2237:
2088:
2156:
1993:
31:
564:
24:
952:
170:, 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
79:
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
1081:
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).
999:, 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
1018:
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
575:
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.
878:. 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.
201:, 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.
460:
118:
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.
1346:
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".
138:
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
1027:(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
983:
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
221:
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
1084:
1155:
967:(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
1671:
1644:
337:
Secondary and tertiary alcohols react with hydrogen chloride to give the corresponding chlorides. In the laboratory, the related reaction involving
351:
991:). For example, DDT, which was widely used to control insects in the mid-20th century, also accumulates in food chains, as do its metabolites
1645:"The oxidation of chlorinated hydrocarbons" article from The Institute for Green Oxidation Chemistry at the Carnegie Mellon University website
1523:
1419:
1664:
909:(CNS) activity, followed by hyperexcitability, tremors, and then seizures. The mechanism of action is the insecticide binding at the
1330:
1120:
Claudia Wagner, Mustafa El Omari, Gabriele M. König (2009). "Biohalogenation: Nature's Way to
Synthesize Halogenated Metabolites".
1588:
Magnus, Volker; Ozga, Jocelyn A; Reinecke, Dennis M; Pierson, Gerald L; Larue, Thomas A; Cohen, Jerry D; Brenner, Mark L (1997).
992:
81:
685:) may be used as alkylating agents in production of alkyl compounds. In the case of ethyl chloride, which was used to produce
1657:
1101:
996:
968:
167:
240:, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.
1447:"Mechanisms of toxic action and structure-activity relationships for organochlorine and synthetic pyrethroid insecticides"
1639:
1020:
984:
470:
1308:
554:
In the laboratory, thionyl chloride is especially convenient, because the byproducts are gaseous. Alternatively, the
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917:
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Several billion kilograms of chlorinated methanes are produced annually, mainly by chlorination of methane:
643:
are possible as well. In the presence of a strong base, alkyl chlorides undergo dehydrohalogenation to give
114:
modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than
1736:
1726:
2166:
2081:
2023:
1986:
1981:
1969:
1949:
1939:
1845:
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1835:
1776:
1751:
906:
816:
The most important is dichloromethane, which is mainly used as a solvent. Chloromethane is a precursor to
506:
243:
Chlorine adds to the multiple bonds on alkenes and alkynes as well, giving di- or tetra-chloro compounds.
1541:"Occurrence of 4-Cl-indoleacetic acid in broad beans and correlation of its levels with seed development"
1974:
1786:
1721:
1711:
1149:
825:
111:
2053:
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1954:
769:
740:. The annual production in 1985 was around 13 million tons, almost all of which was converted into
197:
effects and has stimulated research into new pain medication. However, because of its unacceptable
186:
in the environment is produced naturally by biological decomposition, forest fires, and volcanoes.
92:
987:
which pose dangers when they are released into the environment, as are some insecticides (such as
1270:
Gribble, G. W. (1996). "Naturally occurring organohalogen compounds - A comprehensive survey".
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1640:"Formation of Chlorinated Hydrocarbons in Weathering Plant Material" article at SLAC website
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1169:
Gordon W. Gribble (1999). "The diversity of naturally occurring organobromine compounds".
1012:
972:
776:; they are therefore immiscible with water and effective in cleaning applications such as
753:
288:
171:
139:
96:
291:, hydrogen chloride instead of the more expensive chlorine is used for the same purpose:
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824:. Historically significant, but smaller in scale is chloroform, mainly a precursor to
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2326:
1213:
663:
466:
338:
183:
127:
64:
1198:
Kjeld C. Engvild (1986). "Chlorine-Containing
Natural Compounds in Higher Plants".
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667:
628:
256:
1093:
1359:
1040:
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30:
920:(GABA) chloride ionophore complex, which inhibits chloride flow into the nerve.
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1028:
902:
894:
777:
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100:
39:
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103:
are commonly used as solvents and are referred to as "chlorinated solvents".
1024:
898:
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608:
592:
563:
194:
155:
1574:
1256:
1141:
455:{\displaystyle {\ce {{R-OH}+HCl->{\overset {alkyl\ halide}{R-Cl}}+H2O}}}
1480:
1291:
1227:
Gribble, G. W. (1994). "The
Natural production of chlorinated compounds".
