1028:
31:
1544:
1210:
Nature produces massive amounts of chloromethane and bromomethane. Most concern focuses on anthropogenic sources, which are potential toxins, even carcinogens. Similarly, great interest has been shown in remediation of man made halocarbons such as those produced on large scale, such as dry cleaning
132:
was produced in the 15th century. The systematic synthesis of such compounds developed in the 19th century in step with the development of organic chemistry and the understanding of the structure of alkanes. Methods were developed for the selective formation of C-halogen bonds. Especially versatile
238:
Haloalkanes generally resemble the parent alkanes in being colorless, relatively odorless, and hydrophobic. The melting and boiling points of chloro-, bromo-, and iodoalkanes are higher than the analogous alkanes, scaling with the atomic weight and number of halides. This effect is due to the
1411:
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).
867:); the halogen is replaced by the respective group. This is of great synthetic utility: chloroalkanes are often inexpensively available. For example, after undergoing substitution reactions, cyanoalkanes may be hydrolyzed to carboxylic acids, or reduced to primary amines using
422:. In this reaction a hydrogen atom is removed from the alkane, then replaced by a halogen atom by reaction with a diatomic halogen molecule. Free radical halogenation typically produces a mixture of compounds mono- or multihalogenated at various positions.
1211:
fluids. Volatile halocarbons degrade photochemically because the carbon-halogen bond can be labile. Some microorganisms dehalogenate halocarbons. While this behavior is intriguing, the rates of remediation are generally very slow.
318:
than the corresponding alkanes because of their increased polarity. Haloalkanes containing halogens other than fluorine are more reactive than the parent alkanes—it is this reactivity that is the basis of most controversies. Many are
141:
to alkyl halides. These methods are so reliable and so easily implemented that haloalkanes became cheaply available for use in industrial chemistry because the halide could be further replaced by other functional groups.
121:, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see
323:, with primary haloalkanes and those containing heavier halogens being the most active (fluoroalkanes do not act as alkylating agents under normal conditions). The ozone-depleting abilities of the CFCs arises from the
745:. Upon heating this solution with copper(I) chloride, the diazonium group is replaced by -Cl. This is a comparatively easy method to make aryl halides as the gaseous product can be separated easily from aryl halide.
279:) is a liquid. Many fluoroalkanes, however, go against this trend and have lower melting and boiling points than their nonfluorinated analogues due to the decreased polarizability of fluorine. For example,
183:). In secondary (2°) haloalkanes, the carbon that carries the halogen atom has two C–C bonds. In tertiary (3°) haloalkanes, the carbon that carries the halogen atom has three C–C bonds.
153:
From the structural perspective, haloalkanes can be classified according to the connectivity of the carbon atom to which the halogen is attached. In primary (1°) haloalkanes, the
462:
states that under normal conditions, hydrogen is attached to the unsaturated carbon with the most hydrogen substituents. The rule is violated when neighboring functional groups
821:
being a common source of this ion). This OH is a nucleophile with a clearly negative charge, as it has excess electrons it donates them to the carbon, which results in a
1414:
1342:
125:. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen (F, Cl, Br, I).
458:) to form a mono-haloalkane. The double bond of the alkene is replaced by two new bonds, one with the halogen and one with the hydrogen atom of the hydrohalic acid.
218:
compounds, respectively. Compounds containing more than one kind of halogen are also possible. Several classes of widely used haloalkanes are classified in this way
1496:
Weber, Lutz W. D.; Boll, Meinrad; Stampfl, Andreas (2003). "Hepatotoxicity and
Mechanism of Action of Haloalkanes: Carbon Tetrachloride as a Toxicological Model".
186:
Haloalkanes can also be classified according to the type of halogen on group 17 responding to a specific halogenoalkane. Haloalkanes containing carbon bonded to
1050:
An estimated one fifth of pharmaceuticals contain fluorine, including several of the top drugs. Most of these compounds are alkyl fluorides. Examples include
1576:
2495:
404:
Haloalkanes can be produced from virtually all organic precursors. From the perspective of industry, the most important ones are alkanes and alkenes.
2500:
314:
As they contain fewer C–H bonds, haloalkanes are less flammable than alkanes, and some are used in fire extinguishers. Haloalkanes are better
1263:
1287:
Gribble, Gordon (2023). Kinghorn, A. Douglas; Falk, Heinz; Gibbons, Simon; Asakawa, Yoshinori; Liu, Ji-Kai; Dirsch, Verena M. Cham (eds.).
1359:
1223:, haloalkanes are potential carcinogens. The more reactive members of this large class of compounds generally pose greater risk, e.g.
485:. Alkynes react similarly, forming the tetrahalo compounds. This is sometimes known as "decolorizing" the halogen, since the reagent X
388:. However, many of these compounds have already an established trivial name, which is endorsed by the IUPAC nomenclature, for example
1296:
1569:
396:). But nowadays, IUPAC nomenclature is used. To reduce confusion this article follows the systematic naming scheme throughout.
