb), as promulgated via the U.S. National
Primary Drinking Water Regulations. This regulation is based on preventing benzene
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4311:(I give the name of "phène" (φαινω, I illuminate) to the fundamental radical of the preceding acids, because benzene is found in illuminating gas.)
4309:"Je donne le nom de phène au radical fondamental des acides précédens (φαινω, j'éclaire), puisque la benzine se trouve dans le gaz de l'éclairage."
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But many chemists had begun to work on aromatic substances, especially in
Germany, and relevant data was coming fast. In 1865, the German chemist
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1529:, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene.
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2446:
This is often called "on-purpose" methodology to produce benzene, compared to conventional BTX (benzene-toluene-xylene) extraction processes.
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2605:'s lists contained at least one benzene ring. More than half of the entire benzene production is processed into ethylbenzene, a precursor to
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related, benzene cannot be converted into pyridine. Replacement of a second CH bond with N gives, depending on the location of the second N,
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1973:. To reflect the delocalized nature of the bonding, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms.
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6326:"Traffic-related air pollution and the onset of myocardial infarction: disclosing benzene as a trigger? A small-area case-crossover study"
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Charles
Mansfield filed for (November 11, 1847) and received (May 1848) a patent (no. 11,960) for the fractional distillation of coal tar.
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Isaacson, Kristofer P.; Proctor, Caitlin R.; Wang, Q. Erica; Edwards, Ethan Y.; Noh, Yoorae; Shah, Amisha D.; Whelton, Andrew J. (2021).
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IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs
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On pages 443–450, Faraday discusses "bicarburet of hydrogen" (benzene). On pages 449–450, he shows that benzene's empirical formula is C
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Public Health Statement for Benzene, Agency for Toxic Substances and Disease Registry. (August 2007). Benzene: Patient information sheet
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first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name
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6898:"Blood concentrations of volatile organic compounds in a nonoccupationally exposed US population and in groups with suspected exposure"
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2517:. Pyrolysis gasoline can be blended with other hydrocarbons as a gasoline additive, or routed through an extraction process to recover
5285:
4206:, although he doesn't realize it because he (like most chemists at that time) used the wrong atomic mass for carbon (6 instead of 12).
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4558:"On the oxidation of phenyl alcohol, and a mechanical arrangement adapted to illustrate structure in the non-saturated hydrocarbons"
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in China with a population of almost nine million people, was cut off because of a major benzene exposure. Benzene leaked into the
3163:
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Kaiser, R. (1968). "Bicarburet of Hydrogen. Reappraisal of the Discovery of Benzene in 1825 with the Analytical Methods of 1968".
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are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is caused by electron
1867:. This process was later discontinued. Benzene was historically used as a significant component in many consumer products such as
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Garte, S; Taioli, E; Popov, T; Bolognesi, C; Farmer, P; Merlo, F (2000). "Genetic susceptibility to benzene toxicity in humans".
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7346:"Drinking water contamination from the thermal degradation of plastics: Implications for wildfire and structure fire response"
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2511:. Depending on the feedstock used to produce the olefins, steam cracking can produce a benzene-rich liquid by-product called
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Solubilities of Inorganic and Organic Compounds: A Compilation of Solubility Data from the Periodical Literature. Supplement
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The pathway for the metabolism of benzene is complex and begins in the liver. Several enzymes are involved. These include
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Armit, James Wilson; Robinson, Robert (1925). "Polynuclear heterocyclic aromatic types. Part II. Some anhydronium bases".
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4155:"On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat"
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of Auguste Kekulé (1872) "Ueber einige Condensationsprodukte des Aldehyds" (On some condensation products of aldehydes),
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Approximately 24,700,000 tons were produced in 1999. Highly instructive but of far less industrial significance is the
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2002:
Many important chemical compounds are derived from benzene by replacing one or more of its hydrogen atoms with another
810:
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when they are likely to be exposed to benzene at levels exceeding the recommended (8-hour) exposure limit of 0.1 ppm.
1595:" to designate this family relationship, after a characteristic property of many of its members. In 1997, benzene was
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Wilcox, David H.; Greenbaum, Frederick R. (1965). "Kekule's benzene ring theory: A subject for lighthearted banter".
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limits. The affected batches were removed from sale. Similar problems were reported by the FDA in the United States.
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1981:
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Thiele, Johannes (1899) "Zur Kenntnis der ungesättigten Verbindungen" (On our knowledge of unsaturated compounds),
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chemistry of low-valent metals. Important examples include the sandwich and half-sandwich complexes, respectively,
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caused hazardous conditions in multiple places, with the publication noting that the compound may eventually cause
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block with the code U+232C (⌬) to represent it with three double bonds, and U+23E3 (⏣) for a delocalized version.
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In some European languages, the word for petroleum or gasoline is an exact cognate of "benzene". For instance in
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81:
3712:"Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers"
2975:. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute
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Major commodity chemicals and polymers derived from benzene. Clicking on the image loads the appropriate article
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6292:
6264:
6063:"Kinetic modeling and thermodynamic analysis of toluene disproportionation reaction over ZSM-5 based catalysts"
5790:
Cooper, David L.; Gerratt, Joseph; Raimondi, Mario (1986). "The electronic structure of the benzene molecule".
2676:
1623:
1526:
940:
3170:
providing maximum worker protection is permitted. In September 1995, NIOSH issued a new policy for developing
2842:
Using electrophilic aromatic substitution, many functional groups are introduced onto the benzene framework.
14483:
14275:
11868:
10184:
4896:"VIII. Die aromatischen Verbindungen. Das Benzol." (VIII. The aromatic compounds. Benzene.), pp. 125–129.
4435:
The existence and mode of formation of insolinic acid prove that to the series of monobasic aromatic acids, C
3878:
2995:
7460:
7276:
5407:
5189:
Mémoires de la Classe des Sciences - Académie Royale des Sciences, des Lettres et des Beaux-arts de Belgique
1484:, such as the long-term results of accidental exposure, have been reported on by news organizations such as
14468:
14310:
12913:
7476:
4761:
2983:
2680:
2069:, carbon atoms in the benzene ring are replaced with other elements. The most important variations contain
1071:
358:
267:
7523:
6774:(ATSDR); Environmental Medicine & Environmental Health Education – CSEM. June 30, 2000. Archived from
5152:
Benfey O. T. (1958). "August Kekulé and the Birth of the Structural Theory of Organic Chemistry in 1858".
1969:. It is likely that this stability contributes to the peculiar molecular and chemical properties known as
998:
14523:
14518:
13506:
12637:
11748:
6841:
6811:
3087:; however, all of these have their limitations because benzene is rapidly metabolized in the human body.
1976:
Derivatives of benzene occur sufficiently often as a component of organic molecules, so much so that the
1580:
379:
229:
6032:
5614:
4673:
On p. 100, Kekulé suggests that the carbon atoms of benzene could form a "chaîne fermée" (closed chain).
3306:(which can affect gene expression). NQ01 and GSH shift metabolism away from toxicity. NQ01 metabolizes
993:
14458:
11758:
9757:
9347:
7887:
7685:
7312:
5379:
3624:
3171:
2757:
1768:
1584:
1266:
1253:
988:
7238:
4121:
Rocke, A. J. (1985). "Hypothesis and Experiment in the Early Development of Kekule's Benzene Theory".
1755:
1085:
14503:
14265:
14260:
13441:
6036:
4906:
3400:
3133:
2788:
2681:
2668:
2602:
1717:
1630:
1470:
1391:
279:
11773:
11768:
11763:
7295:
6775:
2670:
1903:
industry, necessitated the production of benzene from petroleum. Today, most benzene comes from the
14305:
12330:
12326:
11499:
9794:
7286:. Hazardous Substances Data Bank, U.S. National Library of Medicine. National Institutes of Health.
5331:
5050:
3818:
3399:
conducted a survey of 150 brands of soft drinks. It found that four contained benzene levels above
2999:
2998:(AML & ANLL) is caused by benzene. IARC rated benzene as "known to be carcinogenic to humans" (
2796:
2672:
2207:
to benzene. In this hydrogen-intensive process, toluene is mixed with hydrogen, then passed over a
2161:
1662:
1489:
1169:
396:
31:
17:
4895:
2671:
1694:
1687:
1616:
14508:
14385:
10267:
8279:
7543:
6304:
5515:
5111:
2666:
2484:(STDP) may be used. In this process, the xylene stream exiting the TDP unit is approximately 90%
1789:
1680:
1639:
744:
6745:
5691:
3274:), GSH, and myeloperoxidase (MPO). CYP2E1 is involved at multiple steps: converting benzene to
2480:) substantially exceeds demand for other xylene isomers, a refinement of the TDP process called
978:
14240:
13205:
13115:
12992:
12987:
10515:
10167:
9229:
8043:
7601:
6838:"Documentation for Immediately Dangerous to Life or Health Concentrations (IDLH): Introduction"
6163:
6134:
6003:
5974:
5367:
4527:(aromatic compounds), pp. 315–347, Claus presents Kekulé's hypothetical structure for benzene (
3426:
When plastic water pipes are subject to high heat, the water may be contaminated with benzene.
3378:
2991:
2899:
2664:
2613:. Some 20% of the benzene production is used to manufacture cumene, which is needed to produce
2066:
1904:
1764:
1747:
1743:
1703:
857:
6061:
Ali, M. A.; Haji, Shaker; Al-Khayyat, Mohammed; Abutaleb, Ahmed; Ahmed, Shakeel (2022-12-01).
5004:
4962:
4715:
4601:
4357:
4322:
3772:
1965:
spanning all six carbon atoms, while the valence bond description involves a superposition of
14493:
14295:
14270:
13908:
13526:
13073:
12860:
12538:
10274:
10162:
9290:
9224:
7880:
7678:
6619:"The toxicity of benzene and its metabolism and molecular pathology in human risk assessment"
6502:
6465:
6403:
4934:
4557:
4297:
4244:
3621:
Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
3490:
3392:
3291:
2145:
1993:
1966:
1783:
Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds
1454:
1021:
971:
677:
7508:
Dept. of Health and Human Services: TR-289: Toxicology and Carcinogenesis Studies of Benzene
5042:
3247:
with two double bonds, breaking the aromaticity. Next, the diol is newly reduced by NADH to
2705:. As a consequence, gasoline often contained several percent benzene before the 1950s, when
1059:
14463:
14356:
14340:
13965:
13336:
13307:
13188:
13012:
12642:
11268:
11143:
10243:
9688:
8808:
8607:
7613:
7607:
7248:, Agency for Toxic Substances and Disease Registry, Department of Health and Human Services
7229:, Agency for Toxic Substances and Disease Registry, Department of Health and Human Services
6958:
6437:, Agency for Toxic Substances and Disease Registry, Department of Health and Human Services
6337:
5940:
5895:
5846:
5799:
5705:
5631:
5561:
5267:
5224:
5161:
5084:
4484:
4292:
Laurent, (1836) "Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique,"
4035:
3725:
3439:
2927:
2843:
2558:
1945:
1899:
industry. However, in the 1950s, increased demand for benzene, especially from the growing
1538:
1442:
983:
589:
367:
189:
117:
100:
11732:
6819:
6197:
5253:
4154:
3958:
3888:, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-29)
2721:
introduced new regulations in 2011 that lowered the benzene content in gasoline to 0.62%.
2488:-xylene. In some systems, even the benzene-to-xylenes ratio is modified to favor xylenes.
51:
8:
14533:
14300:
14280:
14093:
13783:
13271:
13135:
13110:
13078:
12997:
12768:
12651:
11778:
11704:
10793:
10635:
10343:
9549:
9136:
7803:
7798:
7483:
6867:
6684:
5043:
4716:"An explanation of the laws which govern substitution in the case of benzenoid compounds"
4513:
Berichte über die Verhandlungen der Naturforschenden Gesellschaft zu Freiburg im Breisgau
2972:
2923:
2554:
2110:
1330:
1093:
578:
249:
155:
7450:
6962:
6341:
6218:
Stranks, D. R.; M. L. Heffernan; K. C. Lee Dow; P. T. McTigue; G. R. A. Withers (1970).
5944:
5899:
5850:
5803:
5709:
5635:
5565:
5271:
5228:
5165:
5088:
4488:
3729:
3681:
Arnold, D.; Plank, C.; Erickson, E.; Pike, F. (1958). "Solubility of Benzene in Water".
3351:, which is not excreted readily and can interact with DNA to produce harmful mutations.
3067:. Measurement of air and water levels of benzene is accomplished through collection via
2352:
This irreversible reaction is accompanied by an equilibrium side reaction that produces
2180:(benzene, toluene and xylene isomers), involves such extraction and distillation steps.
209:
165:
14448:
14398:
14320:
14290:
14235:
14112:
14088:
13587:
13521:
13386:
13346:
13197:
13160:
13120:
13099:
13042:
13017:
12745:
12408:
12306:
11963:
11596:
10968:
10570:
9323:
9280:
8138:
8128:
7815:
7788:
7783:
7595:
7536:
7209:
7052:
7027:
6643:
6618:
6548:
6523:
6475:
6448:
6412:
6387:
6360:
6325:
6108:
5956:
5913:
5864:
5815:
5737:
5729:
5657:
5595:
5520:
5460:
4426:
4178:
3463:
3068:
2823:
2819:
2736:
The most common reactions of benzene involve substitution of a proton by other groups.
2713:, concern over its negative health effects and the possibility of benzene entering the
2546:
2513:
2508:
2455:
1759:
accumulated in the intervening years—namely, that there always appeared to be only one
1485:
804:
7471:
5343:
Bulletins de l'Académie royale des sciences, des lettres et des beaux-arts de Belgique
5308:"Meet Kathleen Lonsdale, the physicist and prison reformer who cracked benzene's code"
4649:
400:
271:
14498:
14345:
13928:
13828:
13798:
13716:
13456:
13341:
13297:
13245:
13052:
13047:
12979:
12888:
12659:
12602:
12543:
12311:
11883:
10978:
10755:
10750:
10298:
10233:
10203:
9961:
9583:
9214:
9186:
9029:
8789:
8784:
8622:
8143:
7861:
7856:
7645:
7590:
7585:
7257:
7201:
7166:
7162:
7130:
7092:
7057:
7009:
6974:
6920:
6648:
6580:
6553:
6480:
6417:
6365:
6288:
6260:
6227:
6223:
6084:
5772:
5721:
5649:
5622:
5587:
5552:
5494:
5452:
5206:
5054:
5010:
4963:"Untersuchungen über aromatische Verbindungen (Investigations of aromatic compounds)"
4840:
4123:
4098:
3898:
3778:
3753:
3748:
3711:
3661:
3636:
3260:
3223:
Even if it is not a common substrate for metabolism, benzene can be oxidized by both
3072:
3015:
2200:
2169:
1933:
1820:
1816:
1812:
1727:
1466:
1387:
1291:
667:
38:
12931:
7213:
6897:
5917:
5819:
5741:
5661:
5599:
5464:
5187:
Gillis Jean (1966). "Auguste Kekulé et son oeuvre, réalisée à Gand de 1858 à 1867".
4430:
3924:
2866:), which is a strong electrophile produced by combining sulfuric and nitric acids.
1907:, with only a small fraction being produced from coal. Benzene has been detected on
1832:
1465:, of which billions of kilograms are produced annually. Although benzene is a major
14443:
14422:
14410:
14330:
14230:
14135:
14083:
13516:
13391:
13356:
13277:
13265:
13225:
13130:
13063:
12564:
12230:
11717:
11494:
11464:
11396:
11303:
10973:
10853:
10745:
10457:
10447:
9938:
9432:
9370:
9178:
7840:
7640:
7357:
7193:
7158:
7122:
7084:
7047:
7039:
6966:
6912:
6845:
6666:
Occupational Safety and Health Standards, Toxic and Hazardous Substances, 1910.1028
6638:
6630:
6543:
6535:
6470:
6460:
6407:
6399:
6355:
6345:
6252:
6074:
5960:
5948:
5903:
5868:
5854:
5807:
5764:
5713:
5639:
5577:
5569:
5486:
5444:
5275:
5254:"An X-Ray Analysis of the Structure of Hexachlorobenzene, Using the Fourier Method"
5232:
5169:
5123:
5092:
4974:
4871:
4830:
4802:
4727:
4697:
4613:
4571:
4492:
4418:
4369:
4334:
4258:
4225:
4168:
4132:
3743:
3733:
3692:
3628:
3099:
2725:
2003:
1710:
1653:
1411:
1384:
757:
547:
463:
6256:
4459:
Cernicharo, José; et al. (1997), "Infrared Space Observatory's Discovery of C
2910:, a non catalytic process, however selectively hydrogenates benzene to the diene.
1671:
1063:
14018:
13993:
13531:
13471:
13255:
13155:
13140:
13125:
13032:
13022:
12856:
12721:
12705:
12693:
12647:
12598:
12413:
12388:
12383:
12197:
11930:
11783:
10585:
10580:
10442:
10375:
10157:
9916:
9911:
9894:
9877:
9678:
9427:
9328:
9285:
9194:
9068:
8033:
8023:
7775:
7635:
7283:
7264:
7245:
7126:
7088:
6916:
6691:
6672:
6605:
6509:
6350:
6311:
6247:
Welch, Vincent A.; Fallon, Kevin J.; Gelbke, Heinz-Peter (2005). "Ethylbenzene".
6196:. U.S. Environmental Protection Agency. 2006-03-29. p. 15853. Archived from
6079:
6062:
5931:
Harcourt, Richard D. (1987). "The electronic structure of the benzene molecule".
5338:
4913:
4902:
4304:
4249:
4150:
3965:
3847:
3575:
3547:
3477:
3267:
3039:
2907:
2851:
2706:
2702:
2566:
2542:
2518:
2177:
1936:
shows that all six carbon-carbon bonds in benzene are of the same length, at 140
1868:
1853:
1809:
1561:
1549:
1530:
1518:
1182:
818:
7498:
7226:
6598:
6217:
5332:"Faits pour servir à la détermination du lieu chimique dans la série aromatique"
4001:
2156:
at 500–525 °C and pressures ranging from 8–50 atm. Under these conditions,
1564:
named the substance "phène"; this word has become the root of the English word "
331:
14255:
14220:
14003:
13893:
13858:
13843:
13778:
13773:
13672:
13572:
13491:
13466:
13431:
13376:
13351:
13220:
13068:
12868:
12697:
12606:
12473:
12468:
11892:
10780:
10685:
10560:
10525:
10520:
10406:
10371:
10228:
10223:
10099:
10094:
10089:
9882:
9849:
9633:
9615:
9605:
9259:
9254:
9219:
9170:
9076:
8048:
8038:
7810:
7770:
7573:
6435:
American Petroleum Institute, API Toxicological Review, Benzene, September 1948
5615:"Organic matter preserved in 3-billion-year-old mudstones at Gale crater, Mars"
3717:
Proceedings of the National Academy of Sciences of the United States of America
3543:
3396:
3141:
3137:
2959:
A bottle of benzene. The warnings show benzene is a toxic and flammable liquid.
2728:
the word 'benzina' can be used for gasoline, though now it is relatively rare.
2496:
2118:
1872:
1857:
1469:, it finds limited use in consumer items because of its toxicity. Benzene is a
1339:
716:
704:
690:
7493:
7197:
6995:. American Conference of Governmental Industrial Hygienists, Cincinnati, Ohio.
6970:
6539:
5448:
5127:
4575:
4136:
4063:"Gas Piped into Homes Contains Benzene and Other Risky Chemicals, Study Finds"
3984:
1224:
1206:
14437:
14285:
14140:
14023:
13998:
13979:
13923:
13803:
13761:
13756:
13496:
13486:
13446:
13321:
13215:
13170:
13145:
13027:
13007:
12864:
12827:
12701:
12627:
12622:
12612:
12548:
12488:
12418:
12263:
12220:
11426:
11391:
11366:
11178:
11038:
11018:
11013:
11003:
10998:
10898:
10788:
10730:
10725:
10710:
10690:
10680:
10660:
10650:
10640:
10605:
10575:
10565:
10510:
10434:
10381:
10366:
10248:
10196:
10127:
10013:
10003:
9998:
9988:
9983:
9933:
9928:
9844:
9839:
9829:
9683:
9638:
9600:
9588:
9559:
9437:
8936:
8743:
8733:
8229:
7512:
6088:
5725:
5490:
5414:
5386:
4978:
4875:
4701:
4617:
4373:
4338:
4262:
3954:
3684:
Industrial & Engineering Chemistry Chemical & Engineering Data Series
3535:
3515:
3457:
3416:
3388:
3348:
3335:
myeloma caused by chronic exposure. These aberrations can be monitored using
3212:
2887:
2875:
2808:
2710:
2698:
2586:
2581:
Benzene is used mainly as an intermediate to make other chemicals, above all
2570:
2443:
and heavier aromatics are used in place of toluene, with similar efficiency.
1997:
1876:
1569:
1553:
1434:
838:
596:
536:
526:
260:
136:
Cyclohexa-1,3,5-triene; 1,3,5-Cyclohexatriene (theoretical resonance isomers)
7043:
5644:
5573:
5341:(Facts to be used in determining chemical location in the aromatic series),
4013:
2529:
Although of no commercial significance, many other routes to benzene exist.
2058:. The limit of the fusion process is the hydrogen-free allotrope of carbon,
1837:
1039:
14361:
14215:
14068:
14008:
13988:
13960:
13888:
13768:
13751:
13706:
13657:
13562:
13282:
13235:
13083:
12736:
12478:
12428:
12398:
12343:
12301:
12296:
12291:
12281:
12276:
12205:
11863:
11828:
11823:
11793:
11742:
11669:
11361:
11351:
11123:
11118:
11108:
11103:
11033:
10858:
10848:
10740:
10700:
10665:
10645:
10630:
10615:
10550:
10545:
10530:
10500:
10495:
10480:
10426:
10416:
10179:
10066:
10061:
10038:
9789:
9628:
9554:
9491:
9486:
9464:
9420:
9405:
9395:
9042:
9006:
8902:
8675:
8665:
8574:
8564:
8554:
8095:
8085:
8075:
7737:
7727:
7717:
7630:
7317:
7205:
7134:
7113:
7096:
6978:
6584:
6557:
6484:
6421:
6369:
5776:
5717:
5653:
5591:
5456:
5280:
5237:
5210:
4939:(in German). Vienna, Austria-Hungary: Carl Gerold's Sohn. pp. 30, 65.
4844:
4422:
4229:
4173:
4084:
3539:
3531:
3511:
3435:
3384:
3307:
3295:
3283:
3256:
3208:
3192:
2894:
and derivatives. This reaction is achieved by the use of high pressures of
2867:
2792:
2598:
2582:
2538:
2191:
commercialized a method from LPG (mainly propane and butane) to aromatics.
2142:
2051:
1888:
1841:
1573:
1545:
1542:
1481:
1458:
784:
7170:
7061:
6924:
6652:
6524:"Benzene-induced cancers: abridged history and occupational health impact"
3757:
3738:
3632:
3314:(counteracting the effect of MPO). GSH is involved with the formation of
1925:
1145:
1035:
14335:
14245:
14210:
14177:
14103:
14078:
13918:
13823:
13793:
13677:
13592:
13582:
13312:
13240:
12818:
12813:
12783:
12763:
12518:
12498:
12448:
12271:
12253:
12248:
12238:
12215:
12210:
12177:
12099:
11940:
11907:
11897:
11753:
11737:
11641:
11524:
11441:
11421:
11411:
11381:
11346:
11298:
11288:
11248:
11243:
11218:
11203:
11163:
11153:
11088:
11058:
11008:
10953:
10928:
10908:
10903:
10868:
10765:
10720:
10675:
10655:
10620:
10595:
10490:
10467:
10391:
10361:
10238:
10191:
10152:
10033:
9921:
9906:
9901:
9889:
9454:
9449:
9415:
9410:
9400:
9378:
9090:
9047:
9020:
8954:
8917:
8836:
8690:
8670:
8657:
8589:
8584:
8579:
8569:
8559:
8546:
8377:
8110:
8105:
8100:
8090:
8080:
8067:
7903:
7752:
7747:
7742:
7732:
7722:
7701:
7488:
6634:
6183:
Kolmetz, Gentry, Guidelines for BTX Revamps, AIChE 2007 Spring Conference
5408:"Untersuchungen über die Constitution der zweifach-substituirten Benzole"
4806:
4731:
3527:
3523:
3507:
3503:
3502:
Six-membered aromatic rings with one carbon replaced by another element:
3391:(Vitamin C) may interact to produce benzene. In March 2006, the official
3331:
3311:
3303:
3232:
3084:
3011:
2891:
2878:
in the presence of a Lewis acid catalyst such as aluminium tri-chloride.
