2270:
2121:
42:
2189:
2026:
575:
35:
985:
181:, which are of particular concern to human and environmental health, are produced in the high temperature environment of forest fires and have been found in the preserved ashes of lightning-ignited fires that predate synthetic dioxins. In addition, a variety of simple chlorinated hydrocarbons including
90:
with one or more hydrogens substituted by chlorine) includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of
1114:
Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006).
1032:, and causes reproductive problems (e.g., eggshell thinning) in certain bird species. DDT also posed further issues to the environment as it is extremely mobile, traces even being found in Antarctica despite the chemical never being used there. Some organochlorine compounds, such as
1051:
However, the presence of chlorine in an organic compound does not ensure toxicity. Some organochlorides are considered safe enough for consumption in foods and medicines. For example, peas and broad beans contain the natural chlorinated plant hormone
586:
Alkyl chlorides are versatile building blocks in organic chemistry. While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.
911:. Sodium ions leak through the nerve membrane and create a destabilizing negative "afterpotential" with hyperexcitability of the nerve. This leakage causes repeated discharges in the neuron either spontaneously or after a single stimulus.
212:, it is no longer a subject of research for potential therapeutic uses. The frogs obtain epibatidine through their diet which is then sequestered into their skin. Likely dietary sources are beetles, ants, mites, and flies.
471:
129:
due to the higher atomic weight of chlorine versus hydrogen. They have higher boiling and melting points compared to related hydrocarbons. Flammability reduces with increased chlorine substitution in hydrocarbons.
1379:
Elizabeth Norton Lasley (1999). "Having Their Toxins and Eating Them Too Study of the natural sources of many animals' chemical defenses is providing new insights into nature's medicine chest".
149:
Many organochlorine compounds have been isolated from natural sources ranging from bacteria to humans. Chlorinated organic compounds are found in nearly every class of biomolecules and
1060:(Splenda) is widely used in diet products. As of 2004, at least 165 organochlorides had been approved worldwide for use as pharmaceutical drugs, including the natural antibiotic
1016:
Some types of organochlorides have significant toxicity to plants or animals, including humans. Dioxins, produced when organic matter is burned in the presence of chlorine, are
232:
alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the
1000:(PCBs) were once commonly used electrical insulators and heat transfer agents. Their use has generally been phased out due to health concerns. PCBs were replaced by
753:
1677:
1117:
348:
Secondary and tertiary alcohols react with hydrogen chloride to give the corresponding chlorides. In the laboratory, the related reaction involving
1188:
1704:
362:
1024:). For example, DDT, which was widely used to control insects in the mid-20th century, also accumulates in food chains, as do its metabolites
1678:"The oxidation of chlorinated hydrocarbons" article from The Institute for Green Oxidation Chemistry at the Carnegie Mellon University website
942:(CNS) activity, followed by hyperexcitability, tremors, and then seizures. The mechanism of action is the insecticide binding at the
1153:
Claudia Wagner, Mustafa El Omari, Gabriele M. König (2009). "Biohalogenation: Nature's Way to
Synthesize Halogenated Metabolites".
1621:
Magnus, Volker; Ozga, Jocelyn A; Reinecke, Dennis M; Pierson, Gerald L; Larue, Thomas A; Cohen, Jerry D; Brenner, Mark L (1997).
17:
1556:
1452:
251:, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.
1480:"Mechanisms of toxic action and structure-activity relationships for organochlorine and synthetic pyrethroid insecticides"
1697:
1672:
565:
In the laboratory, thionyl chloride is especially convenient, because the byproducts are gaseous. Alternatively, the
1363:
1025:
92:
1682:
1690:
1134:
1029:
1001:
178:
825:
Several billion kilograms of chlorinated methanes are produced annually, mainly by chlorination of methane:
654:
are possible as well. In the presence of a strong base, alkyl chlorides undergo dehydrohalogenation to give
125:
modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than
1053:
1017:
481:
849:
The most important is dichloromethane, which is mainly used as a solvent. Chloromethane is a precursor to
254:
Chlorine adds to the multiple bonds on alkenes and alkynes as well, giving di- or tetra-chloro compounds.