1431:
1375:
37:(a haloalkane) is a colorless liquid that boils well below room temperature (as seen here) and can be extracted from common
2528:
2399:
531:
In the laboratory, more active deoxygenating and halogenating agents combine with base to effect the conversion. In the "
1130:
are useful solvents. Several million tons of chlorinated methanes are produced annually. Chloromethane is a precursor to
2538:
1972:
1562:
876:
868:
482:
419:
413:
2009:
667:
556:
508:. However, some exceptions are known: ionic liquids suppress the formation or promote the cleavage of ethers,
230:(HFCs). These abbreviations are particularly common in discussions of the environmental impact of haloalkanes.
223:
203:
109:
is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the
2482:
1016:
244:
1548:
2382:
996:
796:
572:
324:
211:
69:, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as
2533:
2489:
2377:
1139:
1040:
960:
O and NaBr. Thus, haloalkanes can be converted to alkenes. Similarly, dihaloalkanes can be converted to
892:
792:
679:
592:
471:
215:
1154:
Large scale applications of alkyl bromides exploit their toxicity, which also limits their usefulness.
459:
1398:
Ann M. Thayer "Fabulous
Fluorine" Chemical and Engineering News, June 5, 2006, Volume 84, pp. 15-24.
987:
Haloalkanes undergo free-radical reactions with elemental magnesium to give alkyl-magnesium compound:
813:
breaks a bond, is a good example of the nucleophilic nature of haloalkanes. The polar bond attracts a
2523:
2458:
1903:
1224:
1201:
became known, their use was increasingly restricted, and they have now largely been replaced by HFCs.
1194:
872:
841:
829:
resulting in a halide ion, X. As can be seen, the OH is now attached to the alkyl group, creating an
699:
636:
532:
385:
361:
339:
are produced annually by natural sources. The oceans are estimated to release 1 to 2 million tons of
240:
999:. Both Grignard reagents and organolithium compounds behave as the R synthon. Alkali metals such as
683:
93:. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious
1764:
1182:
1083:
933:
927:
830:
826:
777:
497:
219:
138:
1035:
Chlorinated or fluorinated alkenes undergo polymerization. Important halogenated polymers include
1521:
1036:
1012:
738:
727:
671:
659:
651:
357:
296:
264:
227:
98:
2448:
2418:
2176:
1798:
1513:
1478:
1427:
1355:
1292:
1269:
1259:
1171:
888:
884:
765:
714:
Many chloro and bromoalkanes are formed naturally. The principal pathways involve the enzymes
525:
513:
509:
443:
431:
134:
74:
34:
2153:
1647:
1585:
1505:
1468:
1460:
1419:
1347:
1322:
1251:
1220:
988:
936:
reactions, the halogen and an adjacent proton are removed from halocarbons, thus forming an
915:
880:
810:
749:
715:
588:
536:
466:
the multiple bond, or in certain additions of hydrogen bromide (addition in the presence of
451:
320:
248:
2372:
2131:
2126:
2109:
2092:
1893:
1642:
1314:
1198:
1127:
1119:
773:
769:
719:
695:
501:
393:
102:
70:
30:
1399:
1027:
17:
2443:
2438:
2314:
2309:
2304:
2097:
2064:
1848:
1830:
1820:
1291:. Progress in the Chemistry of Organic Natural Products. Switzerland: Springer Nature.
1155:
1123:
1087:
1051:
1008:
742:
703:
655:
643:
463:
207:
157:
that carries the halogen atom is only attached to one other alkyl group. An example is
114:
106:
90:
1473:
1448:
2517:
2463:
2411:
2342:
2228:
2218:
2213:
2203:
2198:
2148:
2143:
2059:
2054:
2044:
1898:
1853:
1815:
1803:
1774:
1652:
1167:
1067:
1055:
845:
521:
336:
118:
1449:"Bacterial dehalogenases: Biochemistry, genetics, and biotechnological applications"
2394:
2281:
2276:
2253:
2004:
1843:
1769:
1706:
1701:
1679:
1635:
1620:
1610:
1464:
1186:
1131:
647:
439:
340:
158:
129:
1525:
1423:
599:). The heavier halogens do not require preformed reagents: A catalytic amount of
2453:
2406:
2367:
2248:
2136:
2121:
2116:
2104:
1669:
1664:
1630:
1625:
1615:
1593:
1190:
1099:
1075:
1011:, giving symmetrical alkanes. Haloalkanes, especially iodoalkanes, also undergo
941:
860:
781:
761:
675:
373:
122:
110:
78:
27:
Group of chemical compounds derived from alkanes containing one or more halogens
2353:
2233:
2188:
2084:
2049:
2039:
1979:
1915:
1838:
1786:
1115:
1103:
1095:
1071:
1063:
1059:
903:
806:
628:
517:
389:
82:
66:
38:
1351:
1273:
145:
While many haloalkanes are human-produced, substantial amounts are biogenic.
2329:
2243:
2208:
2193:
2181:
2024:
1999:
1808:
1158:
is also an effective fumigant, but its production and use are controversial.