2749:
2741:
2714:
2618:
2610:
2594:
2534:
2134:
2043:
1970:
1957:
1941:
1920:
1892:
1646:
1592:
1449:
liquid with a sweet smell, and is partially responsible for the aroma of
1423:
1158:
604:
12883:
3696:
2042:. Further loss of hydrogen gives "fused" aromatic hydrocarbons, such as
1488:. For instance, a 2022 article stated that benzene contamination in the
1131:
14250:
14192:
14155:
14130:
14028:
13838:
13701:
12851:
12803:
12798:
12716:
12711:
12617:
12588:
12584:
12493:
12458:
12403:
12393:
12353:
12286:
12114:
12079:
12044:
12039:
11993:
11983:
11912:
11873:
11833:
11818:
11798:
11788:
11727:
11722:
11712:
11679:
11661:
11557:
11504:
11469:
11416:
11406:
11376:
11371:
11308:
11283:
11238:
11213:
11193:
11173:
11168:
11158:
11138:
11093:
11083:
11068:
11028:
11023:
10993:
10948:
10943:
10923:
10913:
10893:
10888:
10878:
10838:
10833:
10828:
10823:
10818:
10808:
10803:
10798:
10770:
10625:
10540:
10535:
10421:
10411:
10386:
10147:
10138:
10018:
9973:
9869:
9834:
9824:
9764:
9700:
9623:
9571:
9149:
9037:
8841:
8728:
8718:
8647:
8382:
8204:
8199:
8174:
8028:
8018:
7362:
7345:
5733:
5582:
4813:
A history of the determination of benzene's structure is recounted in:
3252:
3080:
3076:
2964:
2812:
2768:
2212:
2094:
2090:
2047:
1477:
1138:
663:
645:
629:
615:
611:
582:
572:
485:
280:
240:
7515:
of Sir John Cadogan giving a lecture on Benzene since Faraday, in 1991
7074:
7008:, 8th edition, Biomedical Publications, Foster City, CA, pp. 144–148,
5768:
5096:
4835:
4818:
4182:
1576:", the radical formed by abstraction of a hydrogen atom from benzene.
1457:
to the manufacture of chemicals with more complex structures, such as
14182:
14047:
13883:
13687:
13567:
13421:
13396:
12841:
12793:
12788:
12773:
12731:
12726:
12684:
12679:
12674:
12632:
12528:
12513:
12453:
12438:
12423:
12243:
12154:
12109:
12074:
12064:
12034:
12029:
12014:
11988:
11950:
11945:
11922:
11917:
11902:
11808:
11803:
11684:
11562:
11552:
11544:
11479:
11456:
11436:
11431:
11401:
11386:
11356:
11338:
11328:
11323:
11318:
11313:
11293:
11278:
11273:
11263:
11258:
11253:
11223:
11198:
11148:
11133:
11128:
11113:
11098:
11078:
11073:
11063:
11053:
11048:
11043:
10963:
10958:
10933:
10863:
10843:
10813:
10735:
10670:
10600:
10590:
10555:
10452:
10356:
10114:
10028:
9993:
9978:
9966:
9809:
9784:
9593:
9154:
8892:
8861:
8851:
8846:
8723:
8451:
8239:
8234:
8013:
6896:
Ashley, DL; Bonin, MA; Cardinali, FL; McCraw, JM; Wooten, JV (1994).
6449:"Advances in Understanding Benzene Health Effects and Susceptibility"
6388:"Advances in understanding benzene health effects and susceptibility"
5952:
5908:
5883:
5859:
5834:
5811:
5173:
4817:
Balaban, Alexandru T.; Schleyer, Paul v. R.; Rzepa, Henry S. (2005).
3774:
Ludwig's Applied Process Design for Chemical And Petrochemical Plants
3421:
an explosion at a China National Petroleum Corporation (CNPC) factory
3228:
3095:
3051:
3047:
2859:
2855:
2804:
2740:
is a general method of derivatizing benzene. Benzene is sufficiently
2647:
2643:
2635:
2627:
2562:
2173:
2157:
2109:
Four chemical processes contribute to industrial benzene production:
1937:
1794:
1430:
1077:
778:
709:
9339:
4861:
1338:
Except where otherwise noted, data are given for materials in their
14150:
14062:
13863:
13726:
13711:
13682:
13551:
13326:
13150:
13094:
13088:
13057:
13002:
12970:
12898:
12831:
12808:
12757:
12753:
12749:
12689:
12663:
12523:
12483:
12463:
12443:
12433:
12373:
12368:
12182:
12144:
12094:
12059:
12024:
12019:
12003:
11998:
11978:
11973:
11968:
11955:
11843:
11651:
11528:
11514:
11489:
11484:
11474:
11446:
11233:
11228:
11208:
11188:
11183:
10983:
10938:
10918:
10883:
10873:
10760:
10715:
10705:
10610:
10505:
10485:
10401:
10122:
10076:
10043:
9739:
9645:
9519:
9474:
9459:
9318:
9313:
9123:
9115:
9107:
8987:
8979:
8971:
8922:
8907:
8897:
8887:
8882:
8856:
8779:
8491:
8471:
8321:
8249:
8244:
8224:
7661:
7559:
7410:"A Former Nazi Labor Camp in Austria, Now Billed as a Tourist Site"
5366:(Braunschweig, Germany: Friedrich Vieweg und Sohn, 1874), vol. 1,
4819:"Crocker, Not Armit and Robinson, Begat the Six Aromatic Electrons"
4789:
The use of a circle to denote a benzene nucleus first appeared in:
4497:
3519:
3287:
3248:
3224:
3204:
2976:
2895:
2829:
2815:
2694:
2500:
2474:
2353:
2216:
2208:
2153:
2138:
2098:
2074:
2070:
2059:
2023:
1808:
In 1929, the cyclic nature of benzene was finally confirmed by the
1735:
1588:
1493:
1450:
1415:
1403:
1318:
1104:
306:
5692:"A Crystallographic Study of Solid Benzene by Neutron Diffraction"
4756:
this view, may be represented by a double ring, in fact." See:
3982:
2601:. In 1988 it was reported that two-thirds of all chemicals on the
188:
14315:
14145:
14098:
14057:
14013:
13950:
13913:
13903:
13898:
13853:
13848:
13788:
13721:
13612:
13607:
13557:
13436:
13426:
13179:
12845:
12835:
12594:
12533:
12508:
12503:
12378:
12338:
12159:
12149:
12134:
12119:
12104:
12089:
12084:
12069:
12054:
11935:
11674:
11534:
10988:
10695:
10396:
10084:
10008:
9859:
9854:
9819:
9804:
9799:
9769:
9752:
9576:
9503:
9469:
9249:
9099:
8944:
8877:
8476:
8466:
8456:
8346:
8336:
8326:
8214:
8180:
8168:
7982:
7972:
7962:
7952:
7502:
5612:
5550:
ten Kate, Inge Loes (June 8, 2018). "Organic molecules on Mars".
3928:
3902:
3383:
Under specific conditions and in the presence of other chemicals
3342:
3239:
to the ring, and the unstable product is immediately reduced (by
3059:
3019:
2871:
2745:
2653:
2606:
2550:
2224:
2204:
2184:
2165:
2149:
2114:
2015:
2011:
1977:
1962:
1900:
1438:
1314:
649:
633:
600:
516:
318:
30:
This article is about the chemical compound. For other uses, see
7267:, Division of Toxicology and Environmental Medicine, August 2007
5417:(Investigations into the structure of di-substituted benzenes),
4531:), presents objections to it, presents an alternative geometry (
4517:
Reports of the Proceedings of the Scientific Society of Freiburg
3845:
2795:
in the presence of a strong Lewis acid catalyst. Similarly, the
1027:
14366:
14187:
14169:
13632:
13602:
13104:
12778:
12741:
12363:
12316:
12187:
12169:
12129:
11813:
11611:
10172:
10104:
9948:
9657:
9650:
9544:
9525:
9514:
9498:
9444:
9144:
9063:
8963:
8912:
8486:
8481:
8461:
8421:
8361:
8356:
8351:
8341:
8331:
8292:
8219:
7997:
7992:
7987:
7977:
7967:
7957:
7922:
7872:
7827:
7709:
7670:
7109:
5516:"Life on Mars? Rover's Latest Discovery Puts It 'On the Table'"
5006:
Image and Reality: Kekule, Kopp, and the Scientific Imagination
3443:
3412:
3279:
3275:
3270:
2E1 (CYP2E1), quinine oxidoreductase (NQ01 or DT-diaphorase or
3236:
3200:
3109:
3091:
3075:. The measurement of benzene in humans can be accomplished via
3043:
3035:
2968:
2919:
2903:
2623:
2614:
2590:
2530:
2504:
2463:
2440:
2137:
with boiling points between 60 and 200 °C is blended with
2055:
2007:
1953:
1949:
1860:
1760:
1739:
1565:
1462:
1419:
1407:
220:
4279:
oily, which benzene is. Thus on page 44, Mitscherlich states:
2778:
13401:
13331:
12139:
10053:
10023:
9956:
9814:
9779:
9774:
9747:
9695:
9662:
9566:
9390:
8828:
8794:
8710:
7762:
4018:
Immediately Dangerous to Life or Health Concentrations (IDLH)
3881:
in Linstrom, Peter J.; Mallard, William G. (eds.);
3064:
2847:
2219:
2122:
1896:
1864:
825:
342:
200:
178:
7528:
6951:
6571:
Rana SV; Verma Y (2005). "Biochemical toxicity of benzene".
6135:"Market Study: Benzene (2nd edition), Ceresana, August 2014"
4870:(in German), vol. 245, no. 1–2, pp. 103–190,
384:
11572:
9481:
6705:"Drinking Water Contaminants | Organic Chemicals | Benzene"
5434:
4458:
4355:
4088:
3497:
Industrial Union Department v. American Petroleum Institute
3485:
3244:
3240:
2639:
1908:
1801:(Journal of the Thirsty Chemical Society), a parody of the
1522:
1279:
1047:
506:
297:
7343:
6895:
6616:
4079:
The word "benzoin" is derived from the Arabic expression "
3883:
2767:
The most widely practiced example of this reaction is the
7183:
6597:
Agency for Toxic Substances and Disease Registry. (2007)
6194:"Control of Hazardous Air Pollutants From Mobile Sources"
6060:
4696:(in German), vol. 162, no. 1, pp. 77–124,
3299:
3055:
3007:
2955:
2631:
2335:
2319:
2306:
2290:
2274:
2261:
2248:
5754:
5211:"The Structure of the Benzene Ring in Hexamethylbenzene"
4095:
Fragrance: The Story of Perfume from Cleopatra to Chanel
6004:"Unicode Character 'BENZENE RING WITH CIRCLE' (U+23E3)"
4247:[On benzol and oily and fatty types of acids].
4245:"Über das Benzol und die Säuren der Oel- und Talgarten"
3680:
3090:
Exposure to benzene may lead progressively to aplastic
2837:
2188:
1051:
10328:
7350:
Environmental Science: Water Research & Technology
6694:. Atsdr.cdc.gov (2011-03-03). Retrieved on 2011-11-23.
6617:
Yardley-Jones, A.; Anderson, D.; Parke, D. V. (1991).
3294:(which maintains chromosome structure), disruption of
2971:
and other illnesses, and is also a notorious cause of
2833:
Friedel-Crafts acylation of benzene by acetyl chloride
12961:
7313:"100 tonnes of pollutants spilled into Chinese river"
6816:
National Institute for Occupational Safety and Health
6317:
5789:
5613:
Eigenbrode, Jennifer L.; et al. (June 8, 2018).
5349: : 166–185; see especially p. 169. From p. 169:
4447:, the lowest known term of which is benzoic acid, … .
4022:
National Institute for Occupational Safety and Health
3989:
National Institute for Occupational Safety and Health
3160:
National Institute for Occupational Safety and Health
2342:{\displaystyle {\ce {C6H5CH3 + H2 -> C6H6 + CH4}}}
2236:
1097:
7147:
6381:
6379:
5697:
Proceedings of the Royal Society of London, Series A
5690:
Bacon, G. E.; Curry, N.; Wilson, S. (May 12, 1964).
4406:
3453:
2791:
of benzene (and many other aromatic rings) using an
1793:
own tail (a symbol in ancient cultures known as the
1043:
7305:
6732:
6730:
3419:, which supplies drinking water to the city, after
2609:, which is used to make polymers and plastics like
2117:hydrodealkylation, toluene disproportionation, and
1441:between the carbon atoms, benzene is classed as an
6104:"A pervasive molecule is captured in a photograph"
5884:"The electronic structure of the benzene molecule"
4535:), and concludes that his alternative is correct (
4407:Hoffman, Augustus W. (1856). "On insolinic acid".
4218:Angewandte Chemie International Edition in English
2874:. Chlorination is achieved with chlorine to give
2807:of benzene (or many other aromatic rings) with an
2341:
1891:, much of benzene was obtained as a by-product of
1031:
12881:Unsorted benzodiazepine site positive modulators:
7025:
6376:
6246:
5480:
5437:Journal of Occupational and Environmental Hygiene
5009:. University of Chicago Press. pp. 186–227.
4713:
4685:"Ueber einige Condensationsproducte des Aldehyds"
2439:A typical reaction yield exceeds 95%. Sometimes,
14435:
6872:Agency for Toxic Substances and Disease Registry
6772:Agency for Toxic Substances and Disease Registry
6727:
6033:"Heterocyclic Chemistry: Heterocyclic Compounds"
5689:
4650:"Sur la constitution des substances aromatiques"
4599:
4242:
3406:
3032:Agency for Toxic Substances and Disease Registry
2183:In similar fashion to this catalytic reforming,
1418:atom attached to each. Because it contains only
330:
7921:
7006:Disposition of Toxic Drugs and Chemicals in Man
6211:
6160:"Market Study: Toluene, Ceresana, January 2015"
5882:Messmer, Richard P.; Schultz, Peter A. (1987).
5074:
4604:[Observations on the aromatic theory].
4160:Philosophical Transactions of the Royal Society
2663:
1844:first applied Gräbe's nomenclature to benzene.
1177:497.78 °C (928.00 °F; 770.93 K)
1120:
164:
6570:
6287:, 16th ed., McGraw-Hill Professional, p. 618,
6249:Ullmann's Encyclopedia of Industrial Chemistry
5881:
5835:"Electronic structure of the benzene molecule"
5483:Ullmann’s Encyclopedia of Industrial Chemistry
5305:
5116:Berichte der Deutschen Chemischen Gesellschaft
4606:Berichte der Deutschen Chemischen Gesellschaft
4452:
3343:Biological oxidation and carcinogenic activity
2761:Electrophilic aromatic substitution of benzene
2462:) is the conversion of toluene to benzene and
1895:production (or "coke-oven light oil") for the
1803:Berichte der Deutschen Chemischen Gesellschaft
1799:Berichte der Durstigen Chemischen Gesellschaft
1163:−11.63 °C (11.07 °F; 261.52 K)
1055:
14474:GABAA receptor positive allosteric modulators
12947:
10314:
9355:
7888:
7686:
7544:
6768:"Benzene Toxicity: Standards and Regulations"
6742:Occupational Safety and Health Administration
6709:United States Environmental Protection Agency
5606:
5543:
5109:
4960:
4907:"Zur Kenntnis der ungesättigen Verbindungen,"
4795:Journal of the Chemical Society, Transactions
4644:
4640:
4638:
4563:Proceedings of the Royal Society of Edinburgh
3660:(86th ed.). Boca Raton (FL): CRC Press.
3153:Occupational Safety and Health Administration
3130:United States Environmental Protection Agency
2719:United States Environmental Protection Agency
2449:
2073:. Replacing one CH with N gives the compound
2006:. Examples of simple benzene derivatives are
954:potential occupational carcinogen, flammable
6795:
6793:
5507:
5425: : 265–301; see especially pp. 299–300.
5251:
5205:
5151:
4859:
4120:
3886:, NIST Standard Reference Database Number 69
3771:Coker, A. Kayode; Ludwig, Ernest E. (2007).
3372:
3286:, and hydroquinone to both benzenetriol and
3058:. The major sources of benzene exposure are
2854:. Sulfonated benzene derivatives are useful
2194:
2022:, respectively. Linking benzene rings gives
1422:and hydrogen atoms, benzene is classed as a
531:5.53 °C (41.95 °F; 278.68 K)
10330:
7524:NLM Hazardous Substances Databank – Benzene
6499:International Agency for Research on Cancer
6226:: Melbourne University Press. p. 347.
5975:"Unicode Character 'BENZENE RING' (U+232C)"
5186:
4682:
4555:
4149:
3846:Atherton Seidell; William F. Linke (1952).
3813:
3811:
3809:
3807:
3805:
3770:
3619:Favre, Henri A.; Powell, Warren H. (2014).
3618:
3614:
3612:
1730:for benzene was long known, but its highly
541:80.1 °C (176.2 °F; 353.2 K)
12954:
12940:
10321:
10307:
9362:
9348:
7895:
7881:
7693:
7679:
7551:
7537:
6285:Harrison's Principles of Internal Medicine
5476:
5474:
4635:
4325:[On a reliable test for benzene].
4215:
3709:
3423:in the city of Jilin on 13 November 2005.
3123:
2988:US Department of Health and Human Services
2521:aromatics (benzene, toluene and xylenes).
1863:. This discovery led to the production of
399:
270:
248:
7361:
7051:
6790:
6642:
6547:
6474:
6464:
6411:
6359:
6349:
6152:
6078:
5907:
5858:
5643:
5581:
5279:
5236:
5049:. New York: Dover Publications. pp.
4932:
4834:
4496:
4172:
3747:
3737:
3649:
3580:Liebig's Annalen der Chemie und Pharmacie
3438:government used benzene administered via
3411:In 2005, the water supply to the city of
3185:
3116:recommends that all workers wear special
2890:, benzene and its derivatives convert to
2697:(petrol) additive, benzene increases the
1980:Consortium has allocated a symbol in the
1610:Historic proposals of benzene structures
366:
7302:, May 19, 2006. Retrieved July 11, 2006.
6466:10.1146/annurev.publhealth.012809.103646
6404:10.1146/annurev.publhealth.012809.103646
6127:
5930:
5757:Journal of the American Chemical Society
5549:
5380:"Ueber die Constitution des Naphthalins"
5306:Ramos-Figueroa, Josseline (2021-05-21).
4967:Liebigs Annalen der Chemie und Pharmacie
4654:Bulletin de la Société Chimique de Paris
4323:"Ueber eine sichere Reaction auf Benzol"
4116:
4114:
4097:. Charles Scribner's Sons. p. 101.
3983:NIOSH Pocket Guide to Chemical Hazards.
3950:
3948:
3946:
3802:
3609:
3164:Immediately Dangerous to Life and Health
2954:
2862:, benzene reacts with nitronium ions (NO
2828:
2756:
2688:
2659:
1924:
7484:International Chemical Safety Card 0015
6808:Department of Health and Human Services
6738:"Chemical Sampling Information Benzene"
5832:
5471:
4762:"The structure of cycloid hydrocarbons"
4320:
3978:
3976:
3974:
3325:
1929:The various representations of benzene.
395:
14:
14436:
7494:NIOSH Pocket Guide to Chemical Hazards
7296:"FDA: Too Much Benzene In Some Drinks"
6623:British Journal of Industrial Medicine
6521:
6102:Browne, Malcolm W. (August 16, 1988),
6101:
4602:"Bemerkungen zur aromatischen Theorie"
4092:
3874:
3872:
3870:
3841:
3839:
3777:. Vol. 1. Elsevier. p. 114.
3251:. The catechol is then metabolized to
3144:. The maximum contaminant level goal (
3071:tubes, which are then analyzed with a
3025:
2617:and acetone for resins and adhesives.
2356:(aka diphenyl) at higher temperature:
2128:
1987:
261:
12935:
10302:
9369:
9343:
7876:
7674:
7532:
6868:"Public Health Statement for Benzene"
6818:(NIOSH). October 2004. Archived from
6446:
6385:
5513:
5481:Hillis O. Folkins (2005). "Benzene".
5002:
4111:
3943:
3658:CRC Handbook of Chemistry and Physics
3354:
3218:
2133:In catalytic reforming, a mixture of
2085:N. Although benzene and pyridine are
1847:
1525:material was derived from benzoin by
427:Key: UHOVQNZJYSORNB-UHFFFAOYSA-N
228:
208:
12922:GABA metabolism/transport modulators
6675:. Osha.gov. Retrieved on 2011-11-23.
6323:
6116:from the original on August 12, 2021
5671:from the original on August 25, 2021
5397: : 20–28; see especially p. 26.
5040:
4358:"Untersuchung des Steinkohlentheers"
4356:Mansfield Charles Blachford (1849).
4060:
3971:
3655:
3586:(1): 77–124, 309–320. From p. 89:
3553:
2838:Sulfonation, chlorination, nitration
1742:atom, was challenging to determine.
1445:. Benzene is a colorless and highly
1429:Benzene is a natural constituent of
12539:Trichloroethane (methyl chloroform)
7177:
7141:
7103:
7028:"An overview of benzene metabolism"
6599:Benzene: Patient information sheet.
6095:
5389:(On the structure of naphthalene),
4862:"Über die Constitution des Benzols"
4767:Proceedings of the Chemical Society
3867:
3836:
2801:electrophilic aromatic substitution
2738:Electrophilic aromatic substitution
1410:atoms joined in a planar hexagonal
321:
305:
72:Skeletal formula detail of benzene.
24:
14326:Nexus for Exoplanet System Science
11602:11-Methoxy-12-hydroxydehydrokavain
7378:"Selections and lethal injections"
7325:from the original on 10 March 2020
6801:"NIOSH respirator selection logic"
4917:Justus Liebig’s Annalen der Chemie
4889:Justus Liebig’s Annalen der Chemie
4333:(2): 200–205, especially 204–205.
3627:. pp. 10, 22, 204, 494, 577.
3259:, used by organisms mainly in the
2913:
2850:, a mixture of sulfuric acid with
2744:that it undergoes substitution by
2018:, abbreviated PhOH, PhMe, and PhNH
1856:popularized the use of benzene to
1116:
424:InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
80:
67:
25:
14545:
14226:Atomic and molecular astrophysics
12963:Molecules detected in outer space
12349:Acetylglycinamide chloral hydrate
7489:USEPA Summary of Benzene Toxicity
7436:
7420:from the original on May 11, 2019
5528:from the original on May 28, 2019
4867:Justus Liebigs Annalen der Chemie
3442:as one of their many methods for
3337:fluorescent in situ hybridization
3272:NAD(P)H dehydrogenase (quinone 1)
2950:
2752:to give substituted derivatives.
2545:to benzene. The reaction of the
2491:
1819:methods. Using large crystals of
14416:
14404:
14392:
14381:
14380:
13187:
13178:
13169:
7902:
7700:
7443:
7402:
7390:from the original on May 9, 2020
7370:
7337:
7289:
7270:
7258:Public Health Statement. Benzene
7251:
7232:
7220:
5419:Annalen der Chemie und Pharmacie
5391:Annalen der Chemie und Pharmacie
5259:Proceedings of the Royal Society
5216:Proceedings of the Royal Society
4693:Annalen der Chemie und Pharmacie
4523: : 116–381. In the section
4410:Proceedings of the Royal Society
4362:Annalen der Chemie und Pharmacie
4345:from the original on 2015-11-22.