1574:"Occurrence of 4-Cl-indoleacetic acid in broad beans and correlation of its levels with seed development"
1341:
233:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2224:
2219:
2214:
2209:
2204:
2194:
2137:
2031:
1952:
1947:
1804:
611:
2295:
1997:
1967:
1957:
1937:
1925:
1893:
1858:
1826:
1794:
1789:
1749:
1444:
900:
2402:
2340:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2300:
2285:
2275:
2126:
2101:
2096:
2081:
2066:
2046:
2041:
1992:
1920:
1903:
1853:
1848:
1843:
1838:
1774:
1764:
1728:
1631:
1233:
1204:
997:
773:. The annual production in 1985 was around 13 million tons, almost all of which was converted into
745:
501:
208:
effects and has stimulated research into new pain medication. However, because of its unacceptable
197:
in the environment is produced naturally by biological decomposition, forest fires, and volcanoes.
1020:
which pose dangers when they are released into the environment, as are some insecticides (such as
2290:
2280:
2091:
2076:
2061:
2051:
2036:
1977:
1962:
1942:
1932:
1913:
1908:
1898:
1888:
1831:
1799:
950:
2199:
2114:
2056:
2019:
2014:
2002:
1982:
1972:
1878:
1873:
1868:
1809:
1784:
1769:
1759:
1303:
Gribble, G. W. (1996). "Naturally occurring organohalogen compounds - A comprehensive survey".
939:
517:
2007:
1819:
1754:
1744:
1182:
904:
858:
122:
1673:"Formation of Chlorinated Hydrocarbons in Weathering Plant Material" article at SLAC website
1437:
2086:
2071:
1883:
1863:
1269:
635:
190:
1202:
Gordon W. Gribble (1999). "The diversity of naturally occurring organobromine compounds".
809:; they are therefore immiscible with water and effective in cleaning applications such as
8:
1987:
878:
802:
302:, hydrogen chloride instead of the more expensive chlorine is used for the same purpose:
103:
1273:
1598:
1573:
1504:
1479:
1337:
1645:
1622:
857:. Historically significant, but smaller in scale is chloroform, mainly a precursor to
1603:
1552:
1509:
1448:
1359:
1320:
1285:
1246:
1170:
1130:
969:
866:
806:
798:
774:
353:
263:
244:
209:
99:
1640:
1593:
1585:
1531:
1499:
1491:
1417:
1388:
1312:
1277:
1242:
1231:
Kjeld C. Engvild (1986). "Chlorine-Containing
Natural Compounds in Higher Plants".
1213:
1162:
1152:
1122:
1037:
794:
697:
670:
591:
493:
248:
134:
71:
1126:
1712:
1408:
1045:
1005:
786:
299:
182:
150:
107:
1392:
1089:
1033:
953:(GABA) chloride ionophore complex, which inhibits chloride flow into the nerve.
943:
908:
770:
749:
705:
701:
693:
682:
566:
2396:
2359:
1535:
674:
477:
349:
194:
138:
114:
are commonly used as solvents and are referred to as "chlorinated solvents".
75:
1607:
1289:
1174:
850:
814:
678:
639:
466:{\displaystyle {\ce {{R-OH}+HCl->{\overset {alkyl\ halide}{R-Cl}}+H2O}}}
267:
1513:
1324:
1260:
Gribble, G. W. (1994). "The
Natural production of chlorinated compounds".
1073:
977:
973:
884:
769:
The largest application of organochlorine chemistry is the production of
651:
266:(HCl) to give alkyl chlorides. For example, the industrial production of
201:
1589:
1495:
1316:
1281:
1077:
1069:
1065:
1061:
935:
927:
810:
790:
237:
186:
174:
162:
111:
50:
1421:
1166:
1217:
1057:
931:
892:
666:
619:
603:
391:
205:
166:
1572:
Pless, Tanja; Boettger, Michael; Hedden, Peter; Graebe, Jan (1984).
396:
41:
1041:
919:
854:
599:
492:
Alkyl chlorides are most easily prepared by treating alcohols with
271:
154:
79:
27:
Organic compound with at least 1 covalently bonded atom of chlorine
957:
748:
is rarely useful in chemical synthesis, but is a key step in the
647:
574:
225:
170:
158:
630:. Alkyl chlorides are substituted by softer halides such as the
1714:
1406:
965:
923:
915:
817:. They are mostly nonflammable or have very low flammability.