1008:
886:
821:
736:
The largest application of organochlorine chemistry is the production of
588:
260:
255:(HCl) to give alkyl chlorides. For example, the industrial production of
143:
68:
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23:
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380:
76:
1539:
Pless, Tanja; Boettger, Michael; Hedden, Peter; Graebe, Jan (1984).
385:
481:
Alkyl chlorides are most easily prepared by treating alcohols with
16:
Organic compound with at least 1 covalently bonded atom of chlorine
950:
928:
697:
632:
616:
612:
604:
596:
584:
326:
115:
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694:
619:. Alkyl chlorides are substituted by softer halides such as the
218:
1653:
1373:
784:. They are mostly nonflammable or have very low flammability.
988:
855:
752:
Most low molecular weight chlorinated hydrocarbons such as
874:, they prevent gate closure after activation and membrane
772:
are useful solvents. These solvents tend to be relatively
1626:
MDL Drug Data Report (MDDR), Elsevier MDL, version 2004.2
955:
Structure of mirex, a perchlorocarbon used as a pesticide
445:
397:
182:
have been isolated from marine algae. A majority of the
1590:"4-chloroindole-3-acetic and indole-3-acetic acids in
1402:
Jewkes, John; Sawers, David; Richard, Richard (1969).
1272:
Progress in the
Chemistry of Organic Natural Products
674:
reductively couples two alkyl halides to couple with
354:
18:
2318:
193:, an alkaloid isolated from tree frogs, has potent
1403:
1311:, Agency for Toxic Substances and Disease Registry
454:
1410:(2nd ed.). New York: W. W. Norton. pp.
497:), but also commonly with sulfuryl chloride (SO
1495:Ullmann's Encyclopedia of Industrial Chemistry
1085:Ullmann's Encyclopedia of Industrial Chemistry
862:. Their mechanism of action differs slightly.
21:
1665:
905:. A 2- to 8-hour exposure leads to depressed
8:
1154:: CS1 maint: multiple names: authors list (
836:which is used in the manufacture of Teflon.
1672:
1658:
1650:
1043:(Lamictal), and the inhalation anesthetic
971:(PBDEs), which bring similar toxicity and
1684:with other elements in the periodic table
1611:
1564:
1470:
1076:
1074:
1072:
947:, depending on their molecular structure.
444:
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356:
355:
353:
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1438:
1115:
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1305:Public Health Statement - Chloromethane
1068:
130:, which can result in cellular damage.
1701:
1493:Robert L. Metcalf "Insect Control" in
1147:
850:The two main groups of organochlorine
611:. Alkyl chlorides readily react with
80:profound environmental concern, with
7:
2343:Academic research, no widespread use
1229:Environmental Science and Technology
858:-type compounds and the chlorinated
122:Aliphatic organochlorides are often
51:is concerned with the properties of
866:The DDT like compounds work on the
846:Insecticide § Organochlorides
381:
14:
1518:. Blackwell Science. p. 68.
1514:Connell, D.; et al. (1999).
1451:Environmental Health Perspectives
84:being one of the most notorious.
2235:
2154:
2086:
1991:
1691:
881:Chlorinated cyclodienes include
562:
469:, this mixture was once used in
107:Physical and chemical properties
29:
22:
1035:(Claritin), the antidepressant
247:Reaction with hydrogen chloride
1023:(4-Cl-IAA); and the sweetener
969:polybrominated diphenyl ethers
681:Some organochlorides (such as
587:gives alcohols. Reaction with
1:
1613:10.1016/S0031-9422(97)00229-X
1516:Introduction to Ecotoxicology
1094:10.1002/14356007.a06_233.pub2
1039:(Zoloft), the anti-epileptic
985:persistent organic pollutants
1497:Wiley-VCH, Wienheim, 2002.
1214:10.1016/0031-9422(86)80002-4
1082:"Chlorinated Hydrocarbons".