1091:
814:
467:
94:
1517:
247:
to dipole-dipole interaction because of the increased polarizability. Thus
1543:
1482:
1255:
1245:
914:-substituted amines, and thioethers respectively. They are substituted by
795:
involve the replacement of the halogen with another molecule—thus leaving
2337:
2291:
2258:
1954:
1860:
1734:
1689:
1674:
1312:
Gordon W. Gribble (1998). "Naturally
Occurring Organohalogen Compounds".
1135:
896:
849:
822:
748:
When an iodide is to be made, copper chloride is not needed. Addition of
663:
552:
381:
191:
187:
2299:
2223:
2074:
2069:
2034:
2019:
2014:
1984:
1967:
1791:
1718:
1684:
1004:
992:
976:
972:
949:
945:
856:
834:
800:
377:
369:
315:
280:
195:
86:
62:
1509:
1326:
113:, but fluorinated volatile haloalkanes in theory may have activity as
2387:
2319:
2163:
1872:
1865:
1759:
1740:
1729:
1713:
1659:
1079:
1000:
961:
953:
937:
632:
435:
365:
199:
154:
58:
1554:
768:
molecules: the carbon to which the halogen is attached is slightly
2268:
2238:
2171:
2029:
1994:
1989:
1962:
1910:
1877:
1781:
1605:
1026:
907:
864:
840:
Chloro- and bromoalkanes are readily substituted by iodide in the
799:, as well as the halogenated product. Haloalkanes behave as the R
734:
505:
29:
611:
may be used for the transformation using phosphorus and bromine;
587:) function similarly, and alcohols convert to bromoalkanes under
1696:
1376:"Haloalkanes & Chloroform: Class 12 Organic Chemistry Notes"
968:
1558:
967:
In related reactions, 1,2-dibromocompounds are debrominated by
512:
converts tertiary alcohols to choloroalkanes, and primary and
489:
is colored and the product is usually colorless and odorless.
481:) to form haloalkanes with two neighboring halogen atoms in a
844:. The iodoalkanes produced easily undergo further reaction.
1380:
NEB Notes: SEE, Class 11, Class 12 Notes
Exercise Questions
1114:
Some low molecular weight chlorinated hydrocarbons such as
682:; the coproducts are triphenylphosphine oxide and a
1166:
No large scale applications are known for alkyl iodides.
918:
to give magnesium salts and an extended alkyl compound.
500:
can be converted to haloalkanes. Direct reaction with a
65:
substituents. They are a subset of the general class of
133:
methods included the addition of halogens to alkenes,
1400:
http://pubs.acs.org/cen/coverstory/84/8423cover1.html
948:, the hydroxide ion HO abstracts a hydrogen atom. A
879:. Amines may also be prepared from alkyl halides in
2431:
2351:
2328:
2290:
2267:
2162:
2083:
1953:
1930:
1886:
1829:
1752:
1727:
1592:
780:(electrophilic) carbon which, inevitably, attracts
627:. Iodoalkanes may similarly be prepared using red
555:converts less reactive alcohols to chlorides. Both
1197:. Starting in the 1980s, as their contribution to
871:. Azoalkanes may be reduced to primary amines by
833:. (Hydrolysis of bromoethane, for example, yields
694:Two methods for the synthesis of haloalkanes from
855:Haloalkanes react with ionic nucleophiles (e.g.
504:rarely gives a pure product, instead generating
295:) has a melting point of −182.5 °C whereas
891:, by undergoing nucleophilic substitution with
837:). Reactions with ammonia give primary amines.
356:The formal naming of haloalkanes should follow
1415:Ullmann's Encyclopedia of Industrial Chemistry
1343:Ullmann's Encyclopedia of Industrial Chemistry
1193:due to their relatively low toxicity and high
975:dihalides can react with strong bases to give
41:canisters by simply inverting them during use.
1570:
1250:. Saul Patai. London: John Wiley & Sons.
752:with gentle shaking produces the haloalkane.
8:
825:bond between the two. Thus C–X is broken by
1289:Naturally Occurring Organohalogen Compounds
1007:are able to cause haloalkanes to couple in
474:) which occur by a free-radical mechanism.
392:(trichloromethane) and methylene chloride (
128:Haloalkanes have been known for centuries.
1950:
1749:
1577:
1563:
1555:
1472:
311:) has a melting point of −183.6 °C.
1247:The chemistry of the carbon-halogen bond
1236:
906:alcohols, amines, and thiols to obtain
902:In the presence of a base, haloalkanes
803:, and readily react with nucleophiles.
516:convert similarly in the presence of a
438:reacts with a dry hydrogen halide (HX)
899:respectively, followed by hydrolysis.
658:, the reagent is tetrahalomethane and
7:
1346:. Weinheim: Wiley-VCH. p. 557.
1086:, including the commercial products
477:Alkenes also react with halogens (X
1170:is a popular methylating agent in
137:of alkenes, and the conversion of
25:
1447:Fetzner, S.; Lingens, F. (1994).