709:
686:
659:
655:
631:
87:
34:
1113:
961:
716:
643:
627:
623:
615:
607:
595:
337:
126:
785:
Most low molecular weight chlorinated hydrocarbons such as
713:
229:
907:, they prevent gate closure after activation and membrane
805:
are useful solvents. These solvents tend to be relatively
1659:
MDL Drug Data Report (MDDR), Elsevier MDL, version 2004.2
1620:
1571:
1021:
988:
Structure of mirex, a perchlorocarbon used as a pesticide
888:
456:
408:
984:
193:
have been isolated from marine algae. A majority of the
1378:
1623:"4-chloroindole-3-acetic and indole-3-acetic acids in
1435:
Jewkes, John; Sawers, David; Richard, Richard (1969).
1305:
Progress in the
Chemistry of Organic Natural Products
685:
reductively couples two alkyl halides to couple with
365:
1434:
204:, an alkaloid isolated from tree frogs, has potent
117:
1436:
1344:, Agency for Toxic Substances and Disease Registry
465:
257:
1443:(2nd ed.). New York: W. W. Norton. pp.
1372:
1201:
2394:
1230:
508:), but also commonly with sulfuryl chloride (SO
1528:Ullmann's Encyclopedia of Industrial Chemistry
1302:
1259:
1118:Ullmann's Encyclopedia of Industrial Chemistry
895:. Their mechanism of action differs slightly.
32:
1698:
1353:
938:. A 2- to 8-hour exposure leads to depressed
1187:: CS1 maint: multiple names: authors list (
869:which is used in the manufacture of Teflon.
487:
1546:
1705:
1691:
1076:(Lamictal), and the inhalation anesthetic
1004:(PBDEs), which bring similar toxicity and
1717:with other elements in the periodic table
1644:
1597:
1503:
1477:
1109:
1107:
1105:
980:, depending on their molecular structure.
1520:
1473:
1471:
1405:
1399:
1195:
1148:
1146:
983:
1347:
1338:Public Health Statement - Chloromethane
141:, which can result in cellular damage.
14:
2395:
1734:
1526:Robert L. Metcalf "Insect Control" in
1428:
1102:
883:The two main groups of organochlorine
1686:
1468:
1143:
622:. Alkyl chlorides readily react with
144:
91:profound environmental concern, with
2376:Academic research, no widespread use
1262:Environmental Science and Technology
891:-type compounds and the chlorinated
133:Aliphatic organochlorides are often
62:is concerned with the properties of
899:The DDT like compounds work on the
24:
879:Insecticide § Organochlorides
392:
25:
2414:
1666:
1551:. Blackwell Science. p. 68.
1547:Connell, D.; et al. (1999).
1484:Environmental Health Perspectives
820:
764:
95:being one of the most notorious.
2268:
2187:
2119:
2024:
1724:
914:Chlorinated cyclodienes include
573:
480:, this mixture was once used in
220:
118:Physical and chemical properties
40:
33:
1653:
1614:
1565:
1540:
1068:(Claritin), the antidepressant
759:
258:Reaction with hydrogen chloride
1331:
1296:
1253:
1224:
1056:(4-Cl-IAA); and the sweetener
1002:polybrominated diphenyl ethers
692:Some organochlorides (such as
598:gives alcohols. Reaction with
215:
13:
1:
1646:10.1016/S0031-9422(97)00229-X
1549:Introduction to Ecotoxicology
1127:10.1002/14356007.a06_233.pub2
1095:
1072:(Zoloft), the anti-epileptic
1018:persistent organic pollutants
992:
872:
1530:Wiley-VCH, Wienheim, 2002.
1247:10.1016/0031-9422(86)80002-4
1115:"Chlorinated Hydrocarbons".
1054:4-chloroindole-3-acetic acid
581:
482:qualitative organic analysis
270:proceeds by the reaction of
7:
1393:10.1525/bisi.1999.49.12.945
1342:Centers for Disease Control
1083:
1011:
780:
665:Alkyl chlorides react with
590:Heating alkyl halides with
234:Friedel-Crafts halogenation
200:The natural organochloride
29:
10:
2419:
876:
752:of several organochlorine
612:Williamson ether synthesis
484:for classifying alcohols.
