376:
240:
44:
1511:
53:
770:
765:
760:
945:
950:
1127:
949:
948:
778:
740:
876:
868:
1549:
1140:
1617:
951:
1877:
425:
1785:
872:
973:
1776:
1545:
1581:
Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "498. The dissociation constants of some symmetrically disubstituted succinic acids".
689:
1552:(42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
1440:
1634:
966:
1651:"Recherches sur les produits dérivés de l'éther acétique par l'action du chlore, et en particulier sur l'éther acétique perchloruré"
1448:
390:
1444:
721:
1817:
852:
1243:
in the presence of sunlight, and in 1857 (in pure form) by the German chemist
Reinhold Hoffmann (1831–1919) by refluxing
856:
822:
333:
769:
354:
916:
1778:
40 C.F.R.: Appendix A to Part 355—The List of
Extremely Hazardous Substances and Their Threshold Planning Quantities
959:
52:
1867:
1147:
1101:
592:
43:
247:
1872:
996:
1425:
1182:
888:
860:
611:
759:
235:
1096:
1091:
1671:
1650:
1862:
1692:
1460:
1264:
1256:
1164:
792:
764:
752:
569:
197:
77:
904:
1789:
1321:
1221:
1106:
1066:
880:
65:
1317:
1233:
1217:
1061:
840:
371:
105:
139:
1531:
1519:
832:
30:
828:
157:
1510:
1405:
released have led to the increased popularity of the halogenation route. Approximately 420,000
844:
1715:
1630:
1561:
1468:
1436:
1402:
1368:
1213:
1071:
1041:
1035:
653:
217:
1758:
1724:
1622:
1590:
1527:
1424:
In its largest-scale application, chloroacetic acid is used to prepare the thickening agent
1393:
The hydrolysis is conducted at 130–140 °C in a concentrated (at least 75%) solution of
1287:
1076:
628:
525:
448:
1837:
892:
342:
1491:
1487:
1429:
1278:
Chloroacetic acid is prepared industrially by two routes. The predominant method involves
1209:
1160:
1081:
896:
864:
884:
908:
375:
239:
177:
115:
1118:
806:
582:
1856:
1394:
670:
550:
514:
504:
228:
17:
924:
1398:
1325:
1237:
836:
1821:
848:
1523:
1283:
1244:
1240:
1086:
1023:
985:
306:
1499:
1464:
1456:
1452:
1260:
558:
536:
470:
208:
1762:
1728:
1626:
1476:
1232:
Chloroacetic acid was first prepared (in impure form) by the French chemist
814:
802:
1594:
1291:
1279:
1252:
1248:
1193:
1187:
972:
965:
958:
931:
542:
562:
554:
546:
494:
487:
293:
248:
1406:
1200:
1190:
188:
1117:
Except where otherwise noted, data are given for materials in their
1615:
Koenig, G.; Lohmar, E.; Rupprich, N. (2005). "Chloroacetic Acids".
281:
274:
1509:
1495:
798:
317:
168:
138:
128:
912:
1538:
920:
810:
265:
1472:
1451:(2,4,5-T) are produced. It is the precursor to the herbicide
1695:(in French) (Note on aldehyde and on acetyl chloride),
1417:
Most reactions take advantage of the high reactivity of the
900:
359:
1548:
in the United States as defined in
Section 302 of the U.S.
1482:
Illustrative of its usefulness in organic chemistry is the
1467:(epinephrine). Displacement of chloride by sulfide gives
1397:. This method produces a highly pure product, unlike the
943:
1713:
Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone".
1135:
1435:
Chloroacetic acid is also used in the production of
1693:"Note sur l'aldéhyde et sur le chlorure d'acétyle"
1661: : 197–221 ; see especially p. 212.
1550:Emergency Planning and Community Right-to-Know Act
1439:by etherification with chlorophenols. In this way
1324:as impurities, which are difficult to separate by
1216:. It is a colorless solid. Related compounds are
156:
305:
1749:Inglis, J. K. H. (1928). "Ethyl Cyanoacetate".
947:
114:
1674:(in German) (On mono-chloroacetic acid),
1618:Ullmann's Encyclopedia of Industrial Chemistry
1401:route. However, the significant quantities of
8:
519:189.3 °C (372.7 °F; 462.4 K)
1316:This route suffers from the production of
374:
238:
216:
35:
1610:
1608:
1606:
1604:
399:InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
341:
1385:
1381:
1377:
1367:The second method entails hydrolysis of
1359:
1355:
1351:
1342:
1338:
1334:
1308:
1304:
1300:
1270:
1203:
1196:
460:
456:
409:InChI=1/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
1573:
531:85.8 g/(100 mL) (25 °C)
430:
395:
370:
29:For chloroacetic acids in general, see
1004:470 °C (878 °F; 743 K)
990:126 °C (259 °F; 399 K)
229:
1878:Organic compounds with 2 carbon atoms
509:63 °C (145 °F; 336 K)
402:Key: FOCAUTSVDIKZOP-UHFFFAOYSA-N
196:
176:
7:
1490:with chloroacetic acid, followed by
1459:. Chloroacetic acid is converted to
1526:, chloroacetic acid is a hazardous
1471:, which is used as a stabilizer in
1441:2-methyl-4-chlorophenoxyacetic acid
412:Key: FOCAUTSVDIKZOP-UHFFFAOYAR
296:
280:
273:
25:
1449:2,4,5-trichlorophenoxyacetic acid
1255:, and then by the French chemist
1697:Annales de chimie et de physique
1676:Annalen der Chemie und Pharmacie
1655:Annales de Chimie et de Physique
1409:are produced globally per year.
