1038:, which disturbs the metabolism of hemoglobin and results in skin lesions. Almost all breastfeeding children under the age of two, whose mothers had eaten tainted bread, died from a condition called "pembe yara" or "pink sore", most likely from high doses of HCB in the breast milk. In one mother's breast milk the HCB level was found to be 20 parts per million in lipid, approximately 2,000 times the average levels of contamination found in breast-milk samples around the world. Follow-up studies 20 to 30 years after the poisoning found average HCB levels in breast milk were still more than seven times the average for unexposed women in that part of the world (56 specimens of human milk obtained from mothers with porphyria, average value was 0.51 ppm in HCB-exposed patients compared to 0.07 ppm in unexposed controls), and 150 times the level allowed in cow's milk.
295:
200:
38:
28:
889:
1042:
hyperpigmentation (65%), hypertrichosis (44.8%), pinched faces (40.1%), painless arthritis (70.2%), small hands (66.6%), sensory shading (60.6%), myotonia (37.9%), cogwheeling (41.9%), enlarged thyroid (34.9%), and enlarged liver (4.8%). Urine and stool porphyrin levels were determined in all patients, and 17 have at least one of the porphyrins elevated. Offspring of mothers with three decades of HCB-induced porphyria appear normal.
1385:
1366:
696:
Hexachlorobenzene is a stable, white, crystalline chlorinated hydrocarbon. It is sparingly soluble in organic solvents such as benzene, diethyl ether and alcohol, but practically insoluble in water with no reaction. It has a flash point of 468 °F and it is stable under normal temperatures and
1034:, Turkey between 1955 and 1959, during a period when bread wheat was unavailable, 500 people were fatally poisoned and more than 4,000 people fell ill by eating bread made with HCB-treated seed that was intended for agriculture use. Most of the sick were affected with a liver condition called
1041:
In the same follow-up study of 252 patients (162 males and 90 females, avg. current age of 35.7 years), 20–30 years' postexposure, many subjects had dermatologic, neurologic, and orthopedic symptoms and signs. The observed clinical findings include scarring of the face and hands (83.7%),
793:) had been removed, leaving the unwanted α- and β- isomers. This mixture is produced when benzene is reacted with chlorine in the presence of ultraviolet light (e.g. from sunlight). However, manufacture is no longer practiced following the compound's ban.
1778:
959:
and is considered to be a probable human carcinogen. After its introduction as a fungicide in 1945, for crop seeds, this toxic chemical was found in all food types. Hexachlorobenzene was banned from use in the United States in 1966.
1334:
Roscoe, H. E., Schorlemmer, C. (1887). The chemistry of the hydrocarbons and their derivatives, or
Organic chemistry. 1882-1892. 6 v. USA: D. Appleton. Pages 83-83
1501:
Fiege, Helmut; Voges, Heinz-Werner; Hamamoto
Toshikazu; Umemura Sumio; Iwata Tadao; Miki Hisaya; Fujita Yasuhiro; Buysch, Hans-Joseph; Garbe, Dorothea; Paulus, Wilfried (2012). "Phenol derivatives".
785:
Large-scale manufacture for use as a fungicide was developed by using the residue remaining after purification of the mixture of isomers of hexachlorocyclohexane, from which the insecticide
1763:
721:
Hexachlorobenzene was first known as "Julin's chloride of carbon" as it was discovered as a strange and unexpected product of impurities reacting in Julin's nitric acid factory. In 1864,
1667:
Peters, H.A., et al. Epidemiology of
Hexachlorobenzene-induced Porphyria in Turkey: Clinical and Laboratory Follow-up After 25 Years, Archives of Neurology 1982; 39(12): p. 744-749.
995:, thyroid effects, bone effects and loss of hair. Neurological changes have been reported in rodents exposed to hexachlorobenzene. Hexachlorobenzene may cause embryolethality and
1658:
Cripps, D.J., et al. Porphyria
Turcica Due to Hexachlorobenzene: A 20 to 30 Year Follow-up Study on 204 Patients, British Journal of Dermatology 1984; 111(4): p. 413-422.