1021:4-chloroindole-3-acetic acid
471:qualitative organic analysis
259:proceeds by the reaction of
1360:10.1525/bisi.1999.49.12.945
1309:Centers for Disease Control
654:Alkyl chlorides react with
579:Heating alkyl halides with
223:Friedel-Crafts halogenation
189:The natural organochloride
2386:
843:
601:Williamson ether synthesis
473:for classifying alcohols.
2232:
2151:
1703:
1699:
1689:
965:Polychlorinated biphenyls
868:peripheral nervous system
477:Other chlorinating agents
126:as chlorine can act as a
1503:10.1002/14356007.a14_263
1406:The sources of invention
1172:Chemical Society Reviews
491:phosphorus pentachloride
87:Organochlorides such as
63:containing at least one
53:organochlorine compounds
49:Organochlorine chemistry
1445:J R Coats (July 1990).
1088:. Weinheim: Wiley-VCH.
1015:due to their toxicity.
939:. These can be either
923:Other examples include
918:gamma-aminobutyric acid
689:, it is reacted with a
225:, using chlorine and a
38:Two representations of
2338:Many uses in chemistry
2333:Core organic chemistry
1321:Schwarcz, Joe (2012).
956:
907:central nervous system
627:. Reaction with other
507:phosphorus trichloride
456:
402:
954:
826:chlorodifluoromethane
457:
376:
236:, using chlorine and
1031:, the antihistamine
625:Finkelstein reaction
615:to give substituted
352:
180:carbon tetrachloride
1557:10.1104/pp.74.2.320
1463:10.1289/ehp.9087255
1323:The Right Chemistry
1284:10.1021/np50088a001
1249:10.1021/es00056a712
1241:1994EnST...28..310G
1011:, are even used as
770:tetrachloroethylene
447:
401:
399:
384:
251:Alkenes react with
93:tetrachloroethylene
957:
662:, transforming an
452:
435:
387:
134:Natural occurrence
2357:
2356:
2313:
2312:
1525:978-0-632-03852-7
1421:978-0-393-00502-8
1389:10.1021/om030621b
1383:(25): 5154–5178.
1134:10.1021/np800651m
1005:nitrogen mustards
937:pentachlorophenol
870:. At the axon's
834:tetrafluoroethene
766:trichloroethylene
742:polyvinylchloride
660:Grignard reagents
450:
438:
430:
428:
425:
422:
417:
409:
390:
374:
367:
359:
343:hydrochloric acid
253:hydrogen chloride
234:haloform reaction
199:therapeutic index
124:alkylating agents
89:trichloroethylene
65:covalently bonded
61:organic compounds
46:
45:
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2349:
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1545:Plant Physiology
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1325:. Random House.
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1260:
1235:(7): 310A–319A.
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1185:10.1039/a900201d
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1145:
1117:
1108:
1107:
1078:
1013:chemical weapons
762:dichloroethylene
666:compound into a
603:; reaction with
581:sodium hydroxide
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483:thionyl chloride
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238:sodium hydroxide
140:natural products
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2370:Organochlorides
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1376:Organometallics
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1354:(12): 945–950.
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1001:sulfur mustards
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973:bioaccumulation
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831:
811:
807:
803:
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754:dichloromethane
750:
734:
729:
724:
723:+ 4 NaCl + 3 Pb
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97:dichloromethane
57:organochlorides
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1634:External links
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1606:(4): 675–681.
1599:Phytochemistry
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1201:Phytochemistry
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1179:(5): 335–346.
1161:
1128:(3): 540–553.