760:Haloalkanes are reactive towards
524:. The latter is exploited in the
335:An estimated 4,100,000,000 kg of
1542:
1185:were used almost universally as
952:ion is then lost, resulting in
944:and sodium hydroxide (NaOH) in
418:Alkanes react with halogens by
1498:Critical Reviews in Toxicology
1465:10.1128/mmbr.58.4.641-685.1994
991:. Haloalkanes also react with
772:where the halogen is slightly
1:
1424:10.1002/14356007.a06_233.pub2
360:, which put the halogen as a
97:and toxins. For example, the
1412:"Chlorinated Hydrocarbons".
1206:Environmental considerations
678:, triphenylphosphine, and a
364:to the alkane. For example,
101:have been shown to lead to
2555:
925:
411:
239:increased strength of the
2472:
1244:Patai, Saul, ed. (1973).
1146:) is used to make teflon.
971:dust to give alkenes and
877:lithium aluminium hydride
869:lithium aluminium hydride
483:halogen addition reaction
420:free radical halogenation
414:Free radical halogenation
1352:10.1002/14356007.l14_l01
1017:organometallic compounds
668:triphenylphosphine oxide
557:phosphorus pentachloride
426:From alkenes and alkynes
224:hydrochlorofluorocarbons
18:Halogenated hydrocarbons
2483:chemical classification
1453:Microbiological Reviews
1418:. Weinheim: Wiley-VCH.
1078:. Fluorine-substituted
997:organolithium compounds
674:, the reagents are any
61:containing one or more
1032:
809:, a reaction in which
797:saturated hydrocarbons
793:Substitution reactions
741:ions in a solution of
725:
662:; the co-products are
573:phosphorus trichloride
42:
2490:chemical nomenclature
1256:10.1002/9780470771280
1140:Chlorodifluoromethane
1041:polytetrafluoroethene
1030:
940:. For example, with
893:potassium phthalimide
776:. This results in an
690:From carboxylic acids
593:phosphorus tribromide
472:Wohl-Ziegler reaction
263:) is a solid whereas
241:intermolecular forces
33:
2529:Halogenated solvents
1551:at Wikimedia Commons
1225:carbon tetrachloride
1195:heat of vaporization
1084:volatile anesthetics
873:Staudinger reduction
842:Finkelstein reaction
700:Hunsdiecker reaction
637:phosphorus triiodide
533:Darzens halogenation
1946:not C, H or O)
1183:Chlorofluorocarbons
1179:Chlorofluorocarbons
1043:(PTFE, or teflon).
934:dehydrohalogenation
928:Dehydrohalogenation
827:heterolytic fission
520:activator, such as
220:chlorofluorocarbons
99:chlorofluorocarbons
75:fire extinguishants
2388:Hypervalent iodine
1037:polyvinyl chloride
1033:
1015:reactions to give
1013:oxidative addition
778:electron deficient
728:Sandmeyer's Method
680:diazodicarboxylate
672:Mitsunobu reaction
660:triphenylphosphine
652:triphenylphosphine
514:secondary alcohols
460:Markovnikov's rule
386:tetrachloromethane
358:IUPAC nomenclature
331:Natural occurrence
327:of the C–Cl bond.
297:tetrafluoromethane
265:tetrachloromethane
228:hydrofluorocarbons
43:
2539:Functional groups
2511:
2510:
2449:Sulfenyl chloride
2427:
2426:
1926:
1925:
1745:(only C, H and O)
1586:Functional groups
1547:Media related to
1510:10.1080/713611034
1340:"Ionic liquids".
1327:10.1021/ar9701777
1265:978-0-470-77128-0
1221:alkylating agents
1172:organic synthesis
889:Delepine reaction
885:Gabriel synthesis
733:Primary aromatic
510:hydrochloric acid
444:hydrogen chloride
432:hydrohalogenation
321:alkylating agents
245:London dispersion
135:hydrohalogenation
35:Tetrafluoroethane
16:(Redirected from
2546:
2478:
2383:Trifluoromethoxy
1951:
1947:
1750:
1746:
1599:
1579:
1572:
1565:
1556:
1546:
1530:
1529:
1493:
1487:
1486:
1476:
1444:
1438:
1437:
1408:
1402:
1396:
1390:
1389:
1387:
1386:
1372:
1366:
1365:
1337:
1331:
1330:
1309:
1303:
1302:
1284:
1278:
1277:
1241:
1031:Teflon structure
989:Grignard reagent
916:Grignard reagent
881:amine alkylation
750:potassium iodide
716:chloroperoxidase
696:carboxylic acids
622:
621:
620:
610:
609:
608:
589:hydrobromic acid
586:
585:
584:
570:
569:
568:
550:
549:
548:
537:thionyl chloride
457:
452:hydrogen bromide
449:
310:
309:
308:
294:
293:
292:
278:
277:
276:
262:
261:
260:
249:tetraiodomethane
182:
180:
179:
171:
170:
115:greenhouse gases
71:flame retardants
21:
2554:
2553:
2549:
2548:
2547:
2545:
2544:
2543:
2514:
2513:
2512:
2507:
2476:
2468:
2423:
2378:Trichloromethyl
2373:Trifluoromethyl
2347:
2324:
2286:
2263:
2158:
2127:Phosphine oxide
2079:
1945:
1943:
1942:
1940:
1938:
1936:
1934:
1932:
1922:
1882:
1825:
1744:
1743:
1738:
1733:
1723:
1597:
1596:
1588:
1583:
1539:
1534:
1533:
1495:
1494:
1490:
1446:
1445:
1441:
1434:
1410:
1409:
1405:
1397:
1393:
1384:
1382:
1374:
1373:
1369:
1362:
1339:
1338:
1334:
1315:Acc. Chem. Res.