1616:
Natural
Resources Defense Council (2001). Healthy Milk, Healthy Baby: Chemical Pollution and Mother's Milk. Retrieved September 13, 2008 from the World Wide Web:
685:
1383:, Becke, Friedrich & Sperber, Heinrich, "Process for the production of hexachlorobenzene", issued 1957-05-14, assigned to BASF
999:
effects. Human and animal studies have demonstrated that hexachlorobenzene crosses the placenta to accumulate in foetal tissues and is transferred in
1503:
1432:
1465:
722:
746:
952:
Material has relatively low acute toxicity but is toxic because of its persistent and cumulative nature in body tissues in rich lipid content.
733:, he then suggested that his compound was the same as Julin's chloride of carbon. Müller previously also believed it was the same compound as
1575:
344:
964:
697:
pressures. It is combustible but it does not ignite readily. When heated to decomposition, hexachlorobenzene emits highly toxic fumes of
749:
proved that the compound produced from benzene and antimony was the same as Julian's carbon chloride and named it "hexachlorobenzene".
1014:. Therefore, release into waterways should be avoided. It is persistent in the environment. Ecological investigations have found that
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Environmental Health
Criteria No 195; International Programme on Chemical Safety, World health Organization, Geneva, 1997.
1401:"CXXXV.—Studies in chlorination. III. The progressive chlorination of benzene in presence of the aluminium-mercury couple"
797:
1773:
1758:
1520:
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906:
856:
1628:
Jensen, A.A. and S.A. Slorach. Chemical
Contaminants in Human Milk, 1991, Boca Raton Ann Arbor Boston: CRC Press, Inc.
1753:
1553:
928:
309:
1430:
Beck, Uwe; Löser, Eckhard (2012). "Chlorinated benzenes and other nucleus-chlorinated aromatic hydrocarbons".
1364:, Ligett, Waldo B., "Manufacture of hexachlorobenzene", issued 1956-12-04, assigned to Ethyl Corp
971:(possibly carcinogenic to humans). Animal carcinogenicity data for hexachlorobenzene show increased incidences of
641:
27:
910:
1649:
Gocmen, A., et al. Hexachlorobenzene
Episode in Turkey, Biomedical Environmental Science 1989; 2(1): p. 36-43.
1018:
up the food chain does occur. Hexachlorobenzene has a half life in the soil of between 3 and 6 years. Risk of
1768:
1743:
1733:
1568:
1305:
252:
195:
273:
157:
1696:
Toxicological
Profile for Hexachlorobenzene (Update), US Dept of Health & Human Services, Sept 2002.
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1637:
Courtney, K.D. Hexachlorobenzene (HCB): A Review, Environmental
Research 1979; 20: p. 225-266.
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817:
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Persistent organic pollutants under the Convention on Long-Range Transboundary Air Pollution
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formerly used as a seed treatment, especially on wheat to control the fungal disease
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983:. Chronic oral exposure in humans has been shown to give rise to a liver disease (
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Hexachlorobenzene has been made on a laboratory scale since the 1890s, by the
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named it "dichloride of carbon" and claimed that the carbon was derived from
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420:
188:
844:, dwarf bunt. The compound was introduced in 1947, normally formulated as a
800:
reaction of chlorine with benzene or chlorobenzenes. A typical catalyst is
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972:
1690:. Ed. D. Sweet, US Dept. of Health & Human Services: Cincinnati, 2005.
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913: in this section. Unsourced material may be challenged and removed.
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741:), obtained a small sample of Julin's chloride of carbon to send to
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Except where otherwise noted, data are given for materials in their
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IARC Monographs on the Evaluation of Carcinogenic Risk to Humans
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Stockholm Convention on Persistent Organic Pollutants website
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Persistent organic pollutants under the Stockholm Convention
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207:
1536:
Marsella, John A.; et al., "Dimethylformamide",
1478:
1010:. It may cause long term adverse effects in the aquatic
769:
obtained hexachlorobenzene from the decomposition of
686:
Stockholm Convention on Persistent Organic Pollutants
1684:. World Health Organisation, Vol 79, 2001pp 493–567
691:
1507:. Vol. 26. Weinheim: Wiley-VCH. p. 558.
1680:International Agency for Research on Cancer. In:
1436:. Vol. 8. Weinheim: Wiley-VCH. p. 494.
1349:, Henry Bassett, J. Chem. Soc., 1867,20, 443-444
71:Perchlorobenzene; HCB; Julin's chloride of carbon
1725:
1688:Registry of Toxic Effects of Chemical Substances
1399:Cohen, Julius Berend; Hartley, Percival (1905).