1109:
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1057:Organic halide
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876:depolarization
872:sodium channel
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813:
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788:Chloromethanes
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749:
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738:vinyl chloride
733:
732:Vinyl chloride
730:
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720:
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712:
708:
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702:
687:tetraethyllead
683:ethyl chloride
672:Wurtz reaction
670:compound. The
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556:Appel reaction
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135:
132:
108:
105:
44:
43:
35:
34:
15:
13:
10:
9:
6:
4:
3:
2:
2382:
2371:
2368:
2367:
2365:
2346:
2341:
2336:
2331:
2328:
2325:
2324:
2321:
2317:
2309:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2234:
2231:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2153:
2150:
2146:
2145:
2141:
2138:
2135:
2132:
2129:
2126:
2123:
2120:
2117:
2114:
2111:
2108:
2106:
2103:
2100:
2097:
2095:
2092:
2085:
2083:
2080:
2077:
2076:
2072:
2070:
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2042:
2040:
2037:
2035:
2032:
2030:
2027:
2025:
2022:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2002:
2000:
1997:
1990:
1988:
1985:
1983:
1980:
1979:
1976:
1973:
1971:
1968:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1946:
1943:
1941:
1938:
1936:
1933:
1931:
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1898:
1896:
1894:
1891:
1889:
1886:
1885:
1882:
1879:
1877:
1874:
1872:
1869:
1867:
1864:
1862:
1859:
1857:
1854:
1852:
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1812:
1809:
1807:
1804:
1802:
1800:
1797:
1795:
1792:
1791:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1765:
1763:
1760:
1758:
1755:
1753:
1750:
1749:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1725:
1723:
1720:
1718:
1715:
1713:
1710:
1709:
1705:
1697:
1694:
1693:
1688:
1683:
1680:Compounds of
1675:
1670:
1668:
1663:
1661:
1656:
1655:
1652:
1646:
1643:
1641:
1638:
1637:
1633:
1623:
1620:
1614:
1609:
1605:
1601:
1600:
1595:
1593:
1592:Pisum sativum
1584:
1581:
1576:
1572:
1567:
1562:
1558:
1554:
1550:
1546:
1542:
1535:
1532:
1527:
1521:
1517:
1510:
1507:
1504:
1500:
1496:
1490:
1487:
1482:
1478:
1473:
1468:
1464:
1460:
1456:
1452:
1448:
1441:
1439:
1435:
1423:
1417:
1413:
1408:
1407:
1398:
1395:
1390:
1386:
1382:
1378:
1377:
1369:
1366:
1361:
1357:
1353:
1349:
1342:
1339:
1334:
1332:9780385671606
1328:
1324:
1317:
1314:
1310:
1306:
1301:
1298:
1293:
1289:
1285:
1281:
1278:(10): 1–423.
1277:
1273:
1266:
1263:
1258:
1254:
1250:
1246:
1242:
1238:
1234:
1230:
1223:
1220:
1215:
1211:
1207:
1203:
1202:
1194:
1191:
1186:
1182:
1178:
1174:
1173:
1165:
1162:
1157:
1151:
1143:
1139:
1135:
1131:
1127:
1123:
1116:
1114:
1110:
1105:
1099:
1095:
1091:
1087:
1086:
1077:
1075:
1073:
1069:
1062:
1058:
1055:
1054:
1050:
1048:
1046:
1042:
1038:
1034:
1030:
1026:
1022:
1016:
1014:
1010:
1006:
1002:
998:
994:
990:
986:
978:
976:
974:
970:
966:
959:
953:
946:
942:
938:
934:
930:
926:
922:
919:
915:
908:
904:
900:
896:
892:
888:
884:
880:
877:
873:
869:
865:
864:
863:
861:
857:
853:
847:
839:
837:
835:
827:
823:
819:
818:chlorosilanes
795:
794:
793:
787:
785:
783:
779:
775:
771:
767:
763:
759:
755:
747:
745:
743:
739:
731:
726:
703:4 NaPb + 4 CH
701:
699:
696:
692:
688:
684:
679:
677:
673:
669:
665:
664:electrophilic
661:
657:
652:
650:
646:
642:
638:
634:
630:
629:pseudohalides
626:
622:
618:
614:
610:
606:
602:
598:
594:
590:
586:
582:
577:
570:
565:
561:
560:
559:
558:can be used:
557:
541:
527:
516:
515:
514:
508:
492:
484:
476:
474:
472:
468:
467:Lucas reagent
440:
432:
411:
392:
377:
369:
361:
348:
347:
346:
344:
340:
339:zinc chloride
332:
294:
293:
292:
290:
266:
265:
264:
262:
258:
254:
246:
244:
241:
239:
235:
230:
228:
224:
220:
216:
210:From chlorine
209:
204:
202:
200:
196:
192:
187:
185:
184:chloromethane
181:
177:
173:
169:
165:
161:
157:
153:
149:
145:
141:
133:
131:
129:
128:leaving group
125:
120:
117:
113:
106:
104:
102:
98:
94:
90:
85:
83:
78:
74:
70:
66:
62:
58:
54:
50:
41:
37:
36:
32:
25:
20:
2348:Bond unknown
1781:
1622:
1603:
1597:
1591:
1583:
1551:(2): 320–3.