1125:
768:
763:
758:
51:
42:
1583:Journal of the Chemical Society
1121:(at 25 °C , 100 kPa).
1703: : 58–62, see p. 61.
1445:2,4-dichlorophenoxyacetic acid
1212:is a useful building block in
722:Occupational safety and health
1:
1546:extremely hazardous substance
1672:"Ueber Monochloressigsäure"
1012:or concentration (LD, LC):
1894:
1786:Government Printing Office
1737:, vol. 5, p. 251
1670:Hoffmann, Reinhold (1857)
1158:
1102:2,2-Dichloropropionic acid
28:
1115:
1047:
1008:
739:
719:
714:
663:
646:
441:
421:
386:
98:
88:
76:
64:
59:
50:
41:
1784:(1 July 2008 ed.),
1763:10.15227/orgsyn.008.0074
1729:10.15227/orgsyn.046.0028
1627:10.1002/14356007.a06_537
1475:and a component in some
1173:, industrially known as
1159:Not to be confused with
823:Precautionary statements
1838:"Monochloroacetic Acid"
1818:"Monochloroacetic Acid"
1621:. Weinheim: Wiley-VCH.
1544:It is classified as an
1514:Chloroacetic acid burns
1426:carboxymethyl cellulose
1236:(1813–1886) in 1843 by
1183:organochlorine compound
612:Magnetic susceptibility
1820:. CABB. Archived from
1691:Wurtz, Adolphe (1857)
1649:LeBlanc, Félix (1844)
1515:
1097:3-Chloropropanoic acid
1092:2-Chloropropionic acid
954:
1513:
1461:chloroacetyl chloride
1265:chloroacetyl chloride
1257:Charles Adolphe Wurtz
1175:monochloroacetic acid
1165:Chloroacetyl chloride
953:
93:2-Chloroethanoic acid
78:Systematic IUPAC name
18:Monochloroacetic acid
1595:10.1039/JR9590002492
1430:carboxymethyl starch
1322:trichloroacetic acid
1222:trichloroacetic acid
1107:Sodium chloroacetate
1067:Trichloroacetic acid
936:(fire diamond)
642:1.4351 (55 °C)
66:Preferred IUPAC name
1795:on 25 February 2012
1318:dichloroacetic acid
1247:in the presence of
1245:glacial acetic acid
1218:dichloroacetic acid
1062:Dichloroacetic acid
526:Solubility in water
486:Colorless or white
478: g·mol
91:2-Chloroacetic acid
82:Chloroethanoic acid
38:
1824:on 6 February 2015
1653:(in French),
1541:is 76 mg/kg.
1520:chloroacetic acids
1516:
1437:phenoxy herbicides
1413:Uses and reactions
1148:Infobox references
1048:Related compounds
955:
37:Chloroacetic acid
36:
31:Chloroacetic acids
1868:Alkylating agents
1751:Organic Syntheses
1735:Collected Volumes
1716:Organic Syntheses
1562:Fluoroacetic acid
1494:of the resulting
1469:thioglycolic acid
1463:, a precursor to
1369:trichloroethylene
1275:), also in 1857.
1214:organic synthesis
1185:with the formula
1171:Chloroacetic acid
1156:Chemical compound
1154:
1153:
1072:Fluoroacetic acid
1054:Related compounds
1036:Safety data sheet
793:Hazard statements
735:alkylating agent
683:144.02 J/(K·mol)
654:Crystal structure
355:CompTox Dashboard
140:Interactive image
70:Chloroacetic acid
16:(Redirected from
1885:
1849:
1847:
1845:
1833:
1831:
1829:
1804:
1803:
1802:
1800:
1794:
1788:, archived from
1783:
1773:
1767:
1766:
1746:
1740:
1738:
1731:
1710:
1704:
1689:
1683:
1682:(1) : 1–20.