1360:
838:(common bunt of wheat). It is also effective on
240:
1538:Kirk-Othmer Encyclopedia of Chemical Technology
425:228.83 °C (443.89 °F; 501.98 K)
92:
1504:Ullmann's Encyclopedia of Industrial Chemistry
1433:Ullmann's Encyclopedia of Industrial Chemistry
1546:10.1002/0471238961.0409130513011819.a01.pub2
1464:: CS1 maint: multiple names: authors list (
1398:
804:. Much milder reagents than chlorine (e.g.
725:synthesised the compound by the reaction of
318:InChI=1S/C6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9
1720:in the Pesticide Properties DataBase (PPDB)
1599:. The Carcinogenic Potency Database Project
1561:
1054:—different numbers of chlorine substituents
965:International Agency for Research on Cancer
871:Hexachlorobenzene can react violently with
328:InChI=1/C6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9
1342:
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1643:
1569:"Report on Carcinogens, Eleventh Edition"
1429:
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1080:
1078:
963:This material has been classified by the
929:Learn how and when to remove this message
260:
41:Ball-and-stick model of hexachlorobenzene
1618:http://www.nrdc.org/breastmilk/chem4.asp
1589:
1330:
1328:
1326:
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1322:
745:and Faraday for investigation. In 1867,
684:. It has been banned globally under the
1337:
701:, other chlorinated compounds (such as
289:
1726:
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1075:
1025:
435:325 °C (617 °F; 598 K)
189:
1319:
1230:CRC Handbook of Chemistry and Physics
1195:CRC Handbook of Chemistry and Physics
1160:CRC Handbook of Chemistry and Physics
1125:CRC Handbook of Chemistry and Physics
1090:CRC Handbook of Chemistry and Physics
948:Inhalation LC50 (rat): 3600 mg/m
848:but is now banned in many countries.
321:Key: CKAPSXZOOQJIBF-UHFFFAOYSA-N
156:
136:
31:Skeletal formula of hexachlorobenzene
1535:
1472:
1226:
1191:
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1086:
987:), skin lesions with discoloration,
911:adding citations to reliable sources
882:
820:can substitute for benzene as well.
1540:, New York: John Wiley, p. 6,
1279:
798:electrophilic aromatic substitution
331:Key: CKAPSXZOOQJIBF-UHFFFAOYAV
231:
215:
13:
945:Oral LD50 (mice): 4,000 mg/kg
942:Oral LD50 (rat): 10,000 mg/kg
818:the various hexachlorocyclohexanes
36:
26:
14:
1795:
1709:
1581:from the original on 2009-11-14.
1306:"RoC Profile: Hezachlorobenzene"
887:
777:vapours through a red-hot tube.
759:and the chlorine was from crude
692:Physical and chemical properties
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1479:Pesticide Properties Database.
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1022:in an aquatic species is high.
955:Hexachlorobenzene is an animal
898:needs additional citations for
638:(at 25 °C , 100 kPa).
1298:
1273:
1255:
1220:
1185:
1150:
1115:
828:Hexachlorobenzene was used in
373:
352:c1(Cl)c(Cl)c(Cl)c(Cl)c(Cl)c1Cl
1:
1483:. University of Hertfordshire
1347:On Julin's Chloride of Carbon
1063:
878:
863:, followed by acidic workup.
1227:Lide, David R., ed. (2009).
1192:Lide, David R., ed. (2009).
1157:Lide, David R., ed. (2009).
1122:Lide, David R., ed. (2009).
1087:Lide, David R., ed. (2009).