1548:
1544:
1534:
1515:
1509:
1494:
1489:
1454:
1450:
1425:. Retrieved
1405:
1397:
1380:
1374:
1368:
1351:
1347:
1341:
1322:
1316:
1300:
1275:
1271:
1265:
1232:
1228:
1222:
1205:
1199:
1193:
1176:
1170:
1164:
1150:cite journal
1125:
1122:J. Nat. Prod
1121:
1083:
1017:
982:
963:
916:site in the
852:insecticides
849:
815:
791:
782:dry cleaning
751:
735:
727:Applications
680:
668:nucleophilic
653:
578:
574:
553:
546:→ RCl + POCl
480:
464:
336:
286:
257:chloroethane
250:
242:
231:
213:
188:
137:
121:
112:Chlorination
110:
86:
73:chloroalkane
72:
56:
52:
48:
47:
1457:: 255–262.
1041:lamotrigine
975:concerns.
945:hydrophobic
941:hydrophilic
641:thiocyanate
532:→ 3 RCl + H
528:3 ROH + PCl
465:Called the
205:Preparation
191:epibatidine
164:fatty acids
152:amino acids
1348:BioScience
1103:3527306730
1063:References
1045:isoflurane
1037:sertraline
1033:loratadine
1029:vancomycin
960:Insulators
903:endosulfan
895:heptachlor
860:alicyclics
844:See also:
840:Pesticides
778:degreasing
758:chloroform
711:Cl → Pb(CH
609:thioethers
593:aryloxides
521:→ RCl + SO
517:ROH + SOCl
303:+ 2 HCl +
275:+ HCl → CH
263:with HCl:
229:catalyst.
227:Lewis acid
176:chloroform
156:flavonoids
142:including
101:chloroform
40:chloroform
2329:to carbon
1025:sucralose
899:chlordane
822:silicones
774:non-polar
656:magnesium
589:alkoxides
571:Reactions
542:ROH + PCl
412:−
382:Δ
362:−
195:analgesic
144:alkaloids
2364:Category
1575:16663416
1257:22662801
1142:19245259
1051:See also
1009:Lewisite
979:Toxicity
887:dieldrin
854:are the
748:Solvents
658:to give
631:such as
378:→
261:ethylene
160:steroids
148:terpenes
69:chlorine
67:atom of
2147:
1566:1066676
1481:2176589
1472:1567810
1427:11 July
1292:8795309
1237:Bibcode
925:dicofol
812:+ x HCl
744:(PVC).
649:alkynes
645:alkenes
637:cyanide
623:in the
599:in the
308:⁄
215:Alkanes
168:Dioxins
77:alkanes
75:class (
2319:Legend
1682:carbon
1573:
1563:
1522:
1479:
1469:
1418:
1414:–237.