1311:
1310:
1306:
1299:
1286:
1285:
1281:
1266:
1243:
1242:
1238:
1233:
1217:
1208:
1199:ozone depletion
1145:
1128:trichloroethane
1120:dichloromethane
1111:Alkyl chlorides
1047:Alkyl fluorides
1025:
985:
959:
930:
924:
820:
790:
774:electronegative
770:electropositive
758:
731:
726:From amines by
720:bromoperoxidase
712:
692:
644:named reactions
635:(equivalent to
619:
616:
615:
614:
612:
607:
604:
603:
602:
600:
598:
583:
580:
579:
578:
576:
567:
564:
563:
562:
560:
547:
544:
543:
542:
540:
502:hydrohalic acid
495:
488:
480:
455:
447:
428:
416:
410:
402:
394:dichloromethane
384:groups becomes
354:
349:
333:
307:
304:
303:
302:
300:
291:
288:
287:
286:
284:
275:
272:
271:
270:
268:
259:
256:
255:
254:
252:
236:
178:
175:
174:
173:
169:
166:
165:
164:
162:
151:
103:ozone depletion
91:pharmaceuticals
51:halogenoalkanes
49:(also known as
28:
23:
22:
15:
12:
11:
5:
2552:
2550:
2542:
2541:
2536:
2531:
2526:
2516:
2515:
2509:
2508:
2506:
2505:
2504:
2503:
2498:
2486:
2479:
2473:
2470:
2469:
2467:
2466:
2464:Sulfinylamines
2461:
2456:
2451:
2446:
2444:Phosphoramides
2441:
2439:Isothiocyanate
2435:
2433:
2429:
2428:
2425:
2424:
2422:
2421:
2416:
2415:
2414:
2404:
2403:
2402:
2392:
2391:
2390:
2385:
2380:
2375:
2370:
2359:
2357:
2349:
2348:
2346:
2345:
2340:
2334:
2332:
2326:
2325:
2323:
2322:
2317:
2315:Selenenic acid
2312:
2310:Seleninic acid
2307:
2305:Selenonic acid
2302:
2296:
2294:
2288:
2287:
2285:
2284:
2279:
2273:
2271:
2265:
2264:
2262:
2261:
2256:
2251:
2246:
2241:
2236:
2231:
2226:
2221:
2216:
2211:
2206:
2201:
2196:
2191:
2186:
2185:
2184:
2174:
2168:
2166:
2160:
2159:
2157:
2156:
2151:
2146:
2141:
2140:
2139:
2129:
2124:
2119:
2114:
2113:
2112:
2102:
2101:
2100:
2098:Phosphodiester
2089:
2087:
2081:
2080:
2078:
2077:
2072:
2067:
2062:
2057:
2052:
2047:
2042:
2037:
2032:
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1976:
1975:
1970:
1959:
1957:
1948:
1944:(one element,
1928:
1927:
1924:
1923:
1921:
1920:
1919:
1918:
1908:
1907:
1906:
1901:
1890:
1888:
1884:
1883:
1881:
1880:
1875:
1870:
1869:
1868:
1858:
1857:
1856:
1851:
1846:
1835:
1833:
1827:
1826:
1824:
1823:
1821:Methylenedioxy
1818:
1813:
1812:
1811:
1806:
1796:
1795:
1794:
1789:
1779:
1778:
1777:
1767:
1762:
1756:
1754:
1747:
1725:
1724:
1722:
1721:
1716:
1711:
1710:
1709:
1704:
1694:
1693:
1692:
1687:
1682:
1677:
1672:
1667:
1657:
1656:
1655:
1650:
1640:
1639:
1638:
1633:
1628:
1623:
1618:
1613:
1602:
1600:
1598:(only C and H)
1590:
1589:
1584:
1582:
1581:
1574:
1567:
1559:
1553:
1552:
1538:
1537:External links
1535:
1532:
1531:
1504:(2): 105–136.
1488:
1459:(4): 641–685.
1439:
1432:
1403:
1391:
1367:
1361:978-3527306732
1360:
1332:
1321:(3): 141–152.