979:(renal tubular tumours) and
857:nucleophilically substitutes
780:
737:'s "perchloride of carbon" (
668:with the molecular formula C
7:
1313:National Toxicology Program
1045:
22:
10:
1800:
716:
1774:Suspected embryotoxicants
1759:IARC Group 2B carcinogens
866:
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21:
1754:Hazardous air pollutants
1513:10.1002/14356007.a19_313
1442:10.1002/14356007.o06_o03
1286:pubchem.ncbi.nlm.nih.gov
823:
405:White crystalline solid
1058:Pentachlorobenzenethiol
1036:porphyria cutanea tarda
985:porphyria cutanea tarda
859:hexachlorobenzene with
493:Magnetic susceptibility
832:to control the fungus
731:antimony pentachloride
664:and a six-substituted
42:
32:
1675:Additional references
1381:US patent 2792434
1362:US patent 2773104
1006:HCB is very toxic to
40:
30:
1769:Suspected teratogens
1744:Endocrine disruptors
1417:10.1039/CT9058701360
1405:J. Chem. Soc., Trans
907:improve this article
841:tilletia controversa
816:) also suffice, and
458:slightly soluble in
58:Preferred IUPAC name
1734:Obsolete pesticides
1597:"Hexachlorobenzene"
1481:"Hexachlorobenzene"
1282:"Hexachlorobenzene"
1235:Boca Raton, Florida
1200:Boca Raton, Florida
1165:Boca Raton, Florida
1130:Boca Raton, Florida
1095:Boca Raton, Florida
1026:Anatolian porphyria
969:Group 2B carcinogen
851:A minor industrial
814:chlorosulfonic acid
806:dichlorine monoxide
775:tetrachloroethylene
574:−127.6 kJ·mol
547:260.2 J·mol·K
523:201.2 J·mol·K
442:Solubility in water
397: g·mol
18:
1267:2014-04-16 at the
642:Infobox references
604:Related compounds
581:Enthalpy of fusion
470:; very soluble in
455:in other solvents
43:
33:
17:Hexachlorobenzene
16:
1717:Hexachlorobenzene
1460:cite encyclopedia
1248:978-1-4200-9084-0
1233:(90th ed.).
1213:978-1-4200-9084-0
1206:. p. 6-137.
1198:(90th ed.).
1178:978-1-4200-9084-0
1171:. p. 3-674.
1163:(90th ed.).
1143:978-1-4200-9084-0
1136:. p. 16-42.
1128:(90th ed.).
1108:978-1-4200-9084-0
1101:. p. 3-276.
1093:(90th ed.).
1008:aquatic organisms
939:
938:
931:
873:dimethylformamide
699:hydrochloric acid
654:Hexachlorobenzene
650:Chemical compound
648:
647:
619:Hexafluorobenzene
610:Related compounds
599:25.2 kJ·mol
499:−147.0·10 cm/mol
274:CompTox Dashboard
118:Interactive image
62:Hexachlorobenzene
47:
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1784:Perchlorocarbons
1702:, 11th Edition,
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993:photosensitivity
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743:Richard Phillips
739:Hexachloroethane
658:perchlorobenzene
623:Hexabromobenzene
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158:ChEMBL228514
77:Identifiers
69:Other names
1700:Merck Index
1069:Cited works
1012:environment
1001:breast milk
997:teratogenic
830:agriculture
723:Hugo Müller
402:Appearance
361:Properties
196:100.003.886
1749:Fungicides
1728:Categories
1603:2020-06-07
1487:2022-06-13
1291:2022-03-24
1064:References
989:ulceration
957:carcinogen
879:Toxicology
855:synthesis
771:chloroform
676:. It is a
468:chloroform
453:Solubility
447:insoluble
415:2.04 g/cm
390:Molar mass
262:4Z87H0LKUY
169:ChemSpider
138:CHEBI:5692
105:3D model (
84:CAS Number
1280:PubChem.
1239:CRC Press
1204:CRC Press
1169:CRC Press
1134:CRC Press
1099:CRC Press
861:alkoxides
781:Synthesis
761:saltpetre
757:cast iron
678:fungicide
556:formation
530:Std molar
1576:Archived
1265:Archived
1046:See also
1032:Anatolia
703:phosgene
660:, is an
495:(χ)
94:118-74-1
789:(the γ-
787:lindane
727:benzene
717:History
615:Benzene
532:entropy
472:benzene
460:ethanol
411:Density
229:PubChem
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977:kidney
867:Safety
810:iodine
791:isomer
709:, and
395:284.77
345:SMILES
217:C11042
149:ChEMBL
52:Names
1579:(PDF)
1572:(PDF)
1309:(PDF)
973:liver
824:Usage
656:, or
486:5.47
310:InChI
129:ChEBI
107:JSmol
1704:4600
1550:ISBN
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1466:link
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773:and
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253:UNII
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208:KEGG
178:8067
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