1329:
1290:
1255:
1140:
1100:
1007:, and
935:, and
933:kepone
891:endrin
883:aldrin
832:) and
828:(CHClF
800:+ x Cl
691:sodium
676:sodium
639:, and
621:iodide
617:amines
613:amines
605:thiols
597:ethers
505:) and
427:halide
424:
317:→ ClCH
178:, and
162:, and
71:. The
929:mirex
698:alloy
633:azide
607:give
595:give
585:water
550:+ HCl
525:+ HCl
489:) or
485:(SOCl
421:alkyl
325:Cl +
116:water
55:, or
1571:PMID
1520:ISBN
1477:PMID
1429:2018
1416:ISBN
1327:ISBN
1288:PMID
1253:PMID
1156:link
1138:PMID
1098:ISBN
995:and
911:GABA
901:and
820:and
804:→ CH
780:and
768:and
695:lead
509:(PCl
493:(PCl
389:ZnCl
271:C=CH
232:The
219:aryl
217:and
99:and
82:TCDD
2293:CEs
2288:CCf
2283:CBk
2278:CCm
2273:CAm
2268:CPu
2263:CNp
2253:CPa
2248:CTh
2227:CYb
2222:CTm
2217:CEr
2212:CHo
2207:CDy
2202:CTb
2197:CGd
2192:CEu
2187:CSm
2182:CPm
2177:CNd
2172:CPr
2167:CCe
2162:CLa
2142:Og
2139:Ts
2136:Lv
2133:Mc
2130:Fl
2127:Nh
2124:Cn
2121:Rg
2118:Ds
2115:Mt
2112:Hs
2109:Bh
2105:CSg
2101:Db
2098:Rf
2082:CRa
2078:Fr
2073:Rn
2069:CAt
2064:CPo
2059:CBi
2054:CPb
2049:CTl
2044:CHg
2039:CAu
2034:CPt
2029:CIr
2024:COs
2019:CRe
2009:CTa
2004:CHf
1999:CLu
1987:CBa
1982:CCs
1975:CXe
1965:CTe
1960:CSb
1955:CSn
1950:CIn
1945:CCd
1940:CAg
1935:CPd
1930:CRh
1925:CRu
1920:CTc
1915:CMo
1910:CNb
1905:CZr
1893:CSr
1888:CRb
1881:CKr
1876:CBr
1871:CSe
1866:CAs
1861:CGe
1856:CGa
1851:CZn
1846:CCu
1841:CNi
1836:CCo
1831:CFe
1826:CMn
1821:CCr
1811:CTi
1806:CSc
1799:CCa
1787:CAr
1782:CCl
1767:CSi
1762:CAl
1757:CMg
1752:CNa
1746:Ne
1717:CBe
1712:CLi
1706:He
1608:doi
1561:PMC
1553:doi
1499:doi
1467:PMC
1459:doi
1412:235
1385:doi
1356:doi
1280:doi
1245:doi
1210:doi
1181:doi
1130:doi
1090:doi
997:DDD
993:DDE
989:DDT
943:or
856:DDT
806:4−x
647:or
591:or
583:or
513:):
373:HCl
299:=CH
287:In
2366::
2308:No
2303:Md
2298:Fm
2258:CU
2243:Ac
2094:Lr
2014:CW
1970:CI
1900:CY
1816:CV
1794:CK
1777:CS
1772:CP
1742:CF
1737:CO
1732:CN
1727:CC
1722:CB
1696:CH
1604:46
1602:.
1596:.
1569:.
1559:.
1549:74
1547:.
1543:.
1475:.
1465:.
1455:87
1453:.
1449:.
1437:^
1381:22
1379:.
1352:45
1350:.
1307:,
1286:.
1276:68
1274:.
1251:.
1243:.
1233:28
1231:.
1206:25
1204:.
1177:28
1175:.
1152:}}
1148:{{
1136:.
1126:72
1124:.
1112:^
1096:.
1071:^
1047:.
1003:,
931:,
927:,
897:,
893:,
889:,
885:,
808:Cl
796:CH
764:,
760:,
756:,
715:CH
707:CH
700::
678:.
651:.
635:,
536:PO
501:Cl
416:Cl
366:OH
345::
321:CH
295:CH
283:Cl
279:CH
174:,
166:.
158:,
154:,
150:,
146:,
95:,
91:,
59:,
42:.
1673:e
1666:t
1659:v
1616:.
1610::
1594:"
1577:.
1555::
1528:.
1501::
1483:.
1461::
1431:.
1391:.
1387::
1362:.
1358::
1335:.
1294:.
1282::
1259:.
1247::
1239::
1216:.
1212::
1187:.
1183::
1158:)
1144:.
1132::
1106:.
1092::
913:A
830:2
810:x
802:2
798:4
721:4
719:)
717:2
713:3
709:2
705:3
693:–
548:3
544:5
538:3
534:3
530:3
523:2
519:2
511:3
503:2
499:2
495:5
487:2
449:O
441:2
437:H
433:+
408:R
393:2
370:+
358:R
333:.
331:O
329:2
327:H
323:2
319:2
315:2
313:O
310:2
306:1
301:2
297:2
281:2
277:3
273:2
269:2
267:H
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