2351:
2265:
2184:
1736:
1732:
1722:
998:Polychlorinated biphenyls
901:peripheral nervous system
488:Other chlorinating agents
137:as chlorine can act as a
1536:10.1002/14356007.a14_263
1439:The sources of invention
1205:Chemical Society Reviews
746:Reductive dechlorination
502:phosphorus pentachloride
98:Organochlorides such as
74:containing at least one
64:organochlorine compounds
60:Organochlorine chemistry
1478:J R Coats (July 1990).
1121:. Weinheim: Wiley-VCH.
1048:due to their toxicity.
972:. These can be either
956:Other examples include
951:gamma-aminobutyric acid
236:, using chlorine and a
49:Two representations of
18:Organochlorine compound
2371:Many uses in chemistry
2366:Core organic chemistry
1354:Schwarcz, Joe (2012).
989:
940:central nervous system
638:. Reaction with other
518:phosphorus trichloride
467:
413:
987:
859:chlorodifluoromethane
754:persistent pollutants
468:
387:
247:, using chlorine and
1064:, the antihistamine
636:Finkelstein reaction
626:to give substituted
363:
191:carbon tetrachloride
1590:10.1104/pp.74.2.320
1496:10.1289/ehp.9087255
1356:The Right Chemistry
1317:10.1021/np50088a001
1282:10.1021/es00056a712
1274:1994EnST...28..310G
1044:, are even used as
803:tetrachloroethylene
458:
412:
410:
395:
262:Alkenes react with
104:tetrachloroethylene
990:
704:was produced from
673:, transforming an
463:
446:
398:
145:Natural occurrence
2390:
2389:
2346:
2345:
1558:978-0-632-03852-7
1454:978-0-393-00502-8
1422:10.1021/om030621b
1416:(25): 5154–5178.
1167:10.1021/np800651m
1038:nitrogen mustards
970:pentachlorophenol
903:. At the axon's
867:tetrafluoroethene
799:trichloroethylene
775:polyvinylchloride
698:alkylating agents
696:) may be used as
671:Grignard reagents
461:
449:
441:
439:
436:
433:
428:
420:
401:
385:
378:
370:
354:hydrochloric acid
264:hydrogen chloride
245:haloform reaction
210:therapeutic index
135:alkylating agents
100:trichloroethylene
76:covalently bonded
72:organic compounds
57:
56:
16:(Redirected from
2410:
2382:
2377:
2372:
2367:
2272:
2271:
2191:
2190:
2123:
2122:
2028:
2027:
1725:
1707:
1700:
1693:
1684:
1683:
1660:
1657:
1651:
1650:
1648:
1618:
1612:
1611:
1601:
1578:Plant Physiology
1569:
1563:
1562:
1544:
1538:
1524:
1518:
1517:
1507:
1475:
1466:
1465:
1463:
1461:
1442:
1432:
1426:
1425:
1403:
1397:
1396:
1376:
1370:
1369:
1358:. Random House.
1351:
1345:
1335:
1329:
1328:
1300:
1294:
1293:
1268:(7): 310A–319A.
1257:
1251:
1250:
1228:
1222:
1221:
1218:10.1039/a900201d
1199:
1193:
1192:
1186:
1178:
1150:
1141:
1140:
1111:
1046:chemical weapons
795:dichloroethylene
677:compound into a
614:; reaction with
592:sodium hydroxide
577:
494:thionyl chloride
472:
470:
469:
464:
462:
459:
457:
454:
447:
442:
440:
437:
434:
431:
429:
426:
425:
418:
416:
414:
411:
409:
406:
399:
383:
379:
376:
375:
368:
352:in concentrated
323:
322:
318:
249:sodium hydroxide
151:natural products
44:
37:
30:
21:
2418:
2417:
2413:
2412:
2411:
2409:
2408:
2407:
2403:Organochlorides
2393:
2392:
2391:
2386:
2385:
2380:
2375:
2370:
2365:
2347:
2269:
2188:
2120:
2025:
1718:
1711:
1669:
1664:
1663:
1658:
1654:
1619:
1615:
1570:
1566:
1559:
1545:
1541:
1525:
1521:
1476:
1469:
1459:
1457:
1455:
1433:
1429:
1409:Organometallics
1404:
1400:
1387:(12): 945–950.