4327:Annalen der Chemie und Pharmacie
4294:Annales de Chemie et de Physique
3470:
3456:
3302:strand breaks, and altering DNA
2881:
2777:
2524:
1776:
1693:
1686:
1679:
1661:
1629:
1622:
1615:
1556:. He gave the compound the name
1346:
997:
992:
987:
982:
977:
475:
99:
50:
14351:Polycyclic aromatic hydrocarbon
12769:Menthyl isovalerate (validolum)
7383:Auschwitz-Birkenau State Museum
7068:
7026:Snyder, R; Hedli, C.C. (1996).
7019:
6998:
6985:
6955:Chemico-Biological Interactions
6945:
6934:from the original on 2011-11-22
6889:
6878:from the original on 2012-01-20
6860:
6830:
6810:(DHHS), Public Health Service,
6760:
6697:
6678:
6659:
6610:
6591:
6564:
6515:
6512:, Volumes 1 to 42, Supplement 7
6491:
6447:Smith, Martyn T. (2010-01-01).
6440:
6428:
6298:
6273:
6240:
6186:
6177:
6141:from the original on 2017-12-21
6054:
6043:from the original on 2016-04-06
6025:
6014:from the original on 2009-07-03
5996:
5985:from the original on 2009-02-19
5967:
5924:
5875:
5826:
5783:
5748:
5683:
5514:Chang, Kenneth (June 7, 2018).
5428:
5400:
5372:
5364:Neues Handwörterbuch der Chemie
5356:
5324:
5299:
5288:from the original on 2021-03-19
5245:
5199:
5180:
5145:
5134:from the original on 2007-05-16
5103:
5067:
5034:
5023:from the original on 2020-07-27
4996:
4985:from the original on 2021-12-26
4954:
4943:from the original on 2016-05-07
4926:
4881:
4853:
4778:from the original on 2021-11-16
4749:
4738:from the original on 2015-10-22
4720:Journal of the Chemical Society
4707:
4676:
4664:from the original on 2015-11-14
4624:from the original on 2015-11-22
4593:
4582:from the original on 2015-11-24
4549:
4504:
4400:
4391:
4380:from the original on 2015-10-27
4349:
4314:
4286:
4269:from the original on 2015-11-23
4236:
4209:
4189:from the original on 2020-11-21
4143:
4073:
4054:
4028:
4006:
3995:
3917:
3856:from the original on 2020-03-11
3825:from the original on 2014-05-29
3791:from the original on 2016-03-12
3560:
2846:of benzene involves the use of
1826:
1602:
1437:. Due to the cyclic continuous
1342:(at 25 °C , 100 kPa).
11718:Allopregnanolone (brexanolone)
6453:Annual Review of Public Health
6162:. ceresana.com. Archived from
3891:
3764:
3703:
3674:
2967:, which increases the risk of
2293:
1718:Friedrich Karl Johannes Thiele
1560:. In 1836, the French chemist
941:Occupational safety and health
469:
13:
1:
14276:Extraterrestrial liquid water
12914:Receptor/signaling modulators
11470:Ampelopsin (dihydromyricetin)
7558:
6257:10.1002/14356007.a10_035.pub2
5154:Journal of Chemical Education
5077:Journal of Chemical Education
4477:Astrophysical Journal Letters
3710:Breslow, R.; Guo, T. (1990).
3602:
3407:Contamination of water supply
3359:
3180:
2996:acute nonlymphocytic leukemia
2499:is the process for producing
2104:
1882:
1433:and is one of the elementary
1247:(US health exposure limits):
12664:ergoloid (dihydroergotoxine)
11749:anabolic-androgenic steroids
10531:Butabarbital/Secbutabarbital
10336:receptor positive modulators
7477:The Periodic Table of Videos
7163:10.1016/0165-1218(94)90028-0
7127:10.1016/j.toxlet.2009.04.028
7089:10.1016/j.toxlet.2008.09.008
6351:10.1371/journal.pone.0100307
6220:Chemistry: A structural view
6080:10.1016/j.catcom.2022.106541
4905:See further: Thiele (1901)
4061:Shao, Elena (28 June 2022).
2984:American Petroleum Institute
2803:. The reaction involves the
2731:
2537:can be reduced with metals.
2164:with any one of a number of
1956:, which has 14. Benzene and
1914:
1700:
1668:
1636:
1606:
1504:
1480:. Its particular effects on
1453:. It is used primarily as a
85:Benzene ball-and-stick model
7:
13507:Protonated hydrogen cyanide
11304:Triflunordazepam (Ro5-2904)
6842:Centers for Disease Control
6812:Centers for Disease Control
6039:, Department of Chemistry.
4475:, and Benzene in CRL 618",
3449:
3429:
3172:recommended exposure limits
2963:Benzene is classified as a
1581:Charles Blachford Mansfield
1476:Benzene is classified as a
1231:44,000 ppm (rabbit, 30 min)
1195:or concentration (LD, LC):
654:20 °C, solution in acetone:
638:20 °C, solution in ethanol:
567:17.8 g/kg (200 °C, 40 MPa)
565:21.7 g/kg (200 °C, 6.5 MPa)
106:Benzene at room temperature
63:
10:
14550:
11632:5,6,7,8-Tetrahydroyangonin
7480:(University of Nottingham)
7186:J Toxicol Environ Health A
6917:10.1093/clinchem/40.7.1401
6885:– via Atsdr.cdc.gov.
6528:Int J Occup Environ Health
6305:Merck Manual, Home Edition
5362:Hermann von Fehling, ed.,
4714:Armstrong Henry E (1887).
4296:, vol. 63, pp. 27–45, see
3968:. Retrieved on 2014-05-29.
3625:Royal Society of Chemistry
3376:
2450:Toluene disproportionation
2141:gas and then exposed to a
1991:
1918:
1585:August Wilhelm von Hofmann
1499:
1237:20,000 ppm (human, 5 min)
138:Annulene (not recommended)
36:
29:
14375:
14266:Earliest known life forms
14261:Diffuse interstellar band
14201:
14121:
14046:
13937:
13872:
13812:
13740:
13732:Protonated cyanoacetylene
13646:
13540:
13502:Protonated carbon dioxide
13462:Hydromagnesium isocyanide
13410:
13196:
13167:
12978:
12969:
12907:
12557:
12325:
12262:
12229:
12196:
12168:
11882:
11824:Pregnanolone (eltanolone)
11703:
11660:
11571:
11543:
11455:
11337:
10779:
10466:
10367:Chlorobutanol (cloretone)
10342:
10257:
10216:
10136:
10113:
10075:
10052:
9947:
9868:
9738:
9715:
9671:
9614:
9537:
9512:
9377:
9306:
9268:
9242:
9207:
9163:
9135:
9098:
9089:
9056:
9028:
9019:
8999:
8962:
8953:
8935:
8870:
8827:
8818:
8807:
8762:
8709:
8656:
8638:
8598:
8545:
8500:
8444:
8420:
8370:
8314:
8291:
8278:
8258:
8190:
8159:
8119:
8066:
8006:
7945:
7910:
7849:
7826:
7761:
7708:
7654:
7623:
7566:
7198:10.1080/15287390802349974
6971:10.1016/j.cbi.2005.03.031
6827:publication No. 2005-100.
6806:. Cincinnati, Ohio: U.S.
6540:10.1179/oeh.2007.13.2.213
6386:Smith, Martyn T. (2010).
6314:, "Overview of Leukemia".
6037:Michigan State University
5449:10.1080/15459620701446642
5128:10.1002/cber.189002301204
5045:From alchemy to chemistry
4600:Ladenburg Albert (1869).
4576:10.1017/S0370164600045387
4525:Aromatischen Verbindungen
4243:Mitscherlich, E. (1834).
4137:10.1080/00033798500200411
4093:Morris, Edwin T. (1984).
3925:"Benzenide (CID 5150480)"
3899:"Benzenium (CID 12533897"
3656:Lide, D. R., ed. (2005).
3401:World Health Organization
3373:Exposure from soft drinks
3134:maximum contaminant level
2902:, such as finely divided
2789:Friedel-Crafts alkylation
2603:American Chemical Society
2195:Toluene hydrodealkylation
1734:structure, with just one
1669:
1660:
1609:
1471:volatile organic compound
1336:
1329:
1324:
1303:
1241:
1191:
958:
938:
933:
831:
797:
456:
436:
411:
148:
128:
116:
111:
98:
62:
49:
14529:Sweet-smelling chemicals
14489:IARC Group 1 carcinogens
14479:Hazardous air pollutants
14311:Iron–sulfur world theory
14306:Photodissociation region
14009:Methyl-cyano-diacetylene
12918:GABA receptor modulators
12828:sulfonmethane (sulfonal)
6067:Catalysis Communications
5491:10.1002/14356007.a03_475
4979:10.1002/jlac.18661370202
4876:10.1002/jlac.18882450110
4760:Armstrong, H.E. (1890).
4702:10.1002/jlac.18721620110
4618:10.1002/cber.18690020171
4374:10.1002/jlac.18490690203
4339:10.1002/jlac.18450550205
4263:10.1002/jlac.18340090103
2918:Benzene is an excellent
2799:is a related example of
2797:Friedel-Crafts acylation
2565:gives benzene. Complete
1587:, isolated benzene from
1490:Boston metropolitan area
1325:Supplementary data page
1273:Ca TWA 0.1 ppm ST 1 ppm
1072:Precautionary statements
37:Not to be confused with
32:Benzene (disambiguation)
14386:Category:Astrochemistry
13976:, fullerene, buckyball)
13663:Cyanobutadiynyl radical
13638:Silicon-carbide cluster
13628:Protonated formaldehyde
10268:chemical classification
7277:Benzene, CASRN: 71-43-2
7044:10.1289/ehp.96104s61165
7032:Environ Health Perspect
5833:Pauling, Linus (1987).
5645:10.1126/science.aas9185
5574:10.1126/science.aat2662
5485:. Weinheim: Wiley-VCH.
5330:Wilhelm Körner (1867)
4539:). See also figures on
4321:Hofmann, A. W. (1845).
3263:for energy production.
3213:1,2,4-trihydroxybenzene
3124:Benzene exposure limits
2900:heterogeneous catalysts
2576:
1982:Miscellaneous Technical
1790:German Chemical Society
1756:Friedrich August Kekulé
1640:Adolf Karl Ludwig Claus
745:Magnetic susceptibility
14399:Outer space portal
14241:Circumstellar envelope
13206:Aluminium(I) hydroxide
13116:Phosphorus mononitride
12993:Aluminium monofluoride
12988:Aluminium monochloride
12804:Retigabine (ezogabine)
12080:Lirequinil (Ro41-3696)
11647:7,8-Dihydromethysticin
11637:5,6-Dehydromethysticin
10516:Benzylbutylbarbiturate
9230:1,3,5-Triheptylbenzene
7602:Cyclotetradecaheptaene
7038:(Suppl 6): 1165–1171.
6744:(OSHA). Archived from
6392:Annu Rev Public Health
5718:10.1098/rspa.1964.0092
5281:10.1098/rspa.1931.0166
5238:10.1098/rspa.1929.0081
5110:Kekulé, F. A. (1890).
4961:Kekulé, F. A. (1866).
4933:Loschmidt, J. (1861).
4423:10.1098/rspl.1856.0002
4230:10.1002/anie.196803451
4174:10.1098/rstl.1825.0022
3884:NIST Chemistry WebBook
3379:Benzene in soft drinks
3316:phenylmercapturic acid
3197:phenylmercapturic acid
3186:Biomarkers of exposure
2992:acute myeloid leukemia
2960:
2834:
2762:
2685:
2541:and its salts undergo
2509:aliphatic hydrocarbons
2469:Given that demand for
2343:
2121:etc. According to the
1930:
1905:petrochemical industry
1748:Johann Josef Loschmidt
1744:Archibald Scott Couper
1704:Henry Edward Armstrong
1597:detected in deep space
1535:bicarburet of hydrogen
1213:930 mg/kg (rat, oral)
1127:
658:49.4 mL/L (62.5% v/v)
656:7.69 mL/L (38.46% v/v)
86:
73:
14514:Simple aromatic rings
14454:Aromatic hydrocarbons
14296:Interplanetary medium
14271:Extraterrestrial life
13909:Octatetraynyl radical
13527:Tricarbon monosulfide
13074:Magnesium monohydride
10275:chemical nomenclature
9225:1,3,5-Triethylbenzene
6844:(CDC). Archived from
6711:(EPA). Archived from
5252:Lonsdale, K. (1931).
5003:Rocke, A. J. (2010).
4860:Adolf Baeyer (1888),
4250:Annalen der Pharmacie
3739:10.1073/pnas.87.1.167
3633:10.1039/9781849733069
3491:1,2,3-Cyclohexatriene
3393:Food Standards Agency
3387:(a preservative) and
3042:, and fabrication of
2958:
2832:
2760:
2689:Component of gasoline
2683:
2344:
1994:Aromatic hydrocarbons
1928:
1496:in some individuals.
1126:
624:7.61 g/100 g (60 °C)
84:
71:
14484:Hydrocarbon solvents
14423:Chemistry portal
14411:Astronomy portal
14357:RNA world hypothesis
14341:PAH world hypothesis
14034:Heptatrienyl radical
13966:Buckminsterfullerene
13854:Methylcyanoacetylene
13362:Silicon carbonitride
13337:Methylidynephosphane
13303:Magnesium isocyanide
13211:Aluminium isocyanide
13013:Carbon monophosphide
12859:constituents (e.g.,
12643:Deuterated etifoxine
11705:Neuroactive steroids
11675:Apronal (apronalide)
11527:constituents (e.g.,
11144:N-Desalkylflurazepam
8628:Isopropylcyclohexene
8210:Perhydrophenanthrene
8149:Isopropylcyclohexane
7614:Cyclooctadecanonaene
7608:Cyclohexadecaoctaene
7321:. 25 November 2005.
7239:ToxGuide for Benzene
6635:10.1136/oem.48.7.437
5406:Victor Meyer (1870)
5073:English translation
4807:10.1039/ct9252701604
4732:10.1039/ct8875100258
4683:Aug. Kekulé (1872),
4556:Dewar James (1869).
4036:"Benzene fact sheet"
3326:Molecular toxicology
3162:(NIOSH) revised the
2870:is the precursor to
2559:Alkyne trimerisation
2234:
1967:resonance structures
1539:Eilhard Mitscherlich
1443:aromatic hydrocarbon
1260:TWA 1 ppm, ST 5 ppm
1109:(fire diamond)
622:6.61 g/100 g (40 °C)
620:5.83 g/100 g (20 °C)
118:Preferred IUPAC name
89:Ball and stick model
27:Hydrocarbon compound
14469:Commodity chemicals
14301:Interstellar medium
14281:Forbidden mechanism
14094:Hydrogen isocyanide
13784:Hexatriynyl radical
13367:c-Silicon dicarbide
13272:Hydrogen isocyanide
13136:Silicon monosulfide
13111:Phosphorus monoxide
13079:Methylidyne radical
13038:Fluoromethylidynium
12998:Aluminium(II) oxide
12652:dihydroergocryptine
11964:Pyrazolopyrimidines
11622:5,6-Dihydroyangonin
11607:7,8-Dihydroyangonin
10794:3-Hydroxyphenazepam
10636:Methylphenobarbital
9731:not C, H or O)
9324:Alicyclic compounds
9137:Tetramethylbenzenes
7804:1,4-Cycloheptadiene
7799:1,3-Cycloheptadiene
7227:ToxFAQs for Benzene
6963:2005CBI...153..253F
6825:on August 29, 2017.
6715:on February 2, 2015
6342:2014PLoSO...9j0307B
5945:1987Natur.329..491H
5900:1987Natur.329..492M
5851:1987Natur.325..396P
5804:1986Natur.323..699C
5710:1964RSPSA.279...98B
5636:2018Sci...360.1096E
5630:(6393): 1096–1101.
5566:2018Sci...360.1068T
5560:(6393): 1068–1069.
5272:1931RSPSA.133..536L
5229:1929RSPSA.123..494L
5166:1958JChEd..35...21B
5089:1965JChEd..42..266W
5041:Read, John (1995).
4489:2001ApJ...546L.123C
3730:1990PNAS...87..167B
3697:10.1021/i460004a016
3168:breathing apparatus
3118:breathing equipment
3054:, medications, and
3026:Exposure to benzene
2973:bone marrow failure
2898:in the presence of
2555:hypophosphorus acid
2337:
2321:
2308:
2292:
2276:
2263:
2250:
2129:Catalytic reforming
2111:catalytic reforming
1988:Benzene derivatives
1831:The German chemist
1467:industrial chemical
1406:is composed of six
1331:Benzene (data page)
672:52 g/100 g (20 °C)
640:1.2 mL/L (20% v/v)
548:Solubility in water
493: g·mol
57:Space-filling model
46:
14524:Soil contamination
14519:Six-membered rings
14321:Molecules in stars
14291:Intergalactic dust
14236:Circumstellar dust
14178:Naphthalene cation
14113:Trihydrogen cation
14089:Hydrogen deuteride
14014:Methyltriacetylene
13849:Hexapentaenylidene
13668:E-Cyanomethanimine
13588:Cyclopropenylidene
13522:Tricarbon monoxide
13512:Silicon tricarbide
13482:Methylene amidogen
13472:Isothiocyanic acid
13387:Thioxoethenylidene
13347:Trihydrogen cation
13161:Titanium(II) oxide
13121:Potassium chloride
13100:Sulfur mononitride
13043:Helium hydride ion
13018:Carbon monosulfide
12746:4-O-methylhonokiol
12409:Dichloralphenazone
12307:Methylmethaqualone
11884:Nonbenzodiazepines
11597:Desmethoxyyangonin
11592:11-Hydroxyyangonin
11587:11-Methoxyyangonin
11582:10-Methoxyyangonin
10969:Ethyl carfluzepate
10571:Cyclopentobarbital
10173:Hypervalent iodine
9281:Cyclopropenylidene
8618:Methylcyclopentene
8608:Methylcyclopropene
8139:Methylcyclopentane
8129:Methylcyclopropane
7816:1,5-Cyclooctadiene
7789:1,4-Cyclohexadiene
7784:1,3-Cyclohexadiene
7596:Cyclododecahexaene
7363:10.1039/D0EW00836B
7282:2011-10-22 at the
7263:2010-05-27 at the
7244:2010-05-28 at the
7077:Toxicology Letters
7004:Baselt, R. (2008)
6993:2009 TLVs and BEIs
6957:. 153–154: 253–6.
6911:(7 Pt 2): 1401–4.
6905:Clinical Chemistry
6690:2010-05-28 at the
6671:2015-06-29 at the
6604:2014-12-15 at the
6508:2008-03-06 at the
6310:2011-09-29 at the
6109:The New York Times
5521:The New York Times
5337:2017-07-07 at the
5112:"Benzolfest: Rede"
4912:2021-12-26 at the
4901:2020-03-10 at the
4894:: 87–142; see:
4303:2015-03-20 at the
4067:The New York Times
4042:. 2 September 2021
3964:2016-12-01 at the
3905:. February 8, 2007
3574:2020-03-20 at the
3464:Environment portal
3355:Routes of exposure
3235:enzyme can add an
3219:Biotransformations
3069:activated charcoal
3010:strand breaks and
2961:
2835:
2824:Iron(III) chloride
2820:aluminium chloride
2763:
2686:
2547:diazonium compound
2514:pyrolysis gasoline
2456:disproportionation
2339:
2325:
2309:
2296:
2280:
2264:
2251:
2238:
1931:
1848:Early applications
1769:arene substitution
1486:The New York Times
1369:Infobox references
1304:Related compounds
1282:(Immediate danger)
1128:
793:0.3075 cP (80 °C)
87:
74:
44:
14459:Aromatic solvents
14431:
14430:
14346:Pseudo-panspermia
14042:
14041:
13989:Cyanodecapentayne
13929:N-Methylformamide
13904:Methyldiacetylene
13829:Aminoacetonitrile
13799:Methyl isocyanate
13717:Methyl isocyanide
13598:Isocyanoacetylene
13578:Cyanoformaldehyde
13457:Hydrogen peroxide
13342:Potassium cyanide
13298:Magnesium cyanide
13251:Disilicon carbide
13246:Dicarbon monoxide
13053:Hydrogen fluoride
13048:Hydrogen chloride
12929:
12928:
12889:MRK-409 (MK-0343)
12660:dihydroergotamine
12603:potassium bromide
12597:compounds (e.g.,
12544:Trichloroethylene
12312:Nitromethaqualone
12231:Pyrazolopyridines
11733:3α-Androstanediol
11627:7,8-Dihydrokavain
10979:Ethyl loflazepate
10756:Thiotetrabarbital
10372:Ethanol (alcohol)
10296:
10295:
10234:Sulfenyl chloride
10212:
10211:
9711:
9710:
9530:(only C, H and O)
9371:Functional groups
9337:
9336:
9302:
9301:
9238:
9237:
9215:Hexamethylbenzene
9203:
9202:
9085:
9084:
9030:Trimethylbenzenes
9015:
9014:
8931:
8930:
8803:
8802:
8790:Cyclododecatriene
8785:Cyclooctatetraene
8623:Methylcyclohexene
8613:Methylcyclobutene
8600:Alkylcycloalkenes
8541:
8540:
8416:
8415:
8274:
8273:
8144:Methylcyclohexane
8134:Methylcyclobutane
8121:Alkylcycloalkanes
8062:
8061:
7870:
7869:
7862:Cyclononatetraene
7857:Cyclooctatetraene
7668:
7667:
7646:Cyclononatetraene
7591:Cyclodecapentaene
7586:Cyclooctatetraene
7519:Substance profile
7192:(22): 1482–1489.
6279:Kasper, Dennis L.
6233:978-0-522-83988-3
6224:Carlton, Victoria
5939:(6139): 491–492.
5798:(6090): 699–701.
5769:10.1021/ja0630285
5097:10.1021/ed042p266
4936:Chemische Studien
4836:10.1021/cr0300946
4829:(10): 3436–3447.