1304:
1297:
1279:
1264:
1235:
1234:
1232:
1229:
1216:
1213:
1207:
1204:
1203:
1202:
1180:
1176:
1175:
1164:
1160:
1159:
1156:Methyl bromide
1152:
1151:Alkyl bromides
1148:
1147:
1143:
1124:dichloroethene
1112:
1108:
1107:
1088:methoxyflurane
1052:5-fluorouracil
1048:
1024:
1021:
1009:Wurtz reaction
995:metal to give
984:
981:
957:
926:Main article:
923:
920:
848:is used as a
818:
789:
786:
757:
754:
743:sodium nitrite
730:
724:
711:
708:
704:Kochi reaction
691:
688:
684:hydrazodiamide
656:Appel reaction
646:relies on the
642:One family of
617:
605:
596:
581:
565:
545:
494:
491:
486:
478:
427:
424:
412:Main article:
409:
406:
401:
398:
353:
350:
348:
345:
332:
329:
305:
289:
273:
257:
235:
232:
208:organochlorine
204:organofluorine
176:
167:
150:
147:
107:Methyl bromide
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2551:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2521:
2519:
2502:
2499:
2497:
2494:
2493:
2492:
2491:
2487:
2485:
2484:
2480:
2475:
2474:
2471:
2465:
2462:
2460:
2457:
2455:
2452:
2450:
2447:
2445:
2442:
2440:
2437:
2436:
2434:
2430:
2420:
2417:
2413:
2410:
2409:
2408:
2405:
2401:
2398:
2397:
2396:
2393:
2389:
2386:
2384:
2381:
2379:
2376:
2374:
2371:
2369:
2366:
2365:
2364:
2361:
2360:
2358:
2356:
2355:
2350:
2344:
2343:Telluroketone
2341:
2339:
2336:
2335:
2333:
2331:
2327:
2321:
2318:
2316:
2313:
2311:
2308:
2306:
2303:
2301:
2298:
2297:
2295:
2293:
2289:
2283:
2280:
2278:
2275:
2274:
2272:
2270:
2266:
2260:
2257:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2235:
2232:
2230:
2229:Sulfonic acid
2227:
2225:
2222:
2220:
2219:Sulfinic acid
2217:
2215:
2214:Thiosulfonate
2212:
2210:
2207:
2205:
2204:Thiosulfinate
2202:
2200:
2199:Sulfenic acid
2197:
2195:
2192:
2190:
2187:
2183:
2180:
2179:
2178:
2175:
2173:
2170:
2169:
2167:
2165:
2161:
2155:
2154:Phosphaallene
2152:
2150:
2149:Phosphaalkyne
2147:
2145:
2144:Phosphaalkene
2142:
2138:
2135:
2134:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2111:
2108:
2107:
2106:
2103:
2099:
2096:
2095:
2094:
2091:
2090:
2088:
2086:
2082:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1974:
1971:
1969:
1966:
1965:
1964:
1961:
1960:
1958:
1956:
1952:
1949:
1929:
1917:
1914:
1913:
1912:
1909:
1905:
1902:
1900:
1897:
1896:
1895:
1892:
1891:
1889:
1885:
1879:
1876:
1874:
1871:
1867:
1864:
1863:
1862:
1859:
1855:
1852:
1850:
1847:
1845:
1842:
1841:
1840:
1837:
1836:
1834:
1832:
1828:
1822:
1819:
1817:
1816:Ethylenedioxy
1814:
1810:
1807:
1805:
1802:
1801:
1800:
1797:
1793:
1790:
1788:
1785:
1784:
1783:
1780:
1776:
1773:
1772:
1771:
1768:
1766:
1763:
1761:
1758:
1757:
1755:
1751:
1748:
1742:
1736:
1731:
1726:
1720:
1717:
1715:
1712:
1708:
1705:
1703:
1700:
1699:
1698:
1695:
1691:
1688:
1686:
1683:
1681:
1678:
1676:
1673:
1671:
1668:
1666:
1663:
1662:
1661:
1658:
1654:
1651:
1649:
1646:
1645:
1644:
1641:
1637:
1634:
1632:
1629:
1627:
1624:
1622:
1619:
1617:
1614:
1612:
1609:
1608:
1607:
1604:
1603:
1601:
1595:
1591:
1587:
1580:
1575:
1573:
1568:
1566:
1561:
1560:
1557:
1550:
1545:
1541:
1540:
1536:
1527:
1523:
1519:
1515:
1511:
1507:
1503:
1499:
1492:
1489:
1484:
1480:
1475:
1470:
1466:
1462:
1458:
1454:
1450:
1443:
1440:
1435:
1429:
1425:
1421:
1417:
1416:
1407:
1404:
1401:
1395:
1392:
1381:
1377:
1371:
1368:
1363:
1357:
1353:
1349:
1345:
1344:
1336:
1333:
1328:
1324:
1320:
1317:
1316:
1308:
1305:
1300:
1298:3-031-26629-3
1294:
1290:
1283:
1280:
1275:
1271:
1267:
1261:
1257:
1253:
1249:
1248:
1240:
1237:
1230:
1228:
1226:
1222:
1214:
1212:
1205:
1200:
1196:
1192:
1188:
1184:
1181:
1178:
1177:
1173:
1169:
1168:Methyl iodide
1165:
1163:Alkyl iodides
1162:
1161:
1157:
1153:
1150:
1149:
1141:
1137:
1133:
1132:chlorosilanes
1129:
1125:
1121:
1117:
1113:
1110:
1109:
1105:
1101:
1097:
1093:
1089:
1085:
1081:
1077:
1073:
1069:
1068:ciprofloxacin
1065:
1061:
1057:
1056:flunitrazepam
1053:
1049:
1046:
1045:
1044:
1042:
1038:
1029:
1022:
1020:
1018:
1014:
1010:
1006:
1002:
998:
994:
990:
982:
980:
978:
974:
970:
965:
963:
955:
951:
947:
943:
939:
935:
929:
921:
919:
917:
913:
909:
905:
900:
898:
894:
890:
886:
882:
878:
874:
870:
866:
862:
858:
853:
851:
847:
846:Sodium iodide
843:
838:
836:
832:
828:
824:
817:ion, OH (NaOH
816:
812:
808:
804:
802:
798:
794:
787:
785:
783:
779:
775:
771:
767:
763:
755:
753:
751:
746:
744:
740:
736:
729:
723:
721:
717:
709:
707:
705:
701:
697:
689:
687:
685:
681:
677:
673:
669:
665:
661:
657:
653:
649:
648:deoxygenating
645:
640:
638:
634:
630:
626:
594:
590:
574:
558:
554:
538:
534:
529:
527:
523:
522:zinc chloride
519:
515:
511:
507:
503:
499:
493:From alcohols
492:
490:
484:
475:
473:
469:
465:
461:
453:
445:
441:
437:
433:
425:
423:
421:
415:
407:
405:
399:
397:
395:
391:
387:
383:
379:
375:
371:
367:
363:
359:
351:
346:
344:
342:
338:
337:chloromethane
330:
328:
326:
325:photolability
322:
317:
312:
298:
282:
266:
250:
246:
242:
233:
231:
229:
225:
221:
217:
213:
212:organobromine
209:
205:
201:
197:
193:
189:
184:
160:
156:
148:
146:
143:
140:
136:
131:
126:
124:
120:
119:Methyl iodide
116:
112:
108:
104:
100:
96:
92:
88:
84:
80:
76:
72:
68:
64:
60:
56:
55:alkyl halides
52:
48:
40:
36:
32:
19:
2534:Refrigerants
2488:
2481:
2395:Vinyl halide
2362:
2352:
2282:Borinic acid
2277:Boronic acid
2254:Thioxanthate
1594:Hydrocarbons
1501:
1497:
1491:
1456:
1452:
1442:
1413:
1406:
1394:
1383:. Retrieved
1379:
1370:
1341:
1335:
1318:
1313:
1307:
1288:
1282:
1246:
1239:
1218:
1209:
1187:refrigerants
1058:(Rohypnol),
1034:
1023:Applications
986:
966:
931:
911:
901:
854:
839:
805:
791:
788:Substitution
782:nucleophiles
762:nucleophiles
759:
747:
732:
713:
710:Biosynthesis
693:
641:
624:
530:
496:
476:
440:electrophile
429:
417:
408:From alkanes
403:
355:
347:Nomenclature
341:bromomethane
334:
313:
237:
226:(HCFCs) and
216:organoiodine
185:
159:chloroethane
152:
144:
130:Chloroethane
127:
79:refrigerants
54:
50:
46:
44:
2524:Haloalkanes
2459:Thiocyanate
2454:Sulfonamide
2419:Perchlorate
2407:Acyl halide
2368:Fluoroethyl
2249:Thionoester
2137:Phosphonium
2122:Phosphinate
2117:Phosphonous
2105:Phosphonate
1804:Hydroperoxy
1626:Cyclopropyl
1549:Haloalkanes
1191:propellants
1100:sevoflurane
1076:fluconazole
1039:(PVC), and
942:bromoethane
922:Elimination
861:thiocyanate
764:. They are
676:nucleophile
374:bromoethane
202:results in
123:Halomethane
111:ozone layer
83:propellants
67:halocarbons
47:haloalkanes
2518:Categories
2363:Haloalkane
2234:Thioketone
2189:Persulfide
2085:Phosphorus
2050:Isocyanate
2040:Isonitrile
1941:or oxygen
1939:hydrogen,
1935:not being
1916:Orthoester
1809:Dioxiranes
1787:Enol ether
1675:1-Propenyl
1433:3527306730
1385:2023-01-07
1231:References
1116:chloroform
1104:desflurane
1096:isoflurane
1072:mefloquine
1064:paroxetine
1062:(Prozac),
1060:fluoxetine
807:Hydrolysis
670:. In the
654:. In the
650:effect of
629:phosphorus
623:is formed
526:Lucas test
518:Lewis acid
400:Production
390:chloroform
380:with four
343:annually.