1377:
1373:
1366:
1352:
1348:
1336:
1332:
1301:
1297:
1258:
1254:
1241:(4): 7891–791.
1229:
1225:
1200:
1196:
1180:
1179:
1151:
1144:
1137:
1112:
1103:
1098:
1086:
1034:sulfur mustards
1014:
1006:bioaccumulation
995:
947:
881:
875:
864:
844:
840:
836:
832:
823:
787:dichloromethane
783:
767:
762:
743:
742:+ 4 NaCl + 3 Pb
741:
737:
733:
729:
725:
584:
560:
556:
550:
546:
542:
535:
531:
523:
515:
511:
507:
499:
490:
455:
450:
430:
421:
417:
415:
407:
402:
397:
386:
371:
367:
366:
364:
361:
360:
341:
335:
331:
327:
320:
316:
315:
313:
309:
300:oxychlorination
293:
289:
285:
281:
260:
223:
218:
183:dichloromethane
147:
120:
108:dichloromethane
68:organochlorides
39:
38:
28:
23:
22:
15:
12:
11:
5:
2416:
2406:
2405:
2388:
2387:
2384:
2383:
2378:
2373:
2368:
2363:
2360:Chemical bonds
2356:
2355:
2353:
2349:
2348:
2344:
2343:
2338:
2333:
2328:
2323:
2318:
2313:
2308:
2303:
2298:
2293:
2288:
2283:
2278:
2273:
2266:
2263:
2262:
2257:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2202:
2197:
2192:
2185:
2182:
2181:
2177:
2176:
2173:
2170:
2167:
2164:
2161:
2158:
2155:
2152:
2149:
2146:
2143:
2140:
2135:
2132:
2129:
2124:
2117:
2112:
2108:
2107:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2022:
2017:
2011:
2010:
2005:
2000:
1995:
1990:
1985:
1980:
1975:
1970:
1965:
1960:
1955:
1950:
1945:
1940:
1935:
1930:
1928:
1923:
1917:
1916:
1911:
1906:
1901:
1896:
1891:
1886:
1881:
1876:
1871:
1866:
1861:
1856:
1851:
1846:
1841:
1836:
1834:
1829:
1823:
1822:
1817:
1812:
1807:
1802:
1797:
1792:
1787:
1781:
1780:
1777:
1772:
1767:
1762:
1757:
1752:
1747:
1741:
1740:
1737:
1735:
1733:
1731:
1723:
1720:
1719:
1710:
1709:
1702:
1695:
1687:
1681:
1680:
1675:
1668:
1667:External links
1665:
1662:
1661:
1652:
1639:(4): 675–681.
1632:Phytochemistry
1613:
1564:
1557:
1539:
1519:
1467:
1453:
1427:
1398:
1371:
1364:
1346:
1330:
1295:
1252:
1234:Phytochemistry
1223:
1212:(5): 335–346.
1194:
1161:(3): 540–553.
1142:
1135:
1100:
1099:
1097:
1094:
1093:
1092:
1090:Organic halide
1085:
1082:
1013:
1010:
994:
991:
982:
981:
954:
945:
912:
909:depolarization
905:sodium channel
874:
871:
862:
847:
846:
842:
838:
834:
830:
822:
821:Chloromethanes
819:
782:
779:
771:vinyl chloride
766:
765:Vinyl chloride
763:
761:
758:
750:biodegradation
739:
735:
731:
727:
723:
721:
706:ethyl chloride
702:Tetraethyllead
694:ethyl chloride
683:Wurtz reaction
681:compound. The
583:
580:
579:
578:
567:Appel reaction
563:
562:
558:
554:
551:
548:
544:
540:
537:
533:
529:
521:
513:
509:
505:
497:
489:
486:
474:
473:
453:
445:
424:
405:
394:
390:
382:
374:
346:
345:
339:
333:
329:
325:
311:
307:
296:
295:
291:
287:
283:
279:
259:
256:
222:
219:
217:
214:
146:
143:
119:
116:
55:
54:
46:
45:
26:
9:
6:
4:
3:
2:
2415:
2404:
2401:
2400:
2398:
2379:
2374:
2369:
2364:
2361:
2358:
2357:
2354:
2350:
2342:
2339:
2337:
2334:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2312:
2309:
2307:
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2267:
2264:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2243:
2241:
2238:
2236:
2233:
2231:
2228:
2226:
2223:
2221:
2218:
2216:
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2186:
2183:
2179:
2178:
2174:
2171:
2168:
2165:
2162:
2159:
2156:
2153:
2150:
2147:
2144:
2141:
2139:
2136:
2133:
2130:
2128:
2125:
2118:
2116:
2113:
2110:
2109:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2030:
2023:
2021:
2018:
2016:
2013:
2012:
2009:
2006:
2004:
2001:
1999:
1996:
1994:
1991:
1989:
1986:
1984:
1981:
1979:
1976:
1974:
1971:
1969:
1966:
1964:
1961:
1959:
1956:
1954:
1951:
1949:
1946:
1944:
1941:
1939:
1936:
1934:
1931:
1929:
1927:
1924:
1922:
1919:
1918:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1895:
1892:
1890:
1887:
1885:
1882:
1880:
1877:
1875:
1872:
1870:
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1850:
1847:
1845:
1842:
1840:
1837:
1835:
1833:
1830:
1828:
1825:
1824:
1821:
1818:
1816:
1813:
1811:
1808:
1806:
1803:
1801:
1798:
1796:
1793:
1791:
1788:
1786:
1783:
1782:
1778:
1776:
1773:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1746:
1743:
1742:
1738:
1730:
1727:
1726:
1721:
1716:
1713:Compounds of
1708:
1703:
1701:
1696:
1694:
1689:
1688:
1685:
1679:
1676:
1674:
1671:
1670:
1656:
1647:
1642:
1638:
1634:
1633:
1628:
1626:
1625:Pisum sativum
1617:
1609:
1605:
1600:
1595:
1591:
1587:
1583:
1579:
1575:
1568:
1560:
1554:
1550:
1543:
1537:
1533:
1529:
1523:
1515:
1511:
1506:
1501:
1497:
1493:
1489:
1485:
1481:
1474:
1472:
1456:
1450:
1446:
1441:
1440:
1431:
1423:
1419:
1415:
1411:
1410:
1402:
1394:
1390:
1386:
1382:
1375:
1367:
1365:9780385671606
1361:
1357:
1350:
1343:
1339:
1334:
1326:
1322:
1318:
1314:
1311:(10): 1–423.
1310:
1306:
1299:
1291:
1287:
1283:
1279:
1275:
1271:
1267:
1263:
1256:
1248:
1244:
1240:
1236:
1235:
1227:
1219:
1215:
1211:
1207:
1206:
1198:
1190:
1184:
1176:
1172:
1168:
1164:
1160:
1156:
1149:
1147:
1138:
1132:
1128:
1124:
1120:
1119:
1110:
1108:
1106:
1101:
1091:
1088:
1087:
1081:
1079:
1075:
1071:
1067:
1063:
1059:
1055:
1049:
1047:
1043:
1039:
1035:
1031:
1027:
1023:
1019:
1009:
1007:
1003:
999:
986:
979:
975:
971:
967:
963:
959:
955:
952:
948:
941:
937:
933:
929:
925:
921:
917:
913:
910:
906:
902:
898:
897:
896:
894:
890:
886:
880:
870:
868:
860:
856:
852:
851:chlorosilanes
828:
827:
826:
818:
816:
812:
808:
804:
800:
796:
792:
788:
778:
776:
772:
757:
755:
751:
747:
722:4 NaPb + 4 CH
720:
718:
715:
711:
707:
703:
699:
695:
690:
688:
684:
680:
676:
675:electrophilic
672:
668:
663:
661:
657:
653:
649:
645:
641:
640:pseudohalides
637:
633:
629:
625:
621:
617:
613:
609:
605:
601:
597:
593:
588:
576:
572:
571:
570:
569:can be used:
568:
552:
538:
527:
526:
525:
519:
503:
495:
485:
483:
479:
478:Lucas reagent
451:
443:
422:
403:
388:
380:
372:
359:
358:
357:
355:
351:
350:zinc chloride
343:
305:
304:
303:
301:
277:
276:
275:
273:
269:
265:
255:
252:
250:
246:
241:
239:
235:
231:
227:
221:From chlorine
213:
211:
207:
203:
198:
196:
195:chloromethane
192:
188:
184:
180:
176:
172:
168:
164:
160:
156:
152:
142:
140:
139:leaving group
136:
131:
128:
124:
115:
113:
109:
105:
101:
96:
94:
89:
85:
81:
77:
73:
69:
65:
61:
52:
48:
47:
43:
36:
31:
19:
2381:Bond unknown
1814:
1655:
1636:
1630:
1624:
1616:
1584:(2): 320–3.