4124:Annals of Science
3784:978-0-7506-7766-0
3642:978-0-85404-182-4
3623:. Cambridge: The
3554:Explanatory notes
3278:(benzene oxide),
3261:citric acid cycle
3073:gas chromatograph
3030:According to the
3014:damage, hence is
2328:
2312:
2299:
2283:
2267:
2254:
2241:
2201:hydrodealkylation
2170:diethylene glycol
2146:platinum chloride
1934:X-ray diffraction
1821:hexamethylbenzene
1817:X-ray diffraction
1813:Kathleen Lonsdale
1728:empirical formula
1724:
1723:
1392:molecular formula
1388:chemical compound
1377:Chemical compound
1375:
1374:
1310:Related compounds
1292:Safety data sheet
1022:Hazard statements
791:0.4965 cP (40 °C)
789:0.6076 cP (25 °C)
699:181 kPa (100 °C)
668:diethylene glycol
563:3.94 g/L (100 °C)
501:Colorless liquid
380:CompTox Dashboard
190:Interactive image
133:(historic/German)
94:
93:
39:Petroleum benzine
16:(Redirected from
14541:
14504:Chemical hazards
14421:
14420:
14419:
14409:
14408:
14407:
14397:
14396:
14395:
14384:
14383:
14331:Organic compound
14231:Chemical formula
14136:Dihydroxyacetone
14084:Hydrogen cyanide
13769:Cyanodiacetylene
13623:Propadienylidene
13517:Thioformaldehyde
13392:Titanium dioxide
13357:Sodium hydroxide
13278:Hydrogen sulfide
13266:Hydrogen cyanide
13226:Carbonyl sulfide
13191:
13182:
13173:
13131:Silicon monoxide
13064:Hydroxyl radical
12976:
12975:
12956:
12949:
12942:
12933:
12932:
12648:Dihydroergolines
12565:3-Hydroxybutanal
12198:Piperidinediones
11931:Imidazopyridines
11465:6-Methylapigenin
11397:Hydroxyphenamate
11269:SH-053-R-CH3-2′F
10974:Ethyl dirazepate
10854:Chlordiazepoxide
10746:Thiobutabarbital
10458:Trifluoroethanol
10448:Trichloroethanol
10438:-Pentanol (2M2B)
10332:
10323:
10316:
10309:
10300:
10299:
10263:
10168:Trifluoromethoxy
9736:
9735:
9732:
9535:
9534:
9531:
9384:
9364:
9357:
9350:
9341:
9340:
9294:-Propenylbenzene
9096:
9095:
9026:
9025:
8960:
8959:
8951:
8950:
8825:
8824:
8816:
8815:
8501:Branched alkynes
8442:
8441:
8371:Branched alkenes
8312:
8311:
8289:
8288:
8192:Polycycloalkanes
8177:(bicycloheptane)
8171:(bicyclopentane)
8007:Branched alkanes
7943:
7942:
7919:
7918:
7897:
7890:
7883:
7874:
7873:
7841:Cycloheptatriene
7795:Cycloheptadiene
7695:
7688:
7681:
7672:
7671:
7641:Cycloheptatriene
7553:
7546:
7539:
7530:
7529:
7447:
7446:
7430:
7429:
7427:
7425:
7406:
7400:
7399:
7397:
7395:
7374:
7368:
7367:
7365:
7341:
7335:
7334:
7332:
7330:
7309:
7303:
7293:
7287:
7274:
7268:
7255:
7249:
7236:
7230:
7224:
7218:
7217:
7181:
7175:
7174:
7145:
7139:
7138:
7107:
7101:
7100:
7072:
7066:
7065:
7055:
7023:
7017:
7002:
6996:
6989:
6983:
6982:
6949:
6943:
6942:
6940:
6939:
6933:
6902:
6893:
6887:
6886:
6884:
6883:
6864:
6858:
6857:
6855:
6853:
6848:on July 22, 2012
6834:
6828:
6826:
6824:
6805:
6797:
6788:
6787:
6785:
6783:
6778:on June 10, 2010
6764:
6758:
6757:
6755:
6753:
6748:on June 29, 2015
6734:
6725:
6724:
6722:
6720:
6701:
6695:
6682:
6676:
6663:
6657:
6656:
6646:
6614:
6608:
6595:
6589:
6588:
6568:
6562:
6561:
6551:
6519:
6513:
6495:
6489:
6488:
6478:
6468:
6444:
6438:
6432:
6426:
6425:
6415:
6383:
6374:
6373:
6363:
6353:
6324:Bard, D (2014).
6321:
6315:
6302:
6296:
6277:
6271:
6270:
6244:
6238:
6237:
6215:
6209:
6208:
6206:
6205:
6190:
6184:
6181:
6175:
6174:
6172:
6171:
6156:
6150:
6149:
6147:
6146:
6137:. ceresana.com.
6131:
6125:
6124:
6123:
6121:
6099:
6093:
6092:
6082:
6058:
6052:
6051:
6049:
6048:
6029:
6023:
6022:
6020:
6019:
6000:
5994:
5993:
5991:
5990:
5971:
5965:
5964:
5953:10.1038/329491b0
5928:
5922:
5921:
5911:
5909:10.1038/329492a0
5879:
5873:
5872:
5862:
5860:10.1038/325396d0
5830:
5824:
5823:
5812:10.1038/323699a0
5787:
5781:
5780:
5752:
5746:
5745:
5704:(1376): 98–110.
5687:
5681:
5680:
5678:
5676:
5670:
5647:
5619:
5610:
5604:
5603:
5585:
5547:
5541:
5540:
5535:
5533:
5511:
5505:
5504:
5478:
5469:
5468:
5432:
5426:
5404:
5398:
5376:
5370:
5360:
5354:
5328:
5322:
5321:
5319:
5318:
5303:
5297:
5296:
5294:
5293:
5283:
5266:(822): 536–553.
5249:
5243:
5242:
5240:
5223:(792): 494–515.
5203:
5197:
5196:
5184:
5178:
5177:
5174:10.1021/ed035p21
5149:
5143:
5142:
5140:
5139:
5107:
5101:
5100:
5071:
5065:
5064:
5048:
5038:
5032:
5031:
5029:
5028:
5000:
4994:
4993:
4991:
4990:
4958:
4952:
4951:
4949:
4948:
4930:
4924:
4885:
4879:
4878:
4857:
4851:
4848:
4838:
4823:Chemical Reviews
4810:
4786:
4784:
4783:
4753:
4747:
4746:
4744:
4743:
4711:
4705:
4704:
4689:
4680:
4674:
4672:
4670:
4669:
4642:
4633:
4632:
4630:
4629:
4597:
4591:
4590:
4588:
4587:
4553:
4547:
4508:
4502:
4501:
4500:
4483:(2): L123–L126,
4456:
4450:
4449:
4404:
4398:
4395:
4389:
4388:
4386:
4385:
4353:
4347:
4346:
4318:
4312:
4290:
4284:
4277:
4275:
4274:
4240:
4234:
4233:
4213:
4207:
4197:
4195:
4194:
4176:
4147:
4141:
4140:
4118:
4109:
4108:
4077:
4071:
4070:
4058:
4052:
4051:
4049:
4047:
4032:
4026:
4025:
4010:
4004:
3999:
3993:
3992:
3980:
3969:
3952:
3941:
3940:
3938:
3936:
3921:
3915:
3914:
3912:
3910:
3895:
3889:
3876:
3865:
3864:
3862:
3861:
3852:. Van Nostrand.
3843:
3834:
3833:
3831:
3830:
3815:
3800:
3799:
3797:
3796:
3768:
3762:
3761:
3751:
3741:
3707:
3701:
3700:
3678:
3672:
3671:
3653:
3647:
3646:
3616:
3596:
3564:
3480:
3475:
3474:
3473:
3466:
3461:
3460:
3292:topoisomerase II
3100:multiple myeloma
3040:synthetic fibers
3038:, production of
2781:
2662:
2431:
2430:
2429:
2421:
2420:
2412:
2411:
2403:
2402:
2392:
2391:
2390:
2380:
2379:
2378:
2370:
2369:
2348:
2346:
2345:
2340:
2338:
2336:
2333:
2326:
2320:
2317:
2310:
2307:
2304:
2297:
2291:
2288:
2281:
2275:
2272:
2265:
2262:
2259:
2252:
2249:
2246:
2239:
2004:functional group
1810:crystallographer
1780:
1711:Adolf von Baeyer
1697:
1690:
1683:
1665:
1654:Albert Ladenburg
1633:
1626:
1619:
1607:
1583:, working under
1513:" derives from "
1359:
1353:
1350:
1349:
1235:52,308 ppm (cat)
1233:44,923 ppm (dog)
1225:lowest published
1183:Explosive limits
1148:
1141:
1134:
1119:
1099:
1095:
1091:
1087:
1083:
1079:
1065:
1061:
1057:
1053:
1049:
1045:
1041:
1037:
1033:
1029:
1001:
996:
991:
986:
981:
925:
898:
871:
847:
832:Thermochemistry
758:Refractive index
751:−54.8·10 cm/mol
697:24.4 kPa (40 °C)
695:12.7 kPa (25 °C)
561:2.26 g/L (61 °C)
559:1.84 g/L (30 °C)
557:1.79 g/L (15 °C)
521:0.8765(20) g/cm
492:
477:
471:
464:Chemical formula
404:
403:
388:
386:
370:
334:
323:
309:
282:
274:
263:
252:
232:
212:
192:
168:
103:
64:
54:
47:
43:
21:
14549:
14548:
14544:
14543:
14542:
14540:
14539:
14538:
14434:
14433:
14432:
14427:
14417:
14415:
14405:
14403:
14393:
14391:
14371:
14197:
14173:
14164:
14117:
14107:
14050:
14038:
14019:Propionaldehyde
13994:Ethylene glycol
13983:
13975:
13971:
13942:
13940:
13933:
13889:Cyanohexatriyne
13875:
13868:
13815:
13808:
13743:
13736:
13696:
13649:
13642:
13613:Methoxy radical
13543:
13536:
13532:Thiocyanic acid
13413:
13406:
13316:
13256:Ethynyl radical
13192:
13186:
13185:
13184:
13183:
13177:
13176:
13175:
13174:
13165:
13156:Sulfur monoxide
13141:Sodium chloride
13126:Silicon carbide
13033:Diatomic carbon
13023:Carbon monoxide
12965:
12960:
12930:
12925:
12903:
12861:isovaleric acid
12824:Sulfonylalkanes
12722:Hopantenic acid
12706:tolfenamic acid
12694:flufenamic acid
12656:dihydroergosine
12599:lithium bromide
12558:Others/unsorted
12553:
12414:Dichloromethane
12389:Chloral hydrate
12384:Chloral betaine
12321:
12258:
12225:
12192:
12164:
11893:Cyclopyrrolones
11878:
11784:Etiocholanolone
11699:
11656:
11617:5-Hydroxykavain
11567:
11539:
11451:
11333:
10781:Benzodiazepines
10775:
10586:Ethallobarbital
10581:Enallylpropymal
10462:
10443:Tribromoethanol
10430:-Butanol (2M2P)
10376:alcoholic drink
10338:
10335:
10327:
10297:
10292:
10261:
10253:
10208:
10163:Trichloromethyl
10158:Trifluoromethyl
10132:
10109:
10071:
10048:
9943:
9912:Phosphine oxide
9864:
9730:
9728:
9727:
9725:
9723:
9721:
9719:
9717:
9707:
9667:
9610:
9529:
9528:
9523:
9518:
9508:
9382:
9381:
9373:
9368:
9338:
9333:
9329:Petroleum jelly
9298:
9286:Phenylacetylene
9264:
9234:
9199:
9195:Isobutylbenzene
9159:
9131:
9081:
9052:
9011:
8995:
8949:
8927:
8866:
8810:
8799:
8758:
8705:
8652:
8634:
8594:
8537:
8496:
8438:
8430:
8424:
8412:
8366:
8308:
8301:
8295:
8284:
8282:
8270:
8254:
8186:
8183:(bicyclodecane)
8155:
8115:
8058:
8024:3-Methylpentane
8002:
7939:
7931:
7925:
7914:
7912:
7906:
7901:
7871:
7866:
7845:
7822:
7780:Cyclohexadiene
7776:Cyclopentadiene
7757:
7704:
7699:
7669:
7664:
7650:
7636:Cyclopentadiene
7619:
7562:
7557:
7468:
7467:
7466:
7448:
7444:
7439:
7434:
7433:
7423:
7421:
7416:. May 3, 2019.
7408:
7407:
7403:
7393:
7391:
7376:
7375:
7371:
7342:
7338:
7328:
7326:
7311:
7310:
7306:
7294:
7290:
7284:Wayback Machine
7275:
7271:
7265:Wayback Machine
7256:
7252:
7246:Wayback Machine
7237:
7233:
7225:
7221:
7182:
7178:
7146:
7142:
7108:
7104:
7073:
7069:
7024:
7020:
7003:
6999:
6990:
6986:
6950:
6946:
6937:
6935:
6931:
6900:
6894:
6890:
6881:
6879:
6866:
6865:
6861:
6851:
6849:
6836:
6835:
6831:
6822:
6803:
6799:
6798:
6791:
6781:
6779:
6766:
6765:
6761:
6751:
6749:
6736:
6735:
6728:
6718:
6716:
6703:
6702:
6698:
6692:Wayback Machine
6683:
6679:
6673:Wayback Machine
6664:
6660:
6615:
6611:
6606:Wayback Machine
6596:
6592:
6569:
6565:
6522:Huff J (2007).
6520:
6516:
6510:Wayback Machine
6496:
6492:
6445:
6441:
6433:
6429:
6384:
6377:
6322:
6318:
6312:Wayback Machine
6303:
6299:
6278:
6274:
6267:
6245:
6241:
6234:
6216:
6212:
6203:
6201:
6192:
6191:
6187:
6182:
6178:
6169:
6167:
6158:
6157:
6153:
6144:
6142:
6133:
6132:
6128:
6119:
6117:
6100:
6096:
6059:
6055:
6046:
6044:
6031:
6030:
6026:
6017:
6015:
6008:fileformat.info
6002:
6001:
5997:
5988:
5986:
5979:fileformat.info
5973:
5972:
5968:
5929:
5925:
5880:
5876:
5831:
5827:
5788:
5784:
5753:
5749:
5688:
5684:
5674:
5672:
5668:
5617:
5611:
5607:
5548:
5544:
5531:
5529:
5512:
5508:
5501:
5479:
5472:
5433:
5429:
5405:
5401:
5377:
5373:
5361:
5357:
5339:Wayback Machine
5329:
5325:
5316:
5314:
5312:Massive Science
5304:
5300:
5291:
5289:
5250:
5246:
5204:
5200:
5185:
5181:
5150:
5146:
5137:
5135:
5108:
5104:
5072:
5068:
5061:
5039:
5035:
5026:
5024:
5017:
5001:
4997:
4988:
4986:
4959:
4955:
4946:
4944:
4931:
4927:
4914:Wayback Machine
4903:Wayback Machine
4886:
4882:
4858:
4854:
4816:
4792:
4781:
4779:
4759:
4754:
4750:
4741:
4739:
4712:
4708:
4687:
4681:
4677:
4667:
4665:
4643:
4636:
4627:
4625:
4598:
4594:
4585:
4583:
4554:
4550:
4509:
4505:
4474:
4470:
4466:
4462:
4457:
4453:
4446:
4442:
4438:
4405:
4401:
4396:
4392:
4383:
4381:
4354:
4350:
4319:
4315:
4305:Wayback Machine
4291:
4287:
4272:
4270:
4241:
4237:
4214:
4210:
4205:
4201:
4192:
4190:
4148:
4144:
4119:
4112:
4105:
4078:
4074:
4059:
4055:
4045:
4043:
4034:
4033:
4029:
4012:
4011:
4007:
4000:
3996:
3981:
3972:
3966:Wayback Machine
3953:
3944:
3934:
3932:
3931:. June 24, 2005
3923:
3922:
3918:
3908:
3906:
3897:
3896:
3892:
3877:
3868:
3859:
3857:
3844:
3837:
3828:
3826:
3817:
3816:
3803:
3794:
3792:
3785:
3769:
3765:
3708:
3704:
3679:
3675:
3668:
3654:
3650:
3643:
3617:
3610:
3605:
3600:
3599:
3576:Wayback Machine
3565:
3561:
3556:
3548:telluropyrylium
3478:Medicine portal
3476:
3471:
3469:
3462:
3455:
3452:
3432:
3409:
3381:
3375:
3362:
3357:
3345:
3328:
3268:cytochrome P450
3231:. In bacteria,
3221:
3188:
3183:
3136:for benzene in
3126:
3028:
2953:
2945:
2939:
2935:
2931:
2916:
2914:Metal complexes
2908:Birch reduction
2884:
2865:
2852:sulfur trioxide
2840:
2811:using a strong
2748:ions and alkyl
2734:
2707:tetraethyl lead
2691:
2682:
2660:
2579:
2573:gives benzene.
2567:decarboxylation
2557:gives benzene.
2543:decarboxylation
2527:
2494:
2452:
2428:
2425:
2424:
2423:
2419:
2416:
2415:
2414:
2410:
2407:
2406:
2405:
2401:
2398:
2397:
2396:
2394:
2389:
2386:
2385:
2384:
2382:
2377:
2374:
2373:
2372:
2368:
2365:
2364:
2363:
2361:
2334:
2329:
2318:
2313:
2305:
2300:
2289:
2284:
2273:
2268:
2260:
2255:
2247:
2242:
2237:
2235:
2232:
2231:
2197:
2131:
2107:
2084:
2080:
2041:
2037:
2033:
2029:
2021:
2000:
1992:Main articles:
1990:
1923:
1917:
1885:
1873:paint strippers
1854:Ludwig Roselius
1850:
1829:
1784:
1781:
1732:polyunsaturated
1605:
1562:Auguste Laurent
1541:produced it by
1531:Michael Faraday
1507:
1502:
1401:
1397:
1378:
1371:
1366:
1365:
1364: ?)
1355:
1351:
1347:
1343:
1317:
1311:
1283:
1270:
1257:
1236:
1234:
1232:
1228:
1222:
1210:
1204:
1174:
1171:
1153:
1152:
1151:
1150:
1143:
1136:
1129:
1125:
1117:
1074:
1024:
1010:
974:
951:
929:-3267.6 kJ/mol
926:
923:
917:
913:
910:
909:Std enthalpy of
899:
896:
890:
886:
883:
882:Std enthalpy of
875:173.26 J/mol·K
872:
869:
862:
859:
848:
841:
821:
811:Trigonal planar
807:
805:Molecular shape
792:
790:
788:
773:1.4948 (30 °C)
772:
768:
766:
748:
734:
698:
696:
657:
655:
639:
623:
621:
593:
586:
566:
564:
562:
560:
558:
556:
555:1.81 g/L (9 °C)
554:
553:1.53 g/L (0 °C)
550:
511:sweet aromatic
490:
480:
474:
466:
452:
449:
444:
443:
432:
429:
428:
425:
419:
418:
407:
389:
382:
373:
353:
337:
324:
312:
292:
255:
235:
215:
195:
182:
171:
158:
144:
139:
137:
135:
124:
123:
107:
104:
90:
77:
58:
55:
42:
35:
28:
23:
22:
15:
12:
11:
5:
14547:
14537:
14536:
14531:
14526:
14521:
14516:
14511:
14509:Petrochemicals
14506:
14501:
14496:
14491:
14486:
14481:
14476:
14471:
14466:
14461:
14456:
14451:
14446:
14429:
14428:
14426:
14425:
14413:
14401:
14389:
14376:
14373:
14372:
14370:
14369:
14364:
14359:
14354:
14348:
14343:
14338:
14333:
14328:
14323:
14318:
14313:
14308:
14303:
14298:
14293:
14288:
14283:
14278:
14273:
14268:
14263:
14258:
14256:Cosmochemistry
14253:
14248:
14243:
14238:
14233:
14228:
14223:
14221:Astrochemistry
14218:
14213:
14207:
14205:
14199:
14198:
14196:
14195:
14190:
14185:
14180:
14175:
14171:
14167:
14162:
14158:
14153:
14148:
14143:
14138:
14133:
14127:
14125:
14119:
14118:
14116:
14115:
14110:
14105:
14101:
14096:
14091:
14086:
14081:
14076:
14074:Formyl radical
14071:
14066:
14060:
14054:
14052:
14044:
14043:
14040:
14039:
14037:
14036:
14031:
14026:
14021:
14016:
14011:
14006:
14004:Methyl acetate
14001:
13996:
13991:
13986:
13981:
13977:
13973:
13969:
13963:
13958:
13953:
13947:
13945:
13935:
13934:
13932:
13931:
13926:
13921:
13916:
13911:
13906:
13901:
13896:
13894:Dimethyl ether
13891:
13886:
13880:
13878:
13870:
13869:
13867:
13866:
13861:
13859:Methyl formate
13856:
13851:
13846:
13844:Glycolaldehyde
13841:
13836:
13831:
13826:
13820:
13818:
13810:
13809:
13807:
13806:
13801:
13796:
13791:
13786:
13781:
13779:Glycolonitrile
13776:
13774:Ethylene oxide
13771:
13766:
13765:
13764:
13754:
13748:
13746:
13738:
13737:
13735:
13734:
13729:
13724:
13719:
13714:
13709:
13704:
13699:
13694:
13690:
13685:
13680:
13675:
13673:Cyclopropenone
13670:
13665:
13660:
13654:
13652:
13644:
13643:
13641:
13640:
13635:
13630:
13625:
13620:
13615:
13610:
13605:
13600:
13595:
13590:
13585:
13580:
13575:
13573:Cyanoacetylene
13570:
13565:
13560:
13555:
13548:
13546:
13538:
13537:
13535:
13534:
13529:
13524:
13519:
13514:
13509:
13504:
13499:
13494:
13492:Methyl radical
13489:
13484:
13479:
13474:
13469:
13467:Isocyanic acid
13464:
13459:
13454:
13449:
13444:
13439:
13434:
13432:Isocyanic acid
13429:
13424:
13418:
13416:
13408:
13407:
13405:
13404:
13399:
13394:
13389:
13384:
13379:
13377:Sulfur dioxide
13374:
13369:
13364:
13359:
13354:
13352:Sodium cyanide
13349:
13344:
13339:
13334:
13329:
13324:
13319:
13314:
13310:
13305:
13300:
13295:
13290:
13285:
13280:
13275:
13269:
13263:
13261:Formyl radical
13258:
13253:
13248:
13243:
13238:
13233:
13228:
13223:
13221:Carbon dioxide
13218:
13213:
13208:
13202:
13200:
13194:
13193:
13168:
13166:
13164:
13163:
13158:
13153:
13148:
13143:
13138:
13133:
13128:
13123:
13118:
13113:
13108:
13102:
13097:
13092:
13086:
13081:
13076:
13071:
13069:Iron(II) oxide
13066:
13061:
13055:
13050:
13045:
13040:
13035:
13030:
13025:
13020:
13015:
13010:
13005:
13000:
12995:
12990:
12984:
12982:
12973:
12967:
12966:
12959:
12958:
12951:
12944:
12936:
12927:
12926:
12908:
12905:
12904:
12902:
12901:
12896:
12891:
12886:
12877:
12876:
12869:valerenic acid
12854:
12849:
12839:
12821:
12816:
12811:
12806:
12801:
12796:
12791:
12786:
12781:
12776:
12771:
12766:
12761:
12739:
12734:
12729:
12724:
12719:
12714:
12709:
12698:mefenamic acid
12687:
12682:
12677:
12672:
12667:
12645:
12640:
12635:
12630:
12625:
12620:
12615:
12610:
12607:sodium bromide
12592:
12582:
12577:
12572:
12567:
12561:
12559:
12555:
12554:
12552:
12551:
12546:
12541:
12536:
12531:
12526:
12521:
12516:
12511:
12506:
12501:
12496:
12491:
12486:
12481:
12476:
12474:Methoxypropane
12471:
12469:Methoxyflurane
12466:
12461:
12456:
12451:
12446:
12441:
12436:
12431:
12429:Ethyl chloride
12426:
12421:
12416:
12411:
12406:
12401:
12396:
12391:
12386:
12381:
12376:
12371:
12366:
12361:
12356:
12351:
12346:
12341:
12335:
12333:
12323:
12322:
12320:
12319:
12314:
12309:
12304:
12299:
12294:
12289:
12284:
12279:
12274:
12268:
12266:
12264:Quinazolinones
12260:
12259:
12257:
12256:
12251:
12246:
12241:
12235:
12233:
12227:
12226:
12224:
12223:
12218:
12213:
12208:
12202:
12200:
12194:
12193:
12191:
12190:
12185:
12180:
12174:
12172:
12166:
12165:
12163:
12162:
12157:
12152:
12147:
12142:
12137:
12132:
12127:
12122:
12117:
12112:
12107:
12102:
12097:
12092:
12087:
12082:
12077:
12072:
12067:
12062:
12057:
12052:
12047:
12042:
12037:
12032:
12027:
12022:
12017:
12007:
12006:
12001:
11996:
11991:
11986:
11981:
11976:
11971:
11959:
11958:
11953:
11948:
11943:
11938:
11926:
11925:
11920:
11915:
11910:
11905:
11900:
11888:
11886:
11880:
11879:
11877:
11876:
11871:
11866:
11861:
11856:
11851:
11846:
11841:
11836:
11831:
11826:
11821:
11816:
11811:
11806:
11801:
11796:
11791:
11786:
11781:
11776:
11771:
11766:
11761:
11756:
11751:
11745:
11740:
11735:
11730:
11725:
11720:
11715:
11709:
11707:
11701:
11700:
11698:
11697:
11692:
11687:
11682:
11677:
11672:
11666:
11664:
11658:
11657:
11655:
11654:
11649:
11644:
11639:
11634:
11629:
11624:
11619:
11614:
11609:
11604:
11599:
11594:
11589:
11584:
11578:
11576:
11569:
11568:
11566:
11565:
11560:
11555:
11549:
11547:
11541:
11540:
11538:
11537:
11532:
11522:
11517:
11512:
11507:
11502:
11497:
11492:
11487:
11482:
11477:
11472:
11467:
11461:
11459:
11453:
11452:
11450:
11449:
11444:
11439:
11434:
11429:
11424:
11419:
11414:
11409:
11404:
11399:
11394:
11389:
11384:
11379:
11374:
11369:
11364:
11359:
11354:
11349:
11343:
11341:
11335:
11334:
11332:
11331:
11326:
11321:
11316:
11311:
11306:
11301:
11296:
11291:
11286:
11281:
11276:
11271:
11266:
11261:
11256:
11251:
11246:
11241:
11236:
11231:
11226:
11221:
11216:
11211:
11206:
11201:
11196:
11191:
11186:
11181:
11176:
11171:
11166:
11161:
11156:
11151:
11146:
11141:
11136:
11131:
11126:
11121:
11116:
11111:
11106:
11101:
11096:
11091:
11086:
11081:
11076:
11071:
11066:
11061:
11056:
11051:
11046:
11041:
11036:
11031:
11026:
11021:
11016:
11011:
11006:
11001:
10996:
10991:
10986:
10981:
10976:
10971:
10966:
10961:
10956:
10951:
10946:
10941:
10936:
10931:
10926:
10921:
10916:
10911:
10906:
10901:
10896:
10891:
10886:
10881:
10876:
10871:
10866:
10861:
10856:
10851:
10846:
10841:
10836:
10831:
10826:
10821:
10816:
10811:
10806:
10801:
10796:
10791:
10785:
10783:
10777:
10776:
10774:
10773:
10768:
10763:
10758:
10753:
10748:
10743:
10738:
10733:
10728:
10723:
10718:
10713:
10708:
10703:
10698:
10693:
10688:
10686:Propylbarbital
10683:
10678:
10673:
10668:
10663:
10658:
10653:
10648:
10643:
10638:
10633:
10628:
10623:
10618:
10613:
10608:
10603:
10598:
10593:
10588:
10583:
10578:
10573:
10568:
10563:
10561:Crotylbarbital
10558:
10553:
10548:
10543:
10538:
10533:
10528:
10526:Brophebarbital
10523:
10521:Brallobarbital
10518:
10513:
10508:
10503:
10498:
10493:
10488:
10483:
10478:
10472:
10470:
10464:
10463:
10461:
10460:
10455:
10450:
10445:
10440:
10432:
10424:
10419:
10414:
10409:
10407:Methylpentynol
10404:
10399:
10394:
10389:
10384:
10379:
10369:
10364:
10359:
10354:
10348:
10346:
10340:
10339:
10333:
10326:
10325:
10318:
10311:
10303:
10294:
10293:
10291:
10290:
10289:
10288:
10283:
10271:
10264:
10258:
10255:
10254:
10252:
10251:
10249:Sulfinylamines
10246:
10241:
10236:
10231:
10229:Phosphoramides
10226:
10224:Isothiocyanate
10220:
10218:
10214:
10213:
10210:
10209:
10207:
10206:
10201:
10200:
10199:
10189:
10188:
10187:
10177:
10176:
10175:
10170:
10165:
10160:
10155:
10144:
10142:
10134:
10133:
10131:
10130:
10125:
10119:
10117:
10111:
10110:
10108:
10107:
10102:
10100:Selenenic acid
10097:
10095:Seleninic acid
10092:
10090:Selenonic acid
10087:
10081:
10079:
10073:
10072:
10070:
10069:
10064:
10058:
10056:
10050:
10049:
10047:
10046:
10041:
10036:
10031:
10026:
10021:
10016:
10011:
10006:
10001:
9996:
9991:
9986:
9981:
9976:
9971:
9970:
9969:
9959:
9953:
9951:
9945:
9944:
9942:
9941:
9936:
9931:
9926:
9925:
9924:
9914:
9909:
9904:
9899:
9898:
9897:
9887:
9886:
9885:
9883:Phosphodiester
9874:
9872:
9866:
9865:
9863:
9862:
9857:
9852:
9847:
9842:
9837:
9832:
9827:
9822:
9817:
9812:
9807:
9802:
9797:
9792:
9787:
9782:
9777:
9772:
9767:
9762:
9761:
9760:
9755:
9744:
9742:
9733:
9729:(one element,
9713:
9712:
9709:
9708:
9706:
9705:
9704:
9703:
9693:
9692:
9691:
9686:
9675:
9673:
9669:
9668:
9666:
9665:
9660:
9655:
9654:
9653:
9643:
9642:
9641:
9636:
9631:
9620:
9618:
9612:
9611:
9609:
9608:
9606:Methylenedioxy
9603:
9598:
9597:
9596:
9591:
9581:
9580:
9579:
9574:
9564:
9563:
9562:
9552:
9547:
9541:
9539:
9532:
9510:
9509:
9507:
9506:
9501:
9496:
9495:
9494:
9489:
9479:
9478:
9477:
9472:
9467:
9462:
9457:
9452:
9442:
9441:
9440:
9435:
9425:
9424:
9423:
9418:
9413:
9408:
9403:
9398:
9387:
9385:
9383:(only C and H)
9375:
9374:
9367:
9366:
9359:
9352:
9344:
9335:
9334:
9332:
9331:
9326:
9321:
9316:
9310:
9308:
9304:
9303:
9300:
9299:
9297:
9296:
9288:
9283:
9278:
9272:
9270:
9266:
9265:
9263:
9262:
9260:4-Vinyltoluene
9257:
9255:Divinylbenzene
9252:
9246:
9244:
9240:
9239:
9236:
9235:
9233:
9232:
9227:
9222:
9220:2-Phenylhexane
9217:
9211:
9209:
9205:
9204:
9201:
9200:
9198:
9197:
9192:
9184:
9176:
9167:
9165:
9161:
9160:
9158:
9157:
9152:
9147:
9141:
9139:
9133:
9132:
9130:
9129:
9121:
9113:
9104:
9102:
9093:
9087:
9086:
9083:
9082:
9080:
9079:
9077:4-Ethyltoluene
9074:
9072:-Propylbenzene
9066:
9060:
9058:
9054:
9053:
9051:
9050:
9045:
9040:
9034:
9032:
9023:
9017:
9016:
9013:
9012:
9010:
9009:
9003:
9001:
8997:
8996:
8994:
8993:
8985:
8977:
8968:
8966:
8957:
8948:
8947:
8941:
8939:
8933:
8932:
8929:
8928:
8926:
8925:
8920:
8915:
8910:
8905:
8900:
8895:
8890:
8885:
8880:
8874:
8872:
8868:
8867:
8865:
8864:
8859:
8854:
8849:
8844:
8839:
8833:
8831:
8822:
8813:
8805:
8804:
8801:
8800:
8798:
8797:
8792:
8787:
8782:
8777:
8772:
8766:
8764:
8760:
8759:
8757:
8756:
8751:
8746:
8741:
8736:
8731:
8726:
8721:
8715:
8713:
8707:
8706:
8704:
8703:
8698:
8693:
8688:
8683:
8678:
8673:
8668:
8662:
8660:
8654:
8653:
8651:
8650:
8644:
8642:
8640:Bicycloalkenes
8636:
8635:
8633:
8632:
8630:
8625:
8620:
8615:
8610:
8604:
8602:
8596:
8595:
8593:
8592:
8587:
8582:
8577:
8572:
8567:
8562:
8557:
8551:
8549:
8543:
8542:
8539:
8538:
8536:
8535:
8530:
8525:
8520:
8515:
8510:
8504:
8502:
8498:
8497:
8495:
8494:
8489:
8484:
8479:
8474:
8469:
8464:
8459:
8454:
8448:
8446:
8445:Linear alkynes
8439:
8432:
8426:
8418:
8417:
8414:
8413:
8411:
8410:
8405:
8400:
8395:
8390:
8385:
8380:
8374:
8372:
8368:
8367:
8365:
8364:
8359:
8354:
8349:
8344:
8339:
8334:
8329:
8324:
8318:
8316:
8315:Linear alkenes
8309:
8303:
8297:
8286:
8276:
8275:
8272:
8271:
8269:
8268:
8262:
8260:
8256:
8255:
8253:
8252:
8247:
8242:
8237:
8232:
8227:
8222:
8217:
8212:
8207:
8202:
8196:
8194:
8188:
8187:
8185:
8184:
8178:
8172:
8165:
8163:
8161:Bicycloalkanes
8157:
8156:
8154:
8153:
8151:
8146:
8141:
8136:
8131:
8125:
8123:
8117:
8116:
8114:
8113:
8108:
8103:
8098:
8093:
8088:
8083:
8078:
8072:
8070:
8064:
8063:
8060:
8059:
8057:
8056:
8051:
8046:
8041:
8036:
8031:
8026:
8021:
8016:
8010:
8008:
8004:
8003:
8001:
8000:
7995:
7990:
7985:
7980:
7975:
7970:
7965:
7960:
7955:
7949:
7947:
7946:Linear alkanes
7940:
7933:
7927:
7916:
7908:
7907:
7900:
7899:
7892:
7885:
7877:
7868:
7867:
7865:
7864:
7859:
7853:
7851:
7847:
7846:
7844:
7843:
7838:
7832:
7830:
7824:
7823:
7821:
7820:
7819:
7818:
7811:Cyclooctadiene
7808:
7807:
7806:
7801:
7793:
7792:
7791:
7786:
7778:
7773:
7771:Cyclobutadiene
7767:
7765:
7759:
7758:
7756:
7755:
7750:
7745:
7740:
7735:
7730:
7725:
7720:
7714:
7712:
7706:
7705:
7698:
7697:
7690:
7683:
7675:
7666:
7665:
7655:
7652:
7651:
7649:
7648:
7643:
7638:
7633:
7627:
7625:
7621:
7620:
7618:
7617:
7610:
7605:
7598:
7593:
7588:
7583:
7576:
7574:Cyclobutadiene
7570:
7568:
7564:
7563:
7556:
7555:
7548:
7541:
7533:
7527:
7526:
7521:
7516:
7510:
7505:
7496:
7491:
7486:
7481:
7449:
7442:
7441:
7440:
7438:
7437:External links
7435:
7432:
7431:
7401:
7369:
7356:(2): 274–284.
7336:
7304:
7288:
7269:
7250:
7231:
7219:
7176:
7140:
7102:
7067:
7018:
6997:
6991:ACGIH (2009).
6984:
6944:
6888:
6859:
6829:
6789:
6759:
6726:
6696:
6677:
6658:
6609:
6590:
6573:J Environ Biol
6563:
6514:
6490:
6459:(1): 133–148.
6439:
6427:
6375:
6316:
6297:
6272:
6265:
6239:
6232:
6210:
6185:
6176:
6151:
6126:
6094:
6053:
6024:
5995:
5966:
5923:
5874:
5825:
5782:
5763:(29): 9342–3.
5747:
5682:
5605:
5542:
5506:
5500:978-3527306732
5499:
5470:
5443:(8): 547–561.
5427:
5413:2015-10-23 at
5399:
5385:2015-11-28 at
5378:Graebe (1869)
5371:
5355:
5345:, 2nd series,
5323:
5298:
5244:
5198:
5179:
5144:
5102:
5066:
5059:
5033:
5016:978-0226723358
5015:
4995:
4953:
4925:
4880:
4852:
4850:
4849:
4812:
4811:
4788:
4787:
4748:
4706:
4675:
4634:
4592:
4548:
4519:in Breisgau),
4503:
4498:10.1086/318871
4472:
4468:
4464:
4460:
4451:
4444:
4440:
4436:
4399:
4390:
4368:(2): 162–180.
4348:
4313:
4285:
4235:
4224:(5): 345–350.
4208:
4203:
4199:
4142:
4110:
4104:978-0684181950
4103:
4072:
4053:
4027:
4005:
3994:
3970:
3942:
3916:
3890:
3866:
3835:
3801:
3783:
3763:
3702:
3691:(2): 253–256.
3673:
3666:
3648:
3641:
3607:
3606:
3604:
3601:
3598:
3597:
3558:
3557:
3555:
3552:
3551:
3550:
3544:selenopyrylium
3500:
3493:
3488:
3482:
3481:
3467:
3451:
3448:
3431:
3428:
3408:
3405:
3397:United Kingdom
3377:Main article:
3374:
3371:
3361:
3358:
3356:
3353:
3344:
3341:
3327:
3324:
3243:) to a cyclic
3220:
3217:
3187:
3184:
3182:
3179:
3142:leukemogenesis
3138:drinking water
3125:
3122:
3027:
3024:
2952:
2951:Health effects
2949:
2943:
2937:
2933:
2929:
2924:organometallic
2915:
2912:
2883:
2880:
2863:
2839:
2836:
2785:
2784:
2783:
2782:
2765:
2764:
2733:
2730:
2690:
2687:
2578:
2575:
2526:
2523:
2497:Steam cracking
2493:
2492:Steam cracking
2490:
2451:
2448:
2433:
2432:
2426:
2417:
2408:
2399:
2387:
2375:
2366:
2350:
2349:
2332:
2324:
2316:
2303:
2295:
2287:
2279:
2271:
2258:
2245:
2196:
2193:
2130:
2127:
2119:steam cracking
2106:
2103:
2082:
2078:
2039:
2035:
2031:
2027:
2019:
1989:
1986:
1946:delocalization
1940:(pm). The C–C
1919:Main article:
1916:
1913:
1884:
1881:
1877:rubber cements
1849:
1846:
1833:Wilhelm Körner
1828:
1825:
1786:
1785:
1782:
1775:
1765:monoderivative
1738:atom for each
1722:
1721:
1714:
1707:
1699:
1698:
1691:
1684:
1676:
1675:
1667:
1666:
1658:
1657:
1650:
1643:
1635:
1634:
1627:
1620:
1612:
1611:
1604:
1601:
1572:benzene, and "
1506:
1503:
1501:
1498:
1435:petrochemicals
1402:. The benzene
1399:
1395:
1376:
1373:
1372:
1367:
1345:
1344:
1340:standard state
1337:
1334:
1333:
1327:
1326:
1322:
1321:
1312:
1309:
1306:
1305:
1301:
1300:
1295:
1288:
1287:
1284:
1278:
1275:
1274:
1271:
1265:
1262:
1261:
1258:
1252:
1249:
1248:
1239:
1238:
1229:
1220:
1218:
1215:
1214:
1211:
1202:
1200:
1197:
1196:
1189:
1188:
1185:
1179:
1178:
1175:
1168:
1165:
1164:
1161:
1155:
1154:
1144:
1137:
1130:
1115:
1114:
1113:
1112:
1110:
1101:
1100:
1090:P305+P351+P338
1075:
1070:
1067:
1066:
1025:
1020:
1017:
1016:
1011:
1006:
1003:
1002:
975:
970:
967:
966:
956:
955:
952:
949:
946:
945:
936:
935:
931:
930:
927:
921:
915:
907:
904:
903:
900:
894:
888:
880:
877:
876:
873:
867:
856:
853:
852:
851:134.8 J/mol·K
849:
837:
834:
833:
829:
828:
822:
817:
814:
813:
808:
803:
800:
799:
795:
794:
781:
775:
774:
771:1.5011 (20 °C)
769:
764:
756:
753:
752:
749:
743:
740:
739:
736:
732:
725:
724:
719:
717:Conjugate base
713:
712:
707:
705:Conjugate acid
701:
700:
693:
691:Vapor pressure
687:
686:
683:
674:
673:
670:
660:
659:
652:
642:
641:
636:
626:
625:
618:
608:
607:
591:
584:
575:
569:
568:
551:
546:
543:
542:
539:
533:
532:
529:
523:
522:
519:
513:
512:
509:
503:
502:
499:
495:
494:
488:
482:
481:
478:
472:
467:
462:
459:
458:
454:
453:
451:
450:
447:
439:
438:
437:
434:
433:
431:
430:
426:
423:
422:
414:
413:
412:
409:
408:
406:
405:
392:
390:
378:
375:
374:
372:
371:
363:
361:
355:
354:
352:
351:
347:
345:
339:
338:
336:
335:
327:
325:
317:
314:
313:
311:
310:
302:
300:
294:
293:
291:
290:
286:
284:
276:
275:
265:
257:
256:
254:
253:
245:
243:
237:
236:
234:
233:
225:
223:
217:
216:
214:
213:
205:
203:
197:
196:
194:
193:
185:
183:
176:
173:
172:
170:
169:
161:
159:
154:
151:
150:
146:
145:
130:
126:
125:
121:
120:
114:
113:
109:
108:
105:
96:
95:
92:
91:
88:
78:
75:
60:
59:
56:
26:
9:
6:
4:
3:
2:
14546:
14535:
14532:
14530:
14527:
14525:
14522:
14520:
14517:
14515:
14512:
14510:
14507:
14505:
14502:
14500:
14497:
14495:
14492:
14490:
14487:
14485:
14482:
14480:
14477:
14475:
14472:
14470:
14467:
14465:
14462:
14460:
14457:
14455:
14452:
14450:
14447:
14445:
14442:
14441:
14439:
14424:
14414:
14412:
14402:
14400:
14390:
14388:
14387:
14378:
14377:
14374:
14368:
14365:
14363:
14360:
14358:
14355:
14352:
14349:
14347:
14344:
14342:
14339:
14337:
14334:
14332:
14329:
14327:
14324:
14322:
14319:
14317:
14314:
14312:
14309:
14307:
14304:
14302:
14299:
14297:
14294:
14292:
14289:
14287:
14286:Homochirality
14284:
14282:
14279:
14277:
14274:
14272:
14269:
14267:
14264:
14262:
14259:
14257:
14254:
14252:
14249:
14247:
14244:
14242:
14239:
14237:
14234:
14232:
14229:
14227:
14224:
14222:
14219:
14217:
14214:
14212:
14209:
14208:
14206:
14204:
14200:
14194:
14191:
14189:
14186:
14184:
14181:
14179:
14176:
14174:
14168:
14166:
14159:
14157:
14154:
14152:
14149:
14147:
14144:
14142:
14141:Methoxyethane
14139:
14137:
14134:
14132:
14129:
14128:
14126:
14124:
14120:
14114:
14111:
14109:
14102:
14100:
14097:
14095:
14092:
14090:
14087:
14085:
14082:
14080:
14077:
14075:
14072:
14070:
14067:
14064:
14061:
14059:
14056:
14055:
14053:
14049:
14045:
14035:
14032:
14030:
14027:
14025:
14024:Butyronitrile
14022:
14020:
14017:
14015:
14012:
14010:
14007:
14005:
14002:
14000:
13999:Ethyl formate
13997:
13995:
13992:
13990:
13987:
13985:
13978:
13967:
13964:
13962:
13959:
13957:
13954:
13952:
13949:
13948:
13946:
13944:
13936:
13930:
13927:
13925:
13924:Propionitrile
13922:
13920:
13917:
13915:
13912:
13910:
13907:
13905:
13902:
13900:
13897:
13895:
13892:
13890:
13887:
13885:
13882:
13881:
13879:
13877:
13871:
13865:
13862:
13860:
13857:
13855:
13852:
13850:
13847:
13845:
13842:
13840:
13837:
13835:
13832:
13830:
13827:
13825:
13822:
13821:
13819:
13817:
13811:
13805:
13804:Vinyl alcohol
13802:
13800:
13797:
13795:
13792:
13790:
13787:
13785:
13782:
13780:
13777:
13775:
13772:
13770:
13767:
13763:
13762:Vinyl cyanide
13760:
13759:
13758:
13757:Acrylonitrile
13755:
13753:
13750:
13749:
13747:
13745:
13739:
13733:
13730:
13728:
13725:
13723:
13722:Pentynylidyne
13720:
13718:
13715:
13713:
13710:
13708:
13705:
13703:
13700:
13698:
13691:
13689:
13686:
13684:
13681:
13679:
13676:
13674:
13671:
13669:
13666:
13664:
13661:
13659:
13656:
13655:
13653:
13651:
13645:
13639:
13636:
13634:
13631:
13629:
13626:
13624:
13621:
13619:
13618:Methylenimine
13616:
13614:
13611:
13609:
13606:
13604:
13601:
13599:
13596:
13594:
13591:
13589:
13586:
13584:
13581:
13579:
13576:
13574:
13571:
13569:
13566:
13564:
13561:
13559:
13556:
13553:
13550:
13549:
13547:
13545:
13539:
13533:
13530:
13528:
13525:
13523:
13520:
13518:
13515:
13513:
13510:
13508:
13505:
13503:
13500:
13498:
13497:Propynylidyne
13495:
13493:
13490:
13488:
13487:Methyl cation
13485:
13483:
13480:
13478:
13475:
13473:
13470:
13468:
13465:
13463:
13460:
13458:
13455:
13453:
13450:
13448:
13447:Fulminic acid
13445:
13443:
13440:
13438:
13435:
13433:
13430:
13428:
13425:
13423:
13420:
13419:
13417:
13415:
13409:
13403:
13400:
13398:
13395:
13393:
13390:
13388:
13385:
13383:
13380:
13378:
13375:
13373:
13370:
13368:
13365:
13363:
13360:
13358:
13355:
13353:
13350:
13348:
13345:
13343:
13340:
13338:
13335:
13333:
13330:
13328:
13325:
13323:
13322:Nitrous oxide
13320:
13318:
13311:
13309:
13306:
13304:
13301:
13299:
13296:
13294:
13291:
13289:
13286:
13284:
13281:
13279:
13276:
13273:
13270:
13267:
13264:
13262:
13259:
13257:
13254:
13252:
13249:
13247:
13244:
13242:
13239:
13237:
13234:
13232:
13229:
13227:
13224:
13222:
13219:
13217:
13216:Amino radical
13214:
13212:
13209:
13207:
13204:
13203:
13201:
13199:
13195:
13190:
13181:
13172:
13162:
13159:
13157:
13154:
13152:
13149:
13147:
13146:Sodium iodide
13144:
13142:
13139:
13137:
13134:
13132:
13129:
13127:
13124:
13122:
13119:
13117:
13114:
13112:
13109:
13106:
13103:
13101:
13098:
13096:
13093:
13090:
13087:
13085:
13082:
13080:
13077:
13075:
13072:
13070:
13067:
13065:
13062:
13059:
13056:
13054:
13051:
13049:
13046:
13044:
13041:
13039:
13036:
13034:
13031:
13029:
13028:Cyano radical
13026:
13024:
13021:
13019:
13016:
13014:
13011:
13009:
13008:Carbon cation
13006:
13004:
13001:
12999:
12996:
12994:
12991:
12989:
12986:
12985:
12983:
12981:
12977:
12974:
12972:
12968:
12964:
12957:
12952:
12950:
12945:
12943:
12938:
12937:
12934:
12924:
12923:
12919:
12915:
12912:
12906:
12900:
12897:
12895:
12892:
12890:
12887:
12885:
12882:
12879:
12878:
12874:
12870:
12866:
12865:isovaleramide
12862:
12858:
12855:
12853:
12850:
12847:
12843:
12840:
12837:
12833:
12829:
12825:
12822:
12820:
12817:
12815:
12812:
12810:
12807:
12805:
12802:
12800:
12797:
12795:
12792:
12790:
12787:
12785:
12782:
12780:
12777:
12775:
12772:
12770:
12767:
12765:
12762:
12759:
12755:
12751:
12747:
12743:
12740:
12738:
12735:
12733:
12730:
12728:
12725:
12723:
12720:
12718:
12715:
12713:
12710:
12707:
12703:
12702:niflumic acid
12699:
12695:
12691:
12688:
12686:
12683:
12681:
12678:
12676:
12673:
12671:
12668:
12665:
12661:
12657:
12653:
12649:
12646:
12644:
12641:
12639:
12636:
12634:
12631:
12629:
12628:Clomethiazole
12626:
12624:
12623:Chlormezanone
12621:
12619:
12616:
12614:
12613:Carbamazepine
12611:
12608:
12604:
12600:
12596:
12593:
12590:
12586:
12583:
12581:
12578:
12576:
12573:
12571:
12568:
12566:
12563:
12562:
12560:
12556:
12550:
12547:
12545:
12542:
12540:
12537:
12535:
12532:
12530:
12527:
12525:
12522:
12520:
12517:
12515:
12512:
12510:
12507:
12505:
12502:
12500:
12497:
12495:
12492:
12490:
12489:Nitrous oxide
12487:
12485:
12482:
12480:
12477:
12475:
12472:
12470:
12467:
12465:
12462:
12460:
12457:
12455:
12452:
12450:
12447:
12445:
12442:
12440:
12437:
12435:
12432:
12430:
12427:
12425:
12422:
12420:
12419:Diethyl ether
12417:
12415:
12412:
12410:
12407:
12405:
12402:
12400:
12397:
12395:
12392:
12390:
12387:
12385:
12382:
12380:
12377:
12375:
12372:
12370:
12367:
12365:
12362:
12360:
12357:
12355:
12352:
12350:
12347:
12345:
12342:
12340:
12337:
12336:
12334:
12332:
12328:
12324:
12318:
12315:
12313:
12310:
12308:
12305:
12303:
12300:
12298:
12295:
12293:
12290:
12288:
12285:
12283:
12280:
12278:
12275:
12273:
12270:
12269:
12267:
12265:
12261:
12255:
12252:
12250:
12247:
12245:
12242:
12240:
12237:
12236:
12234:
12232:
12228:
12222:
12221:Pyrithyldione
12219:
12217:
12214:
12212:
12209:
12207:
12204:
12203:
12201:
12199:
12195:
12189:
12186:
12184:
12181:
12179:
12176:
12175:
12173:
12171:
12167:
12161:
12158:
12156:
12153:
12151:
12148:
12146:
12143:
12141:
12138:
12136:
12133:
12131:
12128:
12126:
12123:
12121:
12118:
12116:
12113:
12111:
12108:
12106:
12103:
12101:
12098:
12096:
12093:
12091:
12088:
12086:
12083:
12081:
12078:
12076:
12073:
12071:
12068:
12066:
12063:
12061:
12058:
12056:
12053:
12051:
12048:
12046:
12043:
12041:
12038:
12036:
12033:
12031:
12028:
12026:
12023:
12021:
12018:
12016:
12012:
12009:
12008:
12005:
12002:
12000:
11997:
11995:
11992:
11990:
11987:
11985:
11982:
11980:
11977:
11975:
11972:
11970:
11966:
11965:
11961:
11960:
11957:
11954:
11952:
11949:
11947:
11944:
11942:
11939:
11937:
11933:
11932:
11928:
11927:
11924:
11921:
11919:
11916:
11914:
11911:
11909:
11906:
11904:
11901:
11899:
11895:
11894:
11890:
11889:
11887:
11885:
11881:
11875:
11872:
11870:
11867:
11865:
11862:
11860:
11857:
11855:
11852:
11850:
11847:
11845:
11842:
11840:
11837:
11835:
11832:
11830:
11827:
11825:
11822:
11820:
11817:
11815:
11812:
11810:
11807:
11805:
11802:
11800:
11797:
11795:
11792:
11790:
11787:
11785:
11782:
11780:
11777:
11775:
11772:
11770:
11767:
11765:
11762:
11760:
11757:
11755:
11752:
11750:
11746:
11744:
11741:
11739:
11736:
11734:
11731:
11729:
11726:
11724:
11721:
11719:
11716:
11714:
11711:
11710:
11708:
11706:
11702:
11696:
11693:
11691:
11688:
11686:
11683:
11681:
11678:
11676:
11673:
11671:
11668:
11667:
11665:
11663:
11659:
11653:
11650:
11648:
11645:
11643:
11640:
11638:
11635:
11633:
11630:
11628:
11625:
11623:
11620:
11618:
11615:
11613:
11610:
11608:
11605:
11603:
11600:
11598:
11595:
11593:
11590:
11588:
11585:
11583:
11580:
11579:
11577:
11574:
11570:
11564:
11561:
11559:
11556:
11554:
11551:
11550:
11548:
11546:
11542:
11536:
11533:
11530:
11526:
11523:
11521:
11518:
11516:
11513:
11511:
11508:
11506:
11503:
11501:
11498:
11496:
11493:
11491:
11488:
11486:
11483:
11481:
11478:
11476:
11473:
11471:
11468:
11466:
11463:
11462:
11460:
11458:
11454:
11448:
11445:
11443:
11440:
11438:
11435:
11433:
11430:
11428:
11427:Phenprobamate
11425:
11423:
11420:
11418:
11415:
11413:
11410:
11408:
11405:
11403:
11400:
11398:
11395:
11393:
11392:Hexapropymate
11390:
11388:
11385:
11383:
11380:
11378:
11375:
11373:
11370:
11368:
11367:Difebarbamate
11365:
11363:
11360:
11358:
11355:
11353:
11350:
11348:
11345:
11344:
11342:
11340:
11336:
11330:
11327:
11325:
11322:
11320:
11317:
11315:
11312:
11310:
11307:
11305:
11302:
11300:
11297:
11295:
11292:
11290:
11287:
11285:
11282:
11280:
11277:
11275:
11272:
11270:
11267:
11265:
11262:
11260:
11257:
11255:
11252:
11250:
11247:
11245:
11242:
11240:
11237:
11235:
11232:
11230:
11227:
11225:
11222:
11220:
11217:
11215:
11212:
11210:
11207:
11205:
11202:
11200:
11197:
11195:
11192:
11190:
11187:
11185:
11182:
11180:
11179:Nortetrazepam
11177:
11175:
11172:
11170:
11167:
11165:
11162:
11160:
11157:
11155:
11152:
11150:
11147:
11145:
11142:
11140:
11137:
11135:
11132:
11130:
11127:
11125:
11122:
11120:
11117:
11115:
11112:
11110:
11107:
11105:
11102:
11100:
11097:
11095:
11092:
11090:
11087:
11085:
11082:
11080:
11077:
11075:
11072:
11070:
11067:
11065:
11062:
11060:
11057:
11055:
11052:
11050:
11047:
11045:
11042:
11040:
11039:Flutoprazepam
11037:
11035:
11032:
11030:
11027:
11025:
11022:
11020:
11019:Flunitrazolam
11017:
11015:
11014:Flunitrazepam
11012:
11010:
11007:
11005:
11004:Flubromazolam
11002:
11000:
10999:Flubromazepam
10997:
10995:
10992:
10990:
10987:
10985:
10982:
10980:
10977:
10975:
10972:
10970:
10967:
10965:
10962:
10960:
10957:
10955:
10952:
10950:
10947:
10945:
10942:
10940:
10937:
10935:
10932:
10930:
10927:
10925:
10922:
10920:
10917:
10915:
10912:
10910:
10907:
10905:
10902:
10900:
10899:Cloniprazepam
10897:
10895:
10892:
10890:
10887:
10885:
10882:
10880:
10877:
10875:
10872:
10870:
10867:
10865:
10862:
10860:
10857:
10855:
10852:
10850:
10847:
10845:
10842:
10840:
10837:
10835:
10832:
10830:
10827:
10825:
10822:
10820:
10817:
10815:
10812:
10810:
10807:
10805:
10802:
10800:
10797:
10795:
10792:
10790:
10789:2-Oxoquazepam
10787:
10786:
10784:
10782:
10778:
10772:
10769:
10767:
10764:
10762:
10759:
10757:
10754:
10752:
10749:
10747:
10744:
10742:
10739:
10737:
10734:
10732:
10731:Thialbarbital
10729:
10727:
10726:Tetrabarbital
10724:
10722:
10719:
10717:
10714:
10712:
10711:Spirobarbital
10709:
10707:
10704:
10702:
10699:
10697:
10694:
10692:
10691:Proxibarbital
10689:
10687:
10684:
10682:
10681:Propallylonal
10679:
10677:
10674:
10672:
10669:
10667:
10664:
10662:
10661:Phenobarbital
10659:
10657:
10654:
10652:
10651:Pentobarbital
10649:
10647:
10644:
10642:
10641:Narcobarbital
10639:
10637:
10634:
10632:
10629:
10627:
10624:
10622:
10619:
10617:
10614:
10612:
10609:
10607:
10606:Heptobarbital
10604:
10602:
10599:
10597:
10594:
10592:
10589:
10587:
10584:
10582:
10579:
10577:
10576:Difebarbamate
10574:
10572:
10569:
10567:
10566:Cyclobarbital
10564:
10562:
10559:
10557:
10554:
10552:
10549:
10547:
10544:
10542:
10539:
10537:
10534:
10532:
10529:
10527:
10524:
10522:
10519:
10517:
10514:
10512:
10511:Benzobarbital
10509:
10507:
10504:
10502:
10499:
10497:
10494:
10492:
10489:
10487:
10484:
10482:
10479:
10477:
10474:
10473:
10471:
10469:
10465:
10459:
10456:
10454:
10451:
10449:
10446:
10444:
10441:
10439:
10437:
10433:
10431:
10429:
10425:
10423:
10420:
10418:
10415:
10413:
10410:
10408:
10405:
10403:
10400:
10398:
10395:
10393:
10390:
10388:
10385:
10383:
10382:Ethchlorvynol
10380:
10377:
10373:
10370:
10368:
10365:
10363:
10360:
10358:
10355:
10353:
10350:
10349:
10347:
10345:
10341:
10337:
10324:
10319:
10317:
10312:
10310:
10305:
10304:
10301:
10287:
10284:
10282:
10279:
10278:
10277:
10276:
10272:
10270:
10269:
10265:
10260:
10259:
10256:
10250:
10247:
10245:
10242:
10240:
10237:
10235:
10232:
10230:
10227:
10225:
10222:
10221:
10219:
10215:
10205:
10202:
10198:
10195:
10194:
10193:
10190:
10186:
10183:
10182:
10181:
10178:
10174:
10171:
10169:
10166:
10164:
10161:
10159:
10156:
10154:
10151:
10150:
10149:
10146:
10145:
10143:
10141:
10140:
10135:
10129:
10128:Telluroketone
10126:
10124:
10121:
10120:
10118:
10116:
10112:
10106:
10103:
10101:
10098:
10096:
10093:
10091:
10088:
10086:
10083:
10082:
10080:
10078:
10074:
10068:
10065:
10063:
10060:
10059:
10057:
10055:
10051:
10045:
10042:
10040:
10037:
10035:
10032:
10030:
10027:
10025:
10022:
10020:
10017:
10015:
10014:Sulfonic acid
10012:
10010:
10007:
10005:
10004:Sulfinic acid
10002:
10000:
9999:Thiosulfonate
9997:
9995:
9992:
9990:
9989:Thiosulfinate
9987:
9985:
9984:Sulfenic acid
9982:
9980:
9977:
9975:
9972:
9968:
9965:
9964:
9963:
9960:
9958:
9955:
9954:
9952:
9950:
9946:
9940:
9939:Phosphaallene
9937:
9935:
9934:Phosphaalkyne
9932:
9930:
9929:Phosphaalkene
9927:
9923:
9920:
9919:
9918:
9915:
9913:
9910:
9908:
9905:
9903:
9900:
9896:
9893:
9892:
9891:
9888:
9884:
9881:
9880:
9879:
9876:
9875:
9873:
9871:
9867:
9861:
9858:
9856:
9853:
9851:
9848:
9846:
9843:
9841:
9838:
9836:
9833:
9831:
9828:
9826:
9823:
9821:
9818:
9816:
9813:
9811:
9808:
9806:
9803:
9801:
9798:
9796:
9793:
9791:
9788:
9786:
9783:
9781:
9778:
9776:
9773:
9771:
9768:
9766:
9763:
9759:
9756:
9754:
9751:
9750:
9749:
9746:
9745:
9743:
9741:
9737:
9734:
9714:
9702:
9699:
9698:
9697:
9694:
9690:
9687:
9685:
9682:
9681:
9680:
9677:
9676:
9674:
9670:
9664:
9661:
9659:
9656:
9652:
9649:
9648:
9647:
9644:
9640:
9637:
9635:
9632:
9630:
9627:
9626:
9625:
9622:
9621:
9619:
9617:
9613:
9607:
9604:
9602:
9601:Ethylenedioxy
9599:
9595:
9592:
9590:
9587:
9586:
9585:
9582:
9578:
9575:
9573:
9570:
9569:
9568:
9565:
9561:
9558:
9557:
9556:
9553:
9551:
9548:
9546:
9543:
9542:
9540:
9536:
9533:
9527:
9521:
9516:
9511:
9505:
9502:
9500:
9497:
9493:
9490:
9488:
9485:
9484:
9483:
9480:
9476:
9473:
9471:
9468:
9466:
9463:
9461:
9458:
9456:
9453:
9451:
9448:
9447:
9446:
9443:
9439:
9436:
9434:
9431:
9430:
9429:
9426:
9422:
9419:
9417:
9414:
9412:
9409:
9407:
9404:
9402:
9399:
9397:
9394:
9393:
9392:
9389:
9388:
9386:
9380:
9376:
9372:
9365:
9360:
9358:
9353:
9351:
9346:
9345:
9342:
9330:
9327:
9325:
9322:
9320:
9317:
9315:
9312:
9311:
9309:
9305:
9295:
9293:
9289:
9287:
9284:
9282:
9279:
9277:
9274:
9273:
9271:
9267:
9261:
9258:
9256:
9253:
9251:
9248:
9247:
9245:
9243:Vinylbenzenes
9241:
9231:
9228:
9226:
9223:
9221:
9218:
9216:
9213:
9212:
9210:
9206:
9196:
9193:
9191:
9190:-Butylbenzene
9189:
9185:
9183:
9182:-Butylbenzene
9181:
9177:
9175:
9174:-Butylbenzene
9173:
9169:
9168:
9166:
9162:
9156:
9153:
9151:
9148:
9146:
9143:
9142:
9140:
9138:
9134:
9128:
9126:
9122:
9120:
9118:
9114:
9112:
9110:
9106:
9105:
9103:
9101:
9097:
9094:
9092:
9088:
9078:
9075:
9073:
9071:
9067:
9065:
9062:
9061:
9059:
9055:
9049:
9046:
9044:
9041:
9039:
9036:
9035:
9033:
9031:
9027:
9024:
9022:
9018:
9008:
9005:
9004:
9002:
8998:
8992:
8990:
8986:
8984:
8982:
8978:
8976:
8974:
8970:
8969:
8967:
8965:
8961:
8958:
8956:
8952:
8946:
8943:
8942:
8940:
8938:
8937:Alkylbenzenes
8934:
8924:
8921:
8919:
8916:
8914:
8911:
8909:
8906:
8904:
8901:
8899:
8896:
8894:
8891:
8889:
8886:
8884:
8881:
8879:
8876:
8875:
8873:
8869:
8863:
8860:
8858:
8855:
8853:
8850:
8848:
8845:
8843:
8840:
8838:
8835:
8834:
8832:
8830:
8826:
8823:
8821:
8817:
8814:
8812:
8806:
8796:
8793:
8791:
8788:
8786:
8783:
8781:
8778:
8776:
8773:
8771:
8768:
8767:
8765:
8761:
8755:
8752:
8750:
8747:
8745:
8742:
8740:
8737:
8735:
8732:
8730:
8727:
8725:
8722:
8720:
8717:
8716:
8714:
8712:
8708:
8702:
8699:
8697:
8694:
8692:
8689:
8687:
8684:
8682:
8679:
8677:
8674:
8672:
8669:
8667:
8664:
8663:
8661:
8659:
8655:
8649:
8646:
8645:
8643:
8641:
8637:
8631:
8629:
8626:
8624:
8621:
8619:
8616:
8614:
8611:
8609:
8606:
8605:
8603:
8601:
8597:
8591:
8588:
8586:
8583:
8581:
8578:
8576:
8573:
8571:
8568:
8566:
8563:
8561:
8558:
8556:
8553:
8552:
8550:
8548:
8544:
8534:
8531:
8529:
8526:
8524:
8521:
8519:
8516:
8514:
8511:
8509:
8506:
8505:
8503:
8499:
8493:
8490:
8488:
8485:
8483:
8480:
8478:
8475:
8473:
8470:
8468:
8465:
8463:
8460:
8458:
8455:
8453:
8450:
8449:
8447:
8443:
8440:
8436:
8429:
8423:
8419:
8409:
8406:
8404:
8401:
8399:
8396:
8394:
8391:
8389:
8386:
8384:
8381:
8379:
8376:
8375:
8373:
8369:
8363:
8360:
8358:
8355:
8353:
8350:
8348:
8345:
8343:
8340:
8338:
8335:
8333:
8330:
8328:
8325:
8323:
8320:
8319:
8317:
8313:
8310:
8307:
8300:
8294:
8290:
8287:
8281:
8277:
8267:
8264:
8263:
8261:
8257:
8251:
8248:
8246:
8243:
8241:
8238:
8236:
8233:
8231:
8230:Dodecahedrane
8228:
8226:
8223:
8221:
8218:
8216:
8213:
8211:
8208:
8206:
8203:
8201:
8198:
8197:
8195:
8193:
8189:
8182:
8179:
8176:
8173:
8170:
8167:
8166:
8164:
8162:
8158:
8152:
8150:
8147:
8145:
8142:
8140:
8137:
8135:
8132:
8130:
8127:
8126:
8124:
8122:
8118:
8112:
8109:
8107:
8104:
8102:
8099:
8097:
8094:
8092:
8089:
8087:
8084:
8082:
8079:
8077:
8074:
8073:
8071:
8069:
8065:
8055:
8052:
8050:
8047:
8045:
8042:
8040:
8037:
8035:
8032:
8030:
8027:
8025:
8022:
8020:
8017:
8015:
8012:
8011:
8009:
8005:
7999:
7996:
7994:
7991:
7989:
7986:
7984:
7981:
7979:
7976:
7974:
7971:
7969:
7966:
7964:
7961:
7959:
7956:
7954:
7951:
7950:
7948:
7944:
7941:
7937:
7930:
7924:
7920:
7917:
7909:
7905:
7898:
7893:
7891:
7886:
7884:
7879:
7878:
7875:
7863:
7860:
7858:
7855:
7854:
7852:
7848:
7842:
7839:
7837:
7834:
7833:
7831:
7829:
7825:
7817:
7814:
7813:
7812:
7809:
7805:
7802:
7800:
7797:
7796:
7794:
7790:
7787:
7785:
7782:
7781:
7779:
7777:
7774:
7772:
7769:
7768:
7766:
7764:
7760:
7754:
7751:
7749:
7746:
7744:
7741:
7739:
7736:
7734:
7731:
7729:
7726:
7724:
7721:
7719:
7716:
7715:
7713:
7711:
7707:
7703:
7696:
7691:
7689:
7684:
7682:
7677:
7676:
7673:
7663:
7659:
7656:Compounds in
7653:
7647:
7644:
7642:
7639:
7637:
7634:
7632:
7629:
7628:
7626:
7622:
7616:
7615:
7611:
7609:
7606:
7604:
7603:
7599:
7597:
7594:
7592:
7589:
7587:
7584:
7582:
7581:
7577:
7575:
7572:
7571:
7569:
7567:Even–numbered
7565:
7561:
7554:
7549:
7547:
7542:
7540:
7535:
7534:
7531:
7525:
7522:
7520:
7517:
7514:
7513:Video Podcast
7511:
7509:
7506:
7504:
7500:
7497:
7495:
7492:
7490:
7487:
7485:
7482:
7479:
7478:
7473:
7470:
7469:
7464:
7463:
7462:
7456:
7452:
7419:
7415:
7411:
7405:
7389:
7385:
7384:
7379:
7373:
7364:
7359:
7355:
7351:
7347:
7340:
7324:
7320:
7319:
7314:
7308:
7301:
7297:
7292:
7285:
7281:
7278:
7273:
7266:
7262:
7259:
7254:
7247:
7243:
7240:
7235:
7228:
7223:
7215:
7211:
7207:
7203:
7199:
7195:
7191:
7187:
7180:
7172:
7168:
7164:
7160:
7156:
7152:
7144:
7136:
7132:
7128:
7124:
7120:
7116:
7115:
7106:
7098:
7094:
7090:
7086:
7083:(1–3): 7–17.
7082:
7078:
7071:
7063:
7059:
7054:
7049:
7045:
7041:
7037:
7033:
7029:
7022:
7015:
7011:
7007:
7001:
6994:
6988:
6980:
6976:
6972:
6968:
6964:
6960:
6956:
6948:
6930:
6926:
6922:
6918:
6914:
6910:
6906:
6899:
6892:
6877:
6873:
6869:
6863:
6847:
6843:
6839:
6833:
6821:
6817:
6813:
6809:
6802:
6796:
6794:
6777:
6773:
6769:
6763:
6747:
6743:
6739:
6733:
6731:
6714:
6710:
6706:
6700:
6693:
6689:
6686:
6681:
6674:
6670:
6667:
6662:
6654:
6650:
6645:
6640:
6636:
6632:
6629:(7): 437–44.
6628:
6624:
6620:
6613:
6607:
6603:
6600:
6594:
6586:
6582:
6579:(2): 157–68.
6578:
6574:
6567:
6559:
6555:
6550:
6545:
6541:
6537:
6534:(2): 213–21.
6533:
6529:
6525:
6518:
6511:
6507:
6504:
6500:
6494:
6486:
6482:
6477:
6472:
6467:
6462:
6458:
6454:
6450:
6443:
6436:
6431:
6423:
6419:
6414:
6409:
6405:
6401:
6397:
6393:
6389:
6382:
6380:
6371:
6367:
6362:
6357:
6352:
6347:
6343:
6339:
6335:
6331:
6327:
6320:
6313:
6309:
6306:
6301:
6294:
6290:
6286:
6282:
6276:
6268:
6262:
6258:
6254:
6250:
6243:
6235:
6229:
6225:
6221:
6214:
6200:on 2008-12-05
6199:
6195:
6189:
6180:
6166:on 2017-04-29
6165:
6161:
6155:
6140:
6136:
6130:
6115:
6111:
6110:
6105:
6098:
6090:
6086:
6081:
6076:
6072:
6068:
6064:
6057:
6042:
6038:
6034:
6028:
6013:
6009:
6005:
5999:
5984:
5980:
5976:
5970:
5962:
5958:
5954:
5950:
5946:
5942:
5938:
5934:
5927:
5919:
5915:
5910:
5905:
5901:
5897:
5894:(6139): 492.
5893:
5889:
5885:
5878:
5870:
5866:
5861:
5856:
5852:
5848:
5845:(6103): 396.
5844:
5840:
5836:
5829:
5821:
5817:
5813:
5809:
5805:
5801:
5797:
5793:
5786:
5778:
5774:
5770:
5766:
5762:
5758:
5751:
5743:
5739:
5735:
5731:
5727:
5723:
5719:
5715:
5711:
5707:
5703:
5699:
5698:
5693:
5686:
5667:
5663:
5659:
5655:
5651:
5646:
5641:
5637:
5633:
5629:
5625:
5624:
5616:
5609:
5601:
5597:
5593:
5589:
5584:
5579:
5575:
5571:
5567:
5563:
5559:
5555:
5554:
5546:
5539:
5527:
5523:
5522:
5517:
5510:
5502:
5496:
5492:
5488:
5484:
5477:
5475:
5466:
5462:
5458:
5454:
5450:
5446:
5442:
5438:
5431:
5424:
5420:
5416:
5415:archive.today
5412:
5409:
5403:
5396:
5392:
5388:
5387:archive.today
5384:
5381:
5375:
5369:
5365:
5359:
5352:
5348:
5344:
5340:
5336:
5333:
5327:
5313:
5309:
5302:
5287:
5282:
5277:
5273:
5269:
5265:
5261:
5260:
5255:
5248:
5239:
5234:
5230:
5226:
5222:
5218:
5217:
5212:
5208:
5202:
5194:
5190:
5183:
5175:
5171:
5167:
5163:
5159:
5155:
5148:
5133:
5129:
5125:
5121:
5117:
5113:
5106:
5098:
5094:
5090:
5086:
5083:(5): 266–67.