234:Properties
95:pollutants
39:canned air
2496:inorganic
2330:Tellurium
2244:Thioester
2209:Sulfoxide
2194:Disulfide
2182:Sulfonium
2132:Phosphine
2110:Phosphite
2093:Phosphate
2025:Carbamate
2000:Hydrazone
1933:element,
1931:Only one
1904:Anhydride
1643:Methylene
1274:520990502
1136:silicones
1092:enflurane
1070:(Cipro),
1066:(Paxil),
815:hydroxide
756:Reactions
739:diazonium
468:peroxides
2477:See also
2412:Chloride
2338:Tellurol
2292:Selenium
2259:Xanthate
1973:Ammonium
1955:Nitrogen
1937:carbon,
1894:Carboxyl
1861:Aldehyde
1849:Acryloyl
1831:carbonyl
1735:hydrogen
1690:Cumulene
1518:12708612
977:carbenes
904:alkylate
897:hexamine
850:catalyst
823:covalent
664:haloform
553:pyridine
470:and the
464:polarize
382:chlorine
372:becomes
316:solvents
222:(CFCs),
192:chlorine
188:fluorine
139:alcohols
87:solvents
2501:organic
2300:Selenol
2224:Sulfone
2177:Sulfide
2075:NONOate
2070:Nitroso
2060:Nitrite
2055:Nitrate
2045:Cyanate
2035:Nitrile
2020:Amidine
2015:Imidate
1985:Nitrene
1980:Hydrazo
1968:Enamine
1899:Acetoxy
1887:carboxy
1854:Benzoyl
1792:Epoxide
1775:Methoxy
1765:Alcohol
1719:Carbene
1653:Methine
1483:7854251
1005:lithium
993:lithium
973:geminal
962:alkynes
950:Bromide
946:ethanol
857:cyanide
835:ethanol
831:alcohol
801:synthon
625:in situ
551:) with
498:Alcohol
378:methane
370:bromine
281:methane
196:bromine
149:Classes
63:halogen
59:alkanes
2400:Iodide
2320:Selone
2164:Sulfur
1873:Ketone
1866:Ketene
1844:Acetyl
1799:Peroxy
1770:Alkoxy
1760:Acetal
1741:oxygen
1730:carbon
1714:Alkyne
1707:Benzyl
1702:Phenyl
1685:Allene
1680:Crotyl
1660:Alkene
1648:Bridge
1636:Pentyl
1621:Propyl
1611:Methyl
1526:435416
1524:
1516:
1481:
1474:372986
1471:
1430:
1358:
1295:
1272:
1262:
1215:Safety
1142:(CHClF
1126:, and
1080:ethers
1001:sodium
954:ethene
938:alkene
908:ethers
737:yield
735:amines
633:iodine
571:) and
506:ethers
436:alkene
366:ethane
362:prefix
243:—from
200:iodine
198:, and
155:carbon
89:, and
57:) are
2432:Other
2269:Boron
2239:Thial
2172:Thiol
2065:Nitro
2030:Imide
2010:Amide
1995:Oxime
1990:Imine
1963:Amine
1911:Ester
1878:Ynone
1782:Ether
1753:R-O-R
1728:Only
1670:Allyl
1665:Vinyl
1631:Butyl
1616:Ethyl
1606:Alkyl
1522:S2CID
983:Other
865:azide
811:water
766:polar
702:and
698:are
450:) or
442:like
434:, an
368:with
352:IUPAC
2354:Halo
1839:Acyl
1739:and
1697:Aryl
1514:PMID
1479:PMID
1428:ISBN
1356:ISBN
1293:ISBN
1270:OCLC
1260:ISBN
1189:and
1134:and
1102:and
1082:are
1074:and
1003:and
969:zinc
887:and
819:(aq)
718:and
666:and
639:).
631:and
595:(PBr
541:SOCl
214:and
45:The
2005:Azo
1506:doi
1469:PMC
1461:doi
1420:doi
1348:doi
1323:doi
1252:doi
1219:As
956:, H
932:In
895:or
883:,
875:or
613:PBr
601:PBr
591:or
577:PCl
561:PCl
535:",
456:HBr
448:HCl
430:In
269:CCl
53:or
2520::
1737:,
1732:,
1520:.
1512:.
1502:33
1500:.
1477:.
1467:.
1457:58
1455:.
1451:.
1426:.
1378:.
1354:.
1319:31
1268:.
1258:.
1227:.
1138:.
1122:,
1118:,
1098:,
1094:,
1090:,
1054:,
1019:.
979:.
964:.
910:,
863:,
859:,
852:.
784:.
722:.
706:.
686:.
528:.
376:,
301:CF
285:CH
253:CI
210:,
206:,
194:,
190:,
181:Cl
172:CH
163:CH
117:.
105:.
85:,
81:,
77:,
73:,
1578:e
1571:t
1564:v
1528:.
1508::
1485:.
1463::
1436:.
1422::
1388:.
1364:.
1350::
1329:.
1325::
1301:.
1276:.
1254::
1174:.
1144:2
1106:.
958:2
912:N
618:3
606:3
597:3
582:3
575:(
566:5
559:(
546:2
539:(
487:2
479:2
454:(
446:(
306:4
299:(
290:4
283:(
274:4
267:(
258:4
251:(
177:2
168:3
161:(
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