1581:
1577:
1567:
1548:
1542:
1527:
1522:
1487:
1483:
1458:. Retrieved
1438:
1430:
1413:
1407:
1401:
1384:
1380:
1374:
1355:
1349:
1333:
1308:
1304:
1298:
1265:
1261:
1255:
1238:
1232:
1226:
1209:
1203:
1197:
1183:cite journal
1158:
1155:J. Nat. Prod
1154:
1116:
1050:
1015:
996:
949:site in the
885:insecticides
882:
848:
824:
815:dry cleaning
784:
768:
760:Applications
744:
691:
679:nucleophilic
664:
589:
585:
564:
557:→ RCl + POCl
491:
475:
347:
297:
268:chloroethane
261:
253:
242:
224:
199:
148:
132:
123:Chlorination
121:
97:
84:chloroalkane
83:
67:
63:
59:
58:
1490:: 255–262.
1074:lamotrigine
1008:concerns.
978:hydrophobic
974:hydrophilic
652:thiocyanate
543:→ 3 RCl + H
539:3 ROH + PCl
476:Called the
216:Preparation
202:epibatidine
175:fatty acids
163:amino acids
1381:BioScience
1136:3527306730
1096:References
1078:isoflurane
1070:sertraline
1066:loratadine
1062:vancomycin
993:Insulators
936:endosulfan
928:heptachlor
893:alicyclics
877:See also:
873:Pesticides
811:degreasing
791:chloroform
730:Cl → Pb(CH
620:thioethers
604:aryloxides
532:→ RCl + SO
528:ROH + SOCl
314:+ 2 HCl +
286:+ HCl → CH
274:with HCl:
240:catalyst.
238:Lewis acid
187:chloroform
167:flavonoids
153:including
112:chloroform
51:chloroform
2362:to carbon
1058:sucralose
932:chlordane
855:silicones
807:non-polar
667:magnesium
600:alkoxides
582:Reactions
553:ROH + PCl
423:−
393:Δ
373:−
206:analgesic
155:alkaloids
2397:Category
1608:16663416
1290:22662801
1175:19245259
1084:See also
1042:Lewisite
1012:Toxicity
920:dieldrin
887:are the
781:Solvents
669:to give
642:such as
389:→
272:ethylene
171:steroids
159:terpenes
80:chlorine
78:atom of
2180:
1599:1066676
1514:2176589
1505:1567810
1460:11 July
1325:8795309
1270:Bibcode
958:dicofol
845:+ x HCl
777:(PVC).
660:alkynes
656:alkenes
648:cyanide
634:in the
610:in the
319:⁄
226:Alkanes
179:Dioxins
88:alkanes
86:class (
2352:Legend
1715:carbon
1606:
1596:
1555:
1512:
1502:
1451:
1447:–237.