5082:
5078:
5070:
5062:
5060:9780486286907
5056:
5052:
5047:
5046:
5037:
5022:
5018:
5012:
5008:
5007:
4999:
4984:
4980:
4976:
4973:(2): 129–36.
4972:
4968:
4964:
4957:
4942:
4938:
4937:
4929:
4922:
4918:
4915:
4911:
4908:
4904:
4900:
4897:
4893:
4890:
4884:
4877:
4873:
4869:
4868:
4863:
4856:
4846:
4842:
4837:
4832:
4828:
4824:
4820:
4815:
4814:
4808:
4804:
4801:: 1604–1618.
4800:
4796:
4791:
4790:
4777:
4773:
4769:
4768:
4763:
4758:
4757:
4752:
4737:
4733:
4729:
4725:
4721:
4717:
4710:
4703:
4699:
4695:
4694:
4686:
4679:
4663:
4659:
4655:
4651:
4647:
4646:Kekulé, F. A.
4641:
4639:
4623:
4619:
4615:
4611:
4607:
4603:
4596:
4581:
4577:
4573:
4569:
4565:
4564:
4559:
4552:
4546:
4542:
4538:
4534:
4530:
4526:
4522:
4518:
4514:
4507:
4499:
4494:
4490:
4486:
4482:
4478:
4455:
4448:
4432:
4428:
4424:
4420:
4416:
4412:
4411:
4403:
4394:
4379:
4375:
4371:
4367:
4363:
4359:
4352:
4344:
4340:
4336:
4332:
4329:(in German).
4328:
4324:
4317:
4310:
4306:
4302:
4299:
4295:
4289:
4282:
4268:
4264:
4260:
4256:
4252:
4251:
4246:
4239:
4231:
4227:
4223:
4219:
4212:
4188:
4184:
4180:
4175:
4170:
4166:
4162:
4161:
4156:
4152:
4146:
4138:
4134:
4131:(4): 355–81.
4130:
4126:
4125:
4117:
4115:
4106:
4100:
4096:
4090:
4086:
4082:
4076:
4068:
4064:
4057:
4041:
4037:
4031:
4023:
4019:
4015:
4009:
4003:
3998:
3990:
3986:
3979:
3977:
3975:
3967:
3963:
3960:
3956:
3955:Sigma-Aldrich
3951:
3949:
3947:
3935:September 18,
3930:
3926:
3920:
3909:September 18,
3904:
3900:
3894:
3887:
3885:
3880:
3875:
3873:
3871:
3855:
3851:
3850:
3842:
3840:
3824:
3820:
3814:
3812:
3810:
3808:
3806:
3790:
3786:
3780:
3776:
3775:
3767:
3759:
3755:
3750:
3745:
3740:
3735:
3731:
3727:
3723:
3719:
3718:
3713:
3706:
3698:
3694:
3690:
3686:
3685:
3677:
3669:
3667:0-8493-0486-5
3663:
3659:
3652:
3644:
3638:
3634:
3630:
3626:
3622:
3615:
3613:
3608:
3593:
3589:
3585:
3581:
3577:
3573:
3570:
3563:
3559:
3549:
3545:
3541:
3537:
3533:
3529:
3525:
3521:
3517:
3516:stannabenzene
3513:
3509:
3505:
3501:
3499:
3498:
3494:
3492:
3489:
3487:
3484:
3483:
3479:
3468:
3465:
3459:
3454:
3447:
3445:
3441:
3437:
3427:
3424:
3422:
3418:
3417:Songhua River
3414:
3404:
3402:
3398:
3394:
3390:
3389:ascorbic acid
3386:
3380:
3370:
3366:
3352:
3350:
3349:benzene oxide
3340:
3338:
3333:
3323:
3319:
3317:
3313:
3309:
3305:
3301:
3297:
3293:
3289:
3285:
3281:
3277:
3273:
3269:
3264:
3262:
3258:
3254:
3250:
3246:
3242:
3238:
3234:
3230:
3226:
3216:
3214:
3210:
3206:
3202:
3198:
3194:
3178:
3175:
3173:
3169:
3165:
3161:
3156:
3154:
3149:
3147:
3143:
3139:
3135:
3131:
3121:
3119:
3115:
3111:
3107:
3103:
3101:
3097:
3093:
3088:
3086:
3082:
3078:
3074:
3070:
3066:
3061:
3057:
3053:
3049:
3045:
3041:
3037:
3033:
3023:
3021:
3017:
3013:
3009:
3003:
3001:
2997:
2993:
2989:
2985:
2980:
2978:
2974:
2970:
2966:
2957:
2948:
2946:
2940:
2925:
2921:
2911:
2909:
2905:
2901:
2897:
2893:
2889:
2888:hydrogenation
2882:Hydrogenation
2879:
2877:
2876:chlorobenzene
2873:
2869:
2861:
2857:
2853:
2849:
2845:
2831:
2827:
2825:
2821:
2817:
2814:
2810:
2809:acyl chloride
2806:
2802:
2798:
2794:
2790:
2780:
2776:
2775:
2774:
2773:
2772:
2770:
2759:
2755:
2754:
2753:
2751:
2747:
2743:
2739:
2729:
2727:
2722:
2720:
2716:
2712:
2711:United States
2708:
2704:
2700:
2699:octane rating
2696:
2658:
2655:
2651:
2649:
2645:
2641:
2637:
2633:
2629:
2625:
2620:
2616:
2612:
2608:
2604:
2600:
2596:
2592:
2588:
2587:alkylbenzenes
2584:
2574:
2572:
2571:mellitic acid
2568:
2564:
2560:
2556:
2552:
2549:derived from
2548:
2544:
2540:
2536:
2532:
2525:Other methods
2522:
2520:
2516:
2515:
2510:
2506:
2502:
2498:
2489:
2487:
2483:
2482:Selective TDP
2479:
2477:
2472:
2467:
2465:
2461:
2457:
2447:
2444:
2442:
2437:
2359:
2358:
2357:
2355:
2330:
2322:
2314:
2301:
2285:
2277:
2269:
2256:
2243:
2230:
2229:
2228:
2226:
2221:
2218:
2214:
2210:
2206:
2202:
2192:
2190:
2186:
2181:
2179:
2175:
2171:
2167:
2163:
2159:
2155:
2151:
2147:
2144:
2140:
2136:
2126:
2124:
2120:
2116:
2112:
2102:
2100:
2096:
2092:
2088:
2076:
2072:
2068:
2063:
2061:
2057:
2053:
2049:
2045:
2025:
2017:
2013:
2009:
2005:
1999:
1998:Alkylbenzenes
1995:
1985:
1983:
1979:
1974:
1972:
1968:
1964:
1959:
1955:
1951:
1947:
1943:
1939:
1935:
1927:
1922:
1912:
1910:
1906:
1902:
1898:
1894:
1890:
1880:
1878:
1874:
1870:
1869:liquid wrench
1866:
1862:
1859:
1855:
1845:
1843:
1839:
1834:
1824:
1822:
1818:
1814:
1811:
1806:
1804:
1800:
1796:
1791:
1779:
1774:
1773:
1772:
1770:
1766:
1762:
1757:
1752:
1749:
1745:
1741:
1737:
1733:
1729:
1719:
1715:
1712:
1708:
1705:
1701:
1696:
1692:
1689:
1685:
1682:
1678:
1677:
1673:
1672:August Kekulé
1664:
1659:
1655:
1651:
1648:
1644:
1641:
1637:
1632:
1628:
1625:
1621:
1618:
1614:
1613:
1608:
1600:
1598:
1594:
1590:
1586:
1582:
1577:
1575:
1571:
1567:
1563:
1559:
1555:
1551:
1547:
1544:
1540:
1536:
1532:
1528:
1524:
1520:
1519:benzoin resin
1516:
1512:
1497:
1495:
1491:
1487:
1483:
1479:
1474:
1472:
1468:
1464:
1460:
1456:
1452:
1448:
1444:
1440:
1436:
1432:
1427:
1425:
1421:
1417:
1413:
1409:
1405:
1393:
1389:
1386:
1382:
1370:
1363:
1358:
1341:
1335:
1332:
1328:
1323:
1320:
1316:
1313:
1308:
1307:
1302:
1299:
1296:
1293:
1290:
1289:
1285:
1281:
1277:
1276:
1272:
1269:(Recommended)
1268:
1264:
1263:
1259:
1256:(Permissible)
1255:
1251:
1250:
1246:
1245:
1240:
1230:
1226:
1217:
1216:
1212:
1208:
1199:
1198:
1194:
1190:
1186:
1184:
1181:
1180:
1176:
1173:
1167:
1166:
1162:
1160:
1157:
1156:
1149:
1142:
1135:
1111:
1108:
1107:
1103:
1102:
1076:
1073:
1069:
1068:
1026:
1023:
1019:
1018:
1015:
1012:
1009:
1005:
1004:
1000:
995:
990:
985:
980:
976:
973:
969:
968:
964:
962:
957:
953:
948:
947:
943:
942:
937:
932:
928:
920:
912:
906:
905:
901:
893:
885:
879:
878:
874:
866:
861:
855:
854:
850:
845:
840:
839:Heat capacity
836:
835:
830:
827:
823:
820:
819:Dipole moment
816:
815:
812:
809:
806:
802:
801:
796:
786:
782:
780:
777:
776:
770:
763:
759:
755:
754:
750:
746:
742:
741:
737:
730:
727:
726:
723:
720:
718:
715:
714:
711:
708:
706:
703:
702:
694:
692:
689:
688:
684:
682:
681:
676:
675:
671:
669:
665:
662:
661:
653:
651:
647:
644:
643:
637:
635:
631:
628:
627:
619:
617:
613:
610:
609:
606:
602:
598:
597:diethyl ether
594:
587:
580:
576:
574:
571:
570:
552:
549:
545:
544:
540:
538:
537:Boiling point
535:
534:
530:
528:
527:Melting point
525:
524:
520:
518:
515:
514:
510:
508:
505:
504:
500:
497:
496:
489:
487:
484:
483:
468:
465:
461:
460:
455:
446:
445:
442:
435:
421:
420:
417:
410:
402:
398:
397:DTXSID3039242
394:
393:
391:
381:
377:
376:
369:
365:
364:
362:
360:
357:
356:
349:
348:
346:
344:
341:
340:
333:
329:
328:
326:
320:
316:
315:
308:
304:
303:
301:
299:
296:
295:
288:
287:
285:
283:
278:
277:
273:
269:
266:
264:
262:ECHA InfoCard
259:
258:
251:
247:
246:
244:
242:
239:
238:
231:
227:
226:
224:
222:
219:
218:
211:
207:
206:
204:
202:
199:
198:
191:
187:
186:
184:
180:
175:
174:
167:
163:
162:
160:
157:
153:
152:
147:
143:
134:
127:
119:
115:
110:
102:
97:
83:
79:
70:
66:
65:
61:
53:
48:
40:
33:
19:
14494:Immunotoxins
14379:
14362:Spectroscopy
14216:Astrobiology
14069:Formaldehyde
13961:Benzonitrile
13955:
13752:Acetaldehyde
13707:Methanethiol
13658:Acetonitrile
13563:Carbodiimide
13442:Formaldehyde
13437:Cyanoethynyl
13288:Iron cyanide
13283:Hydroperoxyl
13084:Nitric oxide
12910:
12909:
12880:
12737:Lavender oil
12479:Nitric oxide
12399:Cryofluorane
12358:
12344:Acetophenone
12302:Methaqualone
12297:Mecloqualone
12292:Mebroqualone
12282:Diproqualone
12277:Cloroqualone
12206:Glutethimide
12010:
11962:
11929:
11891:
11864:Testosterone
11829:Progesterone
11794:Hydroxydione
11743:Androsterone
11670:Acecarbromal
11575:constituents
11362:Cyclarbamate
11352:Carisoprodol
11124:Metaclazepam
11119:Menitrazepam
11109:Meclonazepam
11104:Lormetazepam
11034:Flutemazepam
10859:Ciclotizolam
10849:Carburazepam
10741:Thiobarbital
10701:Secobarbital
10666:Phetharbital
10646:Nealbarbital
10631:Methohexital
10616:Hexobarbital
10551:Butallylonal
10546:Butobarbital
10501:Barbexaclone
10496:Aprobarbital
10481:Allobarbital
10468:Barbiturates
10435:
10427:
10417:Petrichloral
10273:
10266:
10180:Vinyl halide
10137:
10067:Borinic acid
10062:Boronic acid
10039:Thioxanthate
9379:Hydrocarbons
9291:
9275:
9187:
9179:
9171:
9124:
9116:
9108:
9069:
9043:Pseudocumene
9007:Ethylbenzene
8988:
8980:
8972:
8903:Phenanthrene
8811:hydrocarbons
8686:Cycloheptyne
8676:Cyclopentyne
8666:Cyclopropyne
8658:Cycloalkynes
8575:Cycloheptene
8565:Cyclopentene
8555:Cyclopropene
8547:Cycloalkenes
8434:
8427:
8305:
8298:
8285:hydrocarbons
8266:Spiroalkanes
8096:Cycloheptane
8086:Cyclopentane
8076:Cyclopropane
8068:Cycloalkanes
7935:
7928:
7915:hydrocarbons
7904:Hydrocarbons
7835:
7738:Cycloheptene
7728:Cyclopentene
7718:Cyclopropene
7702:Cycloalkenes
7657:
7631:Cyclopropene
7624:Odd–numbered
7612:
7600:
7579:
7578:
7475:
7459:
7458:
7457:profile for
7454:
7422:. Retrieved
7413:
7404:
7392:. Retrieved
7381:
7372:
7353:
7349:
7339:
7327:. Retrieved
7318:The Guardian
7316:
7307:
7299:
7291:
7272:
7253:
7234:
7222:
7189:
7185:
7179:
7154:
7150:
7143:
7118:
7114:Toxicol Lett
7112:
7105:
7080:
7076:
7070:
7035:
7031:
7021:
7005:
7000:
6992:
6987:
6954:
6947:
6936:. Retrieved
6908:
6904:
6891:
6880:. Retrieved
6871:
6862:
6852:November 23,
6850:. Retrieved
6846:the original
6832:
6820:the original
6780:. Retrieved
6776:the original
6762:
6752:November 23,
6750:. Retrieved
6746:the original
6717:. Retrieved
6713:the original
6699:
6680:
6661:
6626:
6622:
6612:
6593:
6576:
6572:
6566:
6531:
6527:
6517:
6493:
6456:
6452:
6442:
6430:
6395:
6391:
6333:
6329:
6319:
6300:
6284:
6280:
6275:
6248:
6242:
6219:
6213:
6202:. Retrieved
6198:the original
6188:
6179:
6168:. Retrieved
6164:the original
6154:
6143:. Retrieved
6129:
6118:, retrieved
6107:
6097:
6070:
6066:
6056:
6045:. Retrieved
6027:
6016:. Retrieved
6007:
5998:
5987:. Retrieved
5978:
5969:
5936:
5932:
5926:
5891:
5887:
5877:
5842:
5838:
5828:
5795:
5791:
5785:
5760:
5756:
5750:
5701:
5695:
5685:
5673:. Retrieved
5627:
5621:
5608:
5557:
5551:
5545:
5537:
5530:. Retrieved
5519:
5509:
5482:
5440:
5436:
5430:
5422:
5418:
5402:
5394:
5390:
5374:
5363:
5358:
5350:
5346:
5342:
5326:
5315:. Retrieved
5311:
5301:
5290:. Retrieved
5263:
5257:
5247:
5220:
5214:
5207:Lonsdale, K.
5201:
5192:
5188:
5182:
5160:(1): 21–23.
5157:
5153:
5147:
5136:. Retrieved
5119:
5115:
5105:
5080:
5076:
5069:
5044:
5036:
5025:. Retrieved
5005:
4998:
4987:. Retrieved
4970:
4966:
4956:
4945:. Retrieved
4935:
4928:
4920:
4916:
4891:
4888:
4883:
4865:
4855:
4826:
4822:
4798:
4794:
4780:. Retrieved
4771:
4765:
4751:
4740:. Retrieved
4726:: 258–268 .
4723:
4719:
4709:
4691:
4678:
4666:. Retrieved
4657:
4653:
4626:. Retrieved
4609:
4605:
4595:
4584:. Retrieved
4567:
4561:
4551:
4524:
4520:
4512:
4506:
4480:
4476:
4454:
4434:
4414:
4408:
4402:
4393:
4382:. Retrieved
4365:
4361:
4351:
4330:
4326:
4316:
4308:
4293:
4288:
4280:
4271:. Retrieved
4257:(1): 39–48.
4254:
4248:
4238:
4221:
4217:
4211:
4191:. Retrieved
4164:
4158:
4145:
4128:
4122:
4094:
4085:frankincense
4080:
4075:
4066:
4056:
4044:. Retrieved
4039:
4030:
4017:
4008:
3997:
3933:. Retrieved
3919:
3907:. Retrieved
3893:
3882:
3858:. Retrieved
3848:
3827:. Retrieved
3793:. Retrieved
3773:
3766:
3724:(1): 167–9.
3721:
3715:
3705:
3688:
3682:
3676:
3657:
3651:
3620:
3591:
3587:
3583:
3579:
3562:
3540:thiopyrylium
3532:bismabenzene
3512:germabenzene
3495:
3433:
3425:
3410:
3385:benzoic acid
3382:
3367:
3363:
3346:
3329:
3320:
3308:benzoquinone
3296:microtubules
3284:hydroquinone
3265:
3257:succinyl CoA
3222:
3209:hydroquinone
3193:muconic acid
3189:
3176:
3157:
3150:
3127:
3104:
3089:
3085:breath tests
3029:
3004:
2981:
2962:
2917:
2885:
2868:Nitrobenzene
2841:
2793:alkyl halide
2786:
2771:of benzene.
2766:
2750:carbocations
2742:nucleophilic
2735:
2723:
2701:and reduces
2692:
2652:
2599:nitrobenzene
2583:ethylbenzene
2580:
2539:Benzoic acid
2535:halobenzenes
2528:
2512:
2495:
2485:
2481:
2475:
2470:
2468:
2459:
2453:
2445:
2438:
2434:
2351:
2198:
2182:
2168:, including
2143:bifunctional
2135:hydrocarbons
2132:
2108:
2087:structurally
2086:
2067:heterocycles
2064:
2052:phenanthrene
2001:
1975:
1942:bond lengths
1932:
1889:World War II
1886:
1858:decaffeinate
1851:
1842:Viktor Meyer
1830:
1827:Nomenclature
1807:
1802:
1798:
1787:
1753:
1746:in 1858 and
1725:
1674:(1865/1872)
1603:Ring formula
1578:
1570:hydroxylated
1568:", which is
1557:
1546:benzoic acid
1534:
1514:
1510:
1508:
1482:human health
1475:
1459:ethylbenzene
1428:
1380:
1379:
1243:
1192:
1170:Autoignition
1105:
1013:
960:
950:Main hazards
939:
918:
902:48.7 kJ/mol
891:
864:
843:
761:
679:
343:RTECS number
230:ChEMBL277500
149:Identifiers
141:
132:
129:Other names
14464:Carcinogens
14336:Outer space
14246:Cosmic dust
14211:Abiogenesis
14123:Unconfirmed
14079:Heavy water
13919:Ethanethiol
13834:Cyanoallene
13824:Acetic acid
13794:Methylamine
13678:Diacetylene
13593:Formic acid
13583:Cyanomethyl
13241:Diazenylium
13231:CCP radical
13107:(molecular)
13091:(molecular)
13060:(molecular)
12819:Stiripentol
12814:Seproxetine
12784:Niacinamide
12764:Loreclezole
12585:Avermectins
12549:Vinyl ether
12519:Sevoflurane
12499:Paraldehyde
12449:Halopropane
12272:Afloqualone
12254:Tracazolate
12249:ICI-190,622
12239:Cartazolate
12216:Piperidione
12211:Methyprylon
12178:Fospropofol
12100:Pipequaline
11908:Pazinaclone
11898:Eszopiclone
11754:Cholesterol
11738:Androstenol
11662:Monoureides
11642:Methysticin
11442:Tetrabamate
11422:Pentabamate
11412:Meprobamate
11382:Febarbamate
11347:Carisbamate
11299:Triflubazam
11289:Tolufazepam
11249:Rilmazafone
11244:Remimazolam
11219:Proflazepam
11204:Pivoxazepam
11164:Nitrazepate
11154:Nimetazepam
11089:Lopirazepam
11059:Haloxazolam
11009:Fludiazepam
10954:Doxefazepam
10929:Delorazepam
10909:Clotiazepam
10904:Clorazepate
10869:Cinolazepam
10766:Vinbarbital
10721:Tetrabamate
10676:Probarbital
10656:Phenallymal
10621:Metharbital
10596:Febarbamate
10491:Amobarbital
10392:Isopropanol
10362:Chloralodol
10244:Thiocyanate
10239:Sulfonamide
10204:Perchlorate
10192:Acyl halide
10153:Fluoroethyl
10034:Thionoester
9922:Phosphonium
9907:Phosphinate
9902:Phosphonous
9890:Phosphonate
9589:Hydroperoxy
9411:Cyclopropyl
9091:C4-Benzenes
9048:Hemellitene
9021:C3-Benzenes
8955:C2-Benzenes
8918:Corannulene
8837:Naphthalene
8701:Cyclodecyne
8696:Cyclononyne
8691:Cyclooctyne
8681:Cyclohexyne
8671:Cyclobutyne
8590:Cyclodecene
8585:Cyclononene
8580:Cyclooctene
8570:Cyclohexene
8560:Cyclobutene
8280:Unsaturated
8111:Cyclodecane
8106:Cyclononane
8101:Cyclooctane
8091:Cyclohexane
8081:Cyclobutane
7753:Cyclodecene
7748:Cyclononene
7743:Cyclooctene
7733:Cyclohexene
7723:Cyclobutene
7157:(1): 9–20.
7121:(1): 22–8.
5583:1874/366378
5122:: 1302–11.
4774:: 101–105.
4612:: 140–142.
4167:: 440–466.
4151:Faraday, M.
3569:pages 86–89
3528:arsabenzene
3524:phosphorine
3508:silabenzene
3504:borabenzene
3436:Nazi German
3332:Glutathione
3312:polyphenols
3304:methylation
3233:dioxygenase
3016:teratogenic
3012:chromosomal
2892:cyclohexane
2844:Sulfonation
2715:groundwater
2619:Cyclohexane
2611:polystyrene
2595:cyclohexane
2585:(and other
2044:naphthalene
1971:aromaticity
1958:cyclohexane
1921:Aromaticity
1647:James Dewar
1550:gum benzoin
1537:. In 1833,
1527:sublimation
1515:gum benzoin
1424:hydrocarbon
1207:median dose
1193:Lethal dose
1172:temperature
1159:Flash point
1008:Signal word
944:(OHS/OSH):
605:acetic acid
577:Soluble in
498:Appearance
457:Properties
268:100.000.685
210:CHEBI:16716
14534:Teratogens
14438:Categories
14251:Cosmic ray
14193:Silylidyne
14156:Hemolithin
14131:Anthracene
14048:Deuterated
14029:Pyrimidine
13839:Ethanimine
13702:Ketenimine
13558:Butadiynyl
13382:Thioformyl
13236:Chloronium
12852:Topiramate
12842:Terpenoids
12799:Propanidid
12789:Org 25,435
12717:Flupirtine
12712:Fluoxetine
12618:Chloralose
12589:ivermectin
12494:Norflurane
12459:Isoflurane
12404:Desflurane
12394:Chloroform
12354:Aliflurane
12287:Etaqualone
12115:SB-205,384
12045:CP-615,003
12040:CL-218,872
11994:Panadiplon
11984:Lorediplon
11913:Suproclone
11874:Zuranolone
11834:Renanolone
11819:Posovolone
11799:Minaxolone
11789:Ganaxolone
11728:Alfaxalone
11723:Alfadolone
11713:Acebrochol
11680:Bromisoval
11558:Metomidate
11545:Imidazoles
11505:Hispidulin
11457:Flavonoids
11417:Nisobamate
11407:Mebutamate
11377:Ethinamate
11372:Emylcamate
11339:Carbamates
11309:Tuclazepam
11284:Tetrazepam
11239:Reclazepam
11214:Premazepam
11194:Phenazepam
11174:Nordazepam
11169:Nitrazolam
11159:Nitrazepam
11139:Motrazepam
11094:Loprazolam
11084:Lofendazam
11069:Imidazenil
11029:Flutazolam
11024:Flurazepam
10994:Fletazepam
10949:Dimdazenil
10944:Diclazepam
10924:Cyprazepam
10914:Cloxazolam
10894:Clonazolam
10889:Clonazepam
10879:Climazolam
10839:Brotizolam
10834:Bromazolam
10829:Bromazepam
10824:Bretazenil
10819:Bentazepam
10809:Arfendazam
10804:Alprazolam
10799:Adinazolam
10771:Vinylbital
10751:Thiopental
10626:Methitural
10541:Buthalital
10536:Butalbital
10387:Isobutanol
10148:Haloalkane
10019:Thioketone
9974:Persulfide
9870:Phosphorus
9835:Isocyanate
9825:Isonitrile
9726:or oxygen
9724:hydrogen,
9720:not being
9701:Orthoester
9594:Dioxiranes
9572:Enol ether
9460:1-Propenyl
9150:Prehnitene
9038:Mesitylene
8893:Circulenes
8842:Anthracene
8770:Alkatriene
8739:Heptadiene
8729:Pentadiene
8719:Propadiene
8648:Norbornene
8518:Isoheptyne
8508:Isopentyne
8393:Isoheptene
8383:Isopentene
8205:Diamondoid
8200:Adamantane
8175:Norbornane
8039:Isoheptane
8029:Neopentane
8019:Isopentane
7014:0962652377
6938:2010-08-25
6882:2011-11-23
6782:October 9,
6398:: 133–48.