1362:
1323:
1288:
1173:
1133:
1040:, and
968:, and
966:kepone
924:endrin
916:aldrin
865:) and
861:(CHClF
833:+ x Cl
710:sodium
708:and a
687:sodium
650:, and
632:iodide
628:amines
624:amines
616:thiols
608:ethers
516:) and
438:halide
435:
328:→ ClCH
189:, and
173:, and
82:. The
962:mirex
717:alloy
644:azide
618:give
606:give
596:water
561:+ HCl
536:+ HCl
500:) or
496:(SOCl
432:alkyl
336:Cl +
127:water
66:, or
1604:PMID
1553:ISBN
1510:PMID
1462:2018
1449:ISBN
1360:ISBN
1321:PMID
1286:PMID
1189:link
1171:PMID
1131:ISBN
1028:and
944:GABA
934:and
853:and
837:→ CH
813:and
801:and
714:lead
520:(PCl
504:(PCl
400:ZnCl
282:C=CH
243:The
230:aryl
228:and
110:and
93:TCDD
2326:CEs
2321:CCf
2316:CBk
2311:CCm
2306:CAm
2301:CPu
2296:CNp
2286:CPa
2281:CTh
2260:CYb
2255:CTm
2250:CEr
2245:CHo
2240:CDy
2235:CTb
2230:CGd
2225:CEu
2220:CSm
2215:CPm
2210:CNd
2205:CPr
2200:CCe
2195:CLa
2175:Og
2172:Ts
2169:Lv
2166:Mc
2163:Fl
2160:Nh
2157:Cn
2154:Rg
2151:Ds
2148:Mt
2145:Hs
2142:Bh
2138:CSg
2134:Db
2131:Rf
2115:CRa
2111:Fr
2106:Rn
2102:CAt
2097:CPo
2092:CBi
2087:CPb
2082:CTl
2077:CHg
2072:CAu
2067:CPt
2062:CIr
2057:COs
2052:CRe
2042:CTa
2037:CHf
2032:CLu
2020:CBa
2015:CCs
2008:CXe
1998:CTe
1993:CSb
1988:CSn
1983:CIn
1978:CCd
1973:CAg
1968:CPd
1963:CRh
1958:CRu
1953:CTc
1948:CMo
1943:CNb
1938:CZr
1926:CSr
1921:CRb
1914:CKr
1909:CBr
1904:CSe
1899:CAs
1894:CGe
1889:CGa
1884:CZn
1879:CCu
1874:CNi
1869:CCo
1864:CFe
1859:CMn
1854:CCr
1844:CTi
1839:CSc
1832:CCa
1820:CAr
1815:CCl
1800:CSi
1795:CAl
1790:CMg
1785:CNa
1779:Ne
1750:CBe
1745:CLi
1739:He
1641:doi
1594:PMC
1586:doi
1532:doi
1500:PMC
1492:doi
1445:235
1418:doi
1389:doi
1313:doi
1278:doi
1243:doi
1214:doi
1163:doi
1123:doi
1030:DDD
1026:DDE
1022:DDT
976:or
889:DDT
839:4−x
658:or
602:or
594:or
524:):
384:HCl
310:=CH
298:In
2399::
2341:No
2336:Md
2331:Fm
2291:CU
2276:Ac
2127:Lr
2047:CW
2003:CI
1933:CY
1849:CV
1827:CK
1810:CS
1805:CP
1775:CF
1770:CO
1765:CN
1760:CC
1755:CB
1729:CH
1637:46
1635:.
1629:.
1602:.
1592:.
1582:74
1580:.
1576:.
1508:.
1498:.
1488:87
1486:.
1482:.
1470:^
1414:22
1412:.
1385:45
1383:.
1340:,
1319:.
1309:68
1307:.
1284:.
1276:.
1266:28
1264:.
1239:25
1237:.
1210:28
1208:.
1185:}}
1181:{{
1169:.
1159:72
1157:.
1145:^
1129:.
1104:^
1080:.
1036:,
964:,
960:,
930:,
926:,
922:,
918:,
841:Cl
829:CH
797:,
793:,
789:,
756:.
734:CH
726:CH
719::
700:.
689:.
662:.
646:,
547:PO
512:Cl
427:Cl
377:OH
356::
332:CH
306:CH
294:Cl
290:CH
185:,
177:.
169:,
165:,
161:,
157:,
106:,
102:,
70:,
53:.
1706:e
1699:t
1692:v
1649:.
1643::
1627:"
1610:.
1588::
1561:.
1534::
1516:.
1494::
1464:.
1424:.
1420::
1395:.
1391::
1368:.
1327:.
1315::
1292:.
1280::
1272::
1249:.
1245::
1220:.
1216::
1191:)
1177:.
1165::
1139:.
1125::
946:A
863:2
843:x
835:2
831:4
740:4
738:)
736:2
732:3
728:2
724:3
712:–
559:3
555:5
549:3
545:3
541:3
534:2
530:2
522:3
514:2
510:2
506:5
498:2
460:O
452:2
448:H
444:+
419:R
404:2
381:+
369:R
344:.
342:O
340:2
338:H
334:2
330:2
326:2
324:O
321:2
317:1
312:2
308:2
292:2
288:3
284:2
280:2
278:H
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