6293:0071402357
6266:3527306730
6204:2008-06-27
6170:2015-02-10
6145:2015-02-10
6120:August 13,
6073:: 106541.
6047:2016-07-08
6018:2009-01-16
5989:2009-01-16
5675:January 4,
5317:2022-03-01
5292:2007-03-12
5195:(1): 1–40.
5138:2007-03-12
5027:2020-05-15
4989:2021-12-25
4947:2015-06-27
4923:: 129–143.
4782:2018-02-17
4742:2015-06-27
4668:2015-06-27
4660:: 98–110.
4628:2015-06-27
4586:2015-06-27
4384:2015-06-27
4273:2015-06-27
4193:2012-01-15
4081:luban jawi
3860:2015-06-27
3829:2014-05-29
3795:2012-05-31
3603:References
3360:Inhalation
3253:acetyl CoA
3229:eukaryotes
3181:Toxicology
3132:has set a
3052:pesticides
3048:lubricants
2965:carcinogen
2856:detergents
2813:Lewis acid
2769:ethylation
2648:pesticides
2644:explosives
2636:detergents
2628:lubricants
2503:and other
2213:molybdenum
2162:extraction
2105:Production
2095:pyrimidine
2091:pyridazine
2048:anthracene
1963:π orbitals
1938:picometres
1883:Occurrence
1871:, several
1838:Carl Gräbe
1543:distilling
1509:The word "
1478:carcinogen
972:Pictograms
911:combustion
798:Structure
664:Solubility
646:Solubility
630:Solubility
616:ethanediol
612:Solubility
573:Solubility
486:Molar mass
368:J64922108F
241:ChemSpider
177:3D model (
156:CAS Number
142:(historic)
14449:Annulenes
14183:Phosphine
14051:molecules
13984:fullerene
13884:Acetamide
13688:Formamide
13568:Cyanamide
13422:Acetylene
13397:Tricarbon
13308:Methylene
13293:Isoformyl
13198:Triatomic
12971:Molecules
12911:See also:
12873:valerenol
12794:Phenytoin
12774:Monastrol
12732:Lanthanum
12727:KRM-II-81
12690:Fenamates
12685:Etifoxine
12680:Etazepine
12675:Efavirenz
12633:Darigabat
12529:Teflurane
12514:Roflurane
12509:Propylene
12454:Halothane
12439:Fluroxene
12424:Enflurane
12327:Volatiles
12244:Etazolate
12155:Viqualine
12110:RWJ-51204
12075:L-838,417
12065:Imepitoin
12035:CGS-20625
12030:CGS-13767
12015:Adipiplon
11989:Ocinaplon
11951:Saripidem
11946:Necopidem
11923:Zopiclone
11918:Suriclone
11903:Pagoclone
11809:ORG-21465
11804:ORG-20599
11695:Ectylurea
11685:Carbromal
11563:Propoxate
11553:Etomidate
11480:Baicalein
11437:Styramate
11432:Procymate
11402:Lorbamate
11387:Felbamate
11357:Clocental
11329:Zomebazam
11324:Zolazepam
11319:Zapizolam
11314:Uldazepam
11294:Triazolam
11279:Temazepam
11274:Sulazepam
11264:Ro48-8684
11259:Ro48-6791
11254:Ripazepam
11224:Pyrazolam
11199:Pinazepam
11149:Nifoxipam
11134:Midazolam
11129:Mexazolam
11114:Medazepam
11099:Lorazepam
11079:Ketazolam
11074:Irazepine
11064:Iclazepam
11054:Halazepam
11049:Gidazepam
11044:Fosazepam
10964:Estazolam
10959:Elfazepam
10934:Demoxepam
10864:Cinazepam
10844:Camazepam
10814:Avizafone
10736:Thiamylal
10671:Primidone
10601:Heptabarb
10591:Eterobarb
10556:Carbubarb
10453:Triclofos
10352:Brometone
10281:inorganic
10115:Tellurium
10029:Thioester
9994:Sulfoxide
9979:Disulfide
9967:Sulfonium
9917:Phosphine
9895:Phosphite
9878:Phosphate
9810:Carbamate
9785:Hydrazone
9718:element,
9716:Only one
9689:Anhydride
9428:Methylene
9319:Annulynes
9314:Annulenes
9155:Isodurene
8888:Helicenes
8862:Heptacene
8852:Pentacene
8847:Tetracene
8775:Alkadiyne
8754:Decadiene
8749:Nonadiene
8744:Octadiene
8734:Hexadiene
8724:Butadiene
8533:Isodecyne
8528:Isononyne
8523:Isooctyne
8513:Isohexyne
8408:Isodecene
8403:Isononene
8398:Isooctene
8388:Isohexene
8378:Isobutene
8283:aliphatic
8240:Churchane
8235:Basketane
8054:Isodecane
8049:Isononane
8044:Isooctane
8034:Isohexane
8014:Isobutane
7913:aliphatic
7911:Saturated
7850:Tetraenes
7560:Annulenes
7329:7 January
7151:Mutat Res
6719:April 17,
6089:1566-7367
5726:2053-9169
4570:: 82–86.
4014:"Benzene"
3440:injection
3158:The U.S.
3151:The U.S.
3096:leukaemia
3020:mutagenic
2860:nitration
2805:acylation
2732:Reactions
2563:acetylene
2473:-xylene (
2294:⟶
2203:converts
2174:sulfolane
2158:aliphatic
2152:chloride
1915:Structure
1852:In 1903,
1795:ouroboros
1579:In 1845,
1505:Discovery
1455:precursor
1447:flammable
1431:petroleum
1414:with one
1390:with the
1187:1.2–7.8%
1094:P308+P313
1086:P301+P310
963:labelling
884:formation
858:Std molar
779:Viscosity
722:Benzenide
710:Benzenium
350:CY1400000
289:200-753-7
281:EC Number
14499:Mutagens
14170:Linear C
14151:Graphene
14063:Ammonium
13864:Acrolein
13727:Propynal
13712:Methanol
13683:Ethylene
13552:Ammonium
13327:Nitroxyl
13151:Sulfanyl
13095:Imidogen
13089:Nitrogen
13058:Hydrogen
13003:Argonium
12980:Diatomic
12899:TCS-1205
12894:TCS-1105
12884:α-Pinene
12857:Valerian
12832:tetronal
12809:Safranal
12758:obovatol
12754:magnolol
12750:honokiol
12580:Alogabat
12575:AA-29504
12524:Synthane
12484:Nitrogen
12464:Kerosine
12444:Gasoline
12434:Ethylene
12374:Centalun
12369:Butylene
12183:Propofol
12145:U-89843A
12125:TGSC01AA
12095:NS-11394
12060:GBLD-345
12025:CGS-9896
12020:CGS-8216
12004:Zaleplon
11999:Taniplon
11979:Indiplon
11974:Fasiplon
11969:Divaplon
11956:Zolpidem
11859:SAGE-872
11854:SAGE-689
11849:SAGE-516
11844:SAGE-324
11839:SAGE-105
11747:Certain
11690:Capuride
11652:Yangonin
11529:baicalin
11525:Skullcap
11515:Luteolin
11490:Catechin
11485:Baicalin
11475:Apigenin
11447:Tybamate
11234:Quazepam
11229:QH-II-66
11209:Prazepam
11189:Oxazolam
11184:Oxazepam
10984:Etizolam
10939:Diazepam
10919:CP-1414S
10884:Clobazam
10874:Clazolam
10761:Valofane
10716:Talbutal
10706:Sigmodal
10611:Hexethal
10506:Barbital
10486:Alphenal
10476:(-)-DMBB
10422:Propanol
10412:Pentanol
10402:Methanol
10344:Alcohols
10262:See also
10197:Chloride
10123:Tellurol
10077:Selenium
10044:Xanthate
9758:Ammonium
9740:Nitrogen
9722:carbon,
9679:Carboxyl
9646:Aldehyde
9634:Acryloyl
9616:carbonyl
9520:hydrogen
9475:Cumulene
8923:Kekulene
8908:Chrysene
8898:Butalene
8883:Fluorene
8857:Hexacene
8809:Aromatic
8780:Cumulene
8250:Twistane
8245:Pagodane
8225:Prismane
7662:aromatic
7455:chemical
7418:Archived
7388:Archived
7323:Archived
7300:CBS News
7280:Archived
7261:Archived
7242:Archived
7214:36885673
7206:18836923
7135:19427373
7097:18848868
6979:15935823
6929:Archived
6876:Archived
6688:Archived
6669:Archived
6602:Archived
6585:16161967
6558:17718179
6506:Archived
6485:20070208
6422:20070208
6370:24932584
6336:(6): 6.
6330:PLOS ONE
6308:Archived
6139:Archived
6114:archived
6041:Archived
6012:Archived
5983:Archived
5918:45218186
5820:24349360
5777:16848464
5742:94432897
5666:Archived
5662:46983230
5654:29880683
5600:46952468
5592:29880670
5526:Archived
5465:32311057
5457:17558801
5411:Archived
5383:Archived
5368:p. 1142.
5335:Archived
5286:Archived
5209:(1929).
5132:Archived
5021:Archived
4983:Archived
4941:Archived
4910:Archived
4899:Archived
4845:16218557
4776:Archived
4736:Archived
4662:Archived
4648:(1865).
4622:Archived
4580:Archived
4431:97105342
4378:Archived
4343:Archived
4301:Archived
4267:Archived
4187:Archived
4153:(1825).
4024:(NIOSH).
3991:(NIOSH).
3962:Archived
3854:Archived
3823:Archived
3819:"Benzol"
3789:Archived
3572:Archived
3536:pyrylium
3520:pyridine
3450:See also
3430:Genocide
3288:catechol
3249:catechol
3225:bacteria
3205:catechol
2977:leukemia
2896:hydrogen
2818:such as
2816:catalyst
2703:knocking
2695:gasoline
2501:ethylene
2454:Toluene
2354:biphenyl
2217:platinum
2209:chromium
2199:Toluene
2166:solvents
2154:catalyst
2139:hydrogen
2099:pyrazine
2075:pyridine
2071:nitrogen
2060:graphite
2024:biphenyl
1901:polymers
1736:hydrogen
1593:aromatic
1589:coal tar
1494:leukemia
1451:gasoline
1439:pi bonds
1416:hydrogen
1404:molecule
1319:Borazine
1286:500 ppm
1106:NFPA 704
934:Hazards
747:(χ)
448:c1ccccc1
76:Geometry
45:Benzene
18:Benzenes
14444:Benzene
14316:Kerogen
14203:Related
14146:Glycine
14099:Propyne
14058:Ammonia
13956:Benzene
13951:Acetone
13943:or more
13914:Propene
13899:Ethanol
13789:Propyne
13608:Methane
13477:Ketenyl
13427:Ammonia
12846:borneol
12844:(e.g.,
12836:trional
12826:(e.g.,
12744:(e.g.,
12742:Lignans
12692:(e.g.,
12650:(e.g.,
12595:Bromide
12587:(e.g.,
12570:α-EMTBL
12534:Toluene
12504:Propane
12379:Chloral
12359:Benzene
12339:Acetone
12170:Phenols
12160:Y-23684
12150:U-90042
12135:TPA-023
12120:SX-3228
12105:ROD-188
12090:NS-2710
12085:NS-2664
12070:JM-1232
12055:ELB-139
12050:CTP-354
11936:Alpidem
11535:Wogonin
11510:Linarin
10989:FG-8205
10696:Reposal
10397:Menthol
10357:Butanol
10286:organic
10085:Selenol
10009:Sulfone
9962:Sulfide
9860:NONOate
9855:Nitroso
9845:Nitrite
9840:Nitrate
9830:Cyanate
9820:Nitrile
9805:Amidine
9800:Imidate
9770:Nitrene
9765:Hydrazo
9753:Enamine
9684:Acetoxy
9672:carboxy
9639:Benzoyl
9577:Epoxide
9560:Methoxy
9550:Alcohol
9504:Carbene
9438:Methine
9276:Benzene
9250:Styrene
9127:-Cymene
9119:-Cymene
9111:-Cymene
9100:Cymenes
8991:-Xylene
8983:-Xylene
8975:-Xylene
8964:Xylenes
8945:Toluene
8878:Azulene
8477:Heptyne
8467:Pentyne
8457:Propyne
8422:Alkynes
8347:Heptene
8337:Pentene
8327:Propene
8293:Alkenes
8215:Sterane
8181:Decalin
8169:Housane
7983:Heptane
7973:Pentane
7963:Propane
7953:Methane
7923:Alkanes
7836:Benzene
7828:Trienes
7710:Alkenes
7658:italics
7580:Benzene
7503:PubChem
7499:Benzene
7472:Benzene
7461:Benzene
7451:Scholia
7424:May 11,
7414:Haaretz
7394:May 15,
7171:7517507
7062:9118888
7053:1469747
6959:Bibcode
6925:8013127
6814:(CDC),
6653:1854646
6644:1035396
6549:3363002
6476:4360999
6413:4360999
6361:4059738
6338:Bibcode
6283:(2004)
5961:4268597
5941:Bibcode
5896:Bibcode
5869:4261220
5847:Bibcode
5800:Bibcode
5734:2414835
5706:Bibcode
5632:Bibcode
5623:Science
5562:Bibcode
5553:Science
5532:June 8,
5268:Bibcode
5225:Bibcode
5162:Bibcode
5085:Bibcode
4545:p. 379.
4485:Bibcode
4417:: 1–3.
4083:", or "
3985:"#0049"
3959:Benzene
3929:PubChem
3903:PubChem
3879:Benzene
3758:2153285
3726:Bibcode
3444:killing
3310:toward
3060:tobacco
3044:rubbers
3000:Group 1
2922:in the
2872:aniline
2746:acylium
2726:Catalan
2654:Toluene
2624:rubbers
2607:styrene
2551:aniline
2505:alkenes
2478:-xylene
2441:xylenes
2225:methane
2205:toluene
2150:rhenium
2115:toluene
2016:aniline
2012:toluene
1978:Unicode
1763:of any
1720:(1899)
1713:(1888)
1706:(1887)
1656:(1869)
1649:(1869)
1642:(1867)
1511:benzene
1500:History
1385:organic
1381:Benzene
1362:what is
1360: (
1315:Toluene
860:entropy
787:(10 °C)
783:0.7528
738:255 nm
650:acetone
634:ethanol
601:acetone
579:alcohol
517:Density
319:PubChem
166:71-43-2
131:Benzol
122:Benzene
14367:Tholin
14188:Pyrene
13633:Silane
13603:Ketene
13105:Oxygen
12779:Niacin
12364:Butane
12317:SL-164
12188:Thymol
12130:TP-003
12011:Others
11814:P1-185
11774:5β-DHP
11769:5α-DHP
11764:3α-DHP
11612:Kavain
11520:Rc-OMe
10185:Iodide
10105:Selone
9949:Sulfur
9658:Ketone
9651:Ketene
9629:Acetyl
9584:Peroxy
9555:Alkoxy
9545:Acetal
9526:oxygen
9515:carbon
9499:Alkyne
9492:Benzyl
9487:Phenyl
9470:Allene
9465:Crotyl
9445:Alkene
9433:Bridge
9421:Pentyl
9406:Propyl
9396:Methyl
9145:Durene
9064:Cumene
8913:Pyrene
8829:Acenes
8711:Dienes
8492:Decyne
8487:Nonyne
8482:Octyne
8472:Hexyne
8462:Butyne
8452:Ethyne
8362:Decene
8357:Nonene
8352:Octene
8342:Hexene
8332:Butene
8322:Ethene
8220:Cubane
7998:Decane
7993:Nonane
7988:Octane
7978:Hexane
7968:Butane
7958:Ethane
7763:Dienes
7453:has a
7212:
7204:
7169:
7133:
7095:
7060:
7050:
7012:
6977:
6923:
6651:
6641:
6583:
6556:
6546:
6483:
6473:
6420:
6410:
6368:
6358:
6291:
6281:et al.
6263:
6230:
6087:
5959:
5933:Nature
5916:
5888:Nature
5867:
5839:Nature
5818:
5792:Nature
5775:
5740:
5732:
5724:
5660:
5652:
5598:
5590:
5497:
5463:
5455:
5057:
5053:–180.
5013:
4843:
4541:p. 354
4537:p. 326
4533:p. 320
4529:p. 317
4429:
4183:107752
4181:
4101:
4046:16 Aug
3781:
3756:
3746:
3664:
3639:
3413:Harbin
3280:phenol
3276:oxepin
3237:oxygen
3201:phenol
3110:cancer
3098:, and
3092:anemia
3083:, and
3036:phenol
2969:cancer
2920:ligand
2904:nickel
2858:. In
2646:, and
2615:phenol
2597:, and
2591:cumene
2531:Phenol
2464:xylene
2056:pyrene
2054:, and
2014:, and
2008:phenol
1954:hexane
1950:alkane
1861:coffee
1815:using
1761:isomer
1740:carbon
1574:phenyl
1566:phenol
1558:benzin
1552:) and
1548:(from
1523:acidic
1463:cumene
1420:carbon
1408:carbon
1383:is an
1357:verify
1354:
1294:(SDS)
1014:Danger
729:UV-vis
491:78.114
441:SMILES
307:C01407
221:ChEMBL
140:Phene
112:Names
14353:(PAH)
13941:atoms
13876:atoms
13816:atoms
13814:Eight
13744:atoms
13742:Seven
13650:atoms
13544:atoms
13414:atoms
13402:Water
13332:Ozone
13274:(HNC)
13268:(HCN)
12638:DEABL
12331:gases
12140:TP-13
11869:THDOC
11759:DHDOC
10217:Other
10054:Boron
10024:Thial
9957:Thiol
9850:Nitro
9815:Imide
9795:Amide
9780:Oxime
9775:Imine
9748:Amine
9696:Ester
9663:Ynone
9567:Ether
9538:R-O-R
9513:Only
9455:Allyl
9450:Vinyl
9416:Butyl
9401:Ethyl
9391:Alkyl
9307:Other
9292:trans
9269:Other
9208:Other
9164:Other
9057:Other
9000:Other
8871:Other
8795:Enyne
8763:Other
8259:Other
7501:from
7210:S2CID
6932:(PDF)
6901:(PDF)
6823:(PDF)
6804:(PDF)
6497:WHO.
5957:S2CID
5914:S2CID
5865:S2CID
5816:S2CID
5738:S2CID
5730:JSTOR
5669:(PDF)
5658:S2CID
5618:(PDF)
5596:S2CID
5461:S2CID
4688:(PDF)
4427:S2CID
4298:p. 44
4179:JSTOR
3957:Co.,
3749:53221
3114:NIOSH
3081:blood
3077:urine
3065:urine
2848:oleum
2693:As a
2640:drugs
2553:with
2507:from
2220:oxide
2215:, or
2123:ATSDR
2097:, or
1897:steel
1865:Sanka
1244:NIOSH
685:2.13
416:InChI
201:ChEBI
179:JSmol
13874:Nine
13542:Five
13452:HCCN
13412:Four
13372:SiNC
11941:DS-1
11573:Kava
11500:EGCG
10436:tert
10428:tert
10331:GABA
10139:Halo
9624:Acyl
9524:and
9482:Aryl
9188:tert
8820:PAHs
7660:are
7426:2019
7396:2020
7331:2020
7202:PMID
7167:PMID
7131:PMID
7093:PMID
7058:PMID
7010:ISBN
6975:PMID
6921:PMID
6854:2011
6784:2010
6754:2011
6721:2014
6649:PMID
6581:PMID
6554:PMID
6481:PMID
6418:PMID
6366:PMID
6289:ISBN
6261:ISBN
6228:ISBN
6122:2021
6085:ISSN
5773:PMID
5722:ISSN
5677:2021
5650:PMID
5588:PMID
5534:2018
5495:ISBN
5453:PMID
5264:133A
5221:123A
5055:ISBN
5011:ISBN
4841:PMID
4441:n2-8
4099:ISBN
4089:Java
4048:2023
4002:MSDS
3937:2022
3911:2022
3779:ISBN
3754:PMID
3662:ISBN
3637:ISBN
3486:BTEX
3434:The
3255:and
3245:diol
3241:NADH
3227:and
3211:and
3146:MCLG
3128:The
3106:OSHA
3056:dyes
3018:and
2982:The
2941:and
2928:Cr(C
2886:Via
2632:dyes
2577:Uses
2533:and
2471:para
2187:and
1996:and
1909:Mars
1893:coke
1726:The
1554:lime
1461:and
1412:ring
1298:HMDB
1280:IDLH
1098:P331
1082:P210
1078:P201
1064:H410
1060:H372
1056:H350
1052:H340
1048:H319
1044:H315
1040:H305
1036:H304
1032:H302
1028:H225
678:log
583:CHCl
507:Odor
359:UNII
298:KEGG
14165:NCO
14065:ion
13972:, C
13939:Ten
13648:Six
13554:ion
12670:DS2
11779:DHT
11495:EGC
9790:Azo
9180:sec
8437:− 2
7938:+ 2
7474:at
7358:doi
7194:doi
7159:doi
7155:322
7123:doi
7119:192
7085:doi
7081:182
7048:PMC
7040:doi
7036:104
6967:doi
6913:doi
6639:PMC
6631:doi
6544:PMC
6536:doi
6471:PMC
6461:doi
6408:PMC
6400:doi
6356:PMC
6346:doi
6253:doi
6075:doi
6071:172
5949:doi
5937:329
5904:doi
5892:329
5855:doi
5843:325
5808:doi
5796:323
5765:doi
5761:128
5714:doi
5702:279
5640:doi
5628:360
5578:hdl
5570:doi
5558:360
5487:doi
5445:doi
5423:156
5395:149
5276:doi
5233:doi
5170:doi
5124:doi
5093:doi
5051:179
4975:doi
4971:137
4921:319
4892:306
4872:doi
4831:doi
4827:105
4803:doi
4799:127
4728:doi
4698:doi
4614:doi
4572:doi
4543:or
4493:doi
4481:546
4467:, C
4419:doi
4370:doi
4335:doi
4259:doi
4226:doi
4169:doi
4165:115
4133:doi
4091:".
4087:of
4040:CDC
3744:PMC
3734:doi
3693:doi
3629:doi
3592:one
3584:162
3395:in
3300:DNA
3282:to
3008:DNA
3002:).
2994:or
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