1668:
1662:
1647:
1641:
1640:
1612:
1599:
1598:
1578:
1528:alkylating agent
1420:
1389:
1363:
1346:
1312:
1288:acetic anhydride
1274:
1207:
1138:
1132:
1129:
1128:
1077:Bromoacetic acid
975:
968:
961:
946:
926:
922:
918:
914:
910:
906:
902:
898:
894:
890:
886:
882:
878:
874:
870:
866:
862:
858:
854:
850:
846:
842:
838:
834:
830:
816:
812:
808:
804:
800:
772:
767:
762:
706:
679:
664:Thermochemistry
629:Refractive index
621:
477:
464:
449:Chemical formula
379:
378:
363:
361:
345:
309:
298:
284:
277:
250:
242:
231:
220:
200:
180:
160:
142:
118:
55:
46:
39:
21:
1893:
1892:
1888:
1887:
1886:
1884:
1883:
1882:
1873:Organochlorides
1853:
1852:
1843:
1841:
1836:
1827:
1825:
1816:
1813:
1808:
1807:
1798:
1796:
1792:
1781:
1775:
1774:
1770:
1748:
1747:
1743:
1733:
1712:
1711:
1707:
1690:
1686:
1669:
1665:
1648:
1644:
1637:
1614:
1613:
1602:
1580:
1579:
1575:
1570:
1558:
1535:
1508:
1492:decarboxylation
1488:salicylaldehyde
1486:-alkylation of
1418:
1415:
1387:
1383:
1379:
1375:
1361:
1357:
1353:
1349:
1345:HC−COOH + 2 HCl
1344:
1340:
1336:
1332:
1310:
1306:
1302:
1298:
1272:
1268:
1230:
1210:carboxylic acid
1205:
1198:
1186:
1168:
1161:Acetyl chloride
1157:
1150:
1145:
1144:
1143: ?)
1134:
1130:
1126:
1122:
1111:
1082:Iodoacetic acid
1055:
1030:76 mg/kg.
1027:
1021:
1001:
998:
980:
979:
978:
977:
970:
963:
956:
952:
944:
825:
795:
781:
755:
732:
707:
704:
698:
694:
691:
690:Std enthalpy of
680:
673:
656:
639:
637:
619:
615:
601:
528:
499:1.58 g/cm
475:
462:
458:
454:
451:
437:
434:
429:
428:
417:
414:
413:
410:
404:
403:
400:
394:
393:
382:
364:
357:
348:
328:
312:
299:
287:
260:
223:
203:
183:
163:
145:
132:
121:
108:
94:
92:
84:
83:
72:
71:
34:
23:
22:
15:
12:
11:
5:
1891:
1889:
1881:
1880:
1875:
1870:
1865:
1855:
1854:
1851:
1850:
1834:
1812:
1811:External links
1809:
1806:
1805:
1768:
1741:
1705:
1699:, 3rd series,
1684:
1663:
1657:, 3rd series,
1642:
1636:978-3527306732
1635:
1600:
1572:
1571:
1569:
1566:
1565:
1564:
1557:
1554:
1533:
1507:
1504:
1414:
1411:
1391:
1390:
1388:C−COOH + 2 HCl
1365:
1364:
1362:C−COOH + 3 HCl
1347:
1314:
1313:
1229:
1226:
1155:
1152:
1151:
1146:
1124:
1123:
1119:standard state
1116:
1113:
1112:
1110:
1109:
1104:
1099:
1094:
1089:
1084:
1079:
1074:
1069:
1064:
1058:
1056:
1053:
1050:
1049:
1045:
1044:
1039:
1032:
1031:
1028:
1019:
1017:
1014:
1013:
1006:
1005:
1002:
995:
992:
991:
988:
982:
981:
971:
964:
957:
942:
941:
940:
939:
937:
928:
927:
877:P305+P351+P338
869:P303+P361+P353
861:P301+P330+P331
826:
821:
818:
817:
796:
791:
788:
787:
782:
777:
774:
773:
756:
751:
748:
747:
737:
736:
733:
730:
727:
726:
717:
716:
712:
711:
710:−490.1 kJ/mol
708:
702:
696:
688:
685:
684:
681:
669:
666:
665:
661:
660:
657:
652:
649:
648:
644:
643:
640:
635:
627:
624:
623:
616:
610:
607:
606:
603:
599:
589:
588:
585:
583:Vapor pressure
579:
578:
575:
566:
565:
539:
533:
532:
529:
524:
521:
520:
517:
511:
510:
507:
501:
500:
497:
491:
490:
484:
480:
479:
473:
467:
466:
452:
447:
444:
443:
439:
438:
436:
435:
432:
424:
423:
422:
419:
418:
416:
415:
411:
408:
407:
405:
401:
398:
397:
389:
388:
387:
384:
383:
381:
380:
367:
365:
353:
350:
349:
347:
346:
338:
336:
330:
329:
327:
326:
322:
320:
314:
313:
311:
310:
302:
300:
292:
289:
288:
286:
285:
278:
270:
268:
262:
261:
259:
258:
254:
252:
244:
243:
233:
225:
224:
222:
221:
213:
211:
205:
204:
202:
201:
193:
191:
185:
184:
182:
181:
173:
171:
165:
164:
162:
161:
153:
151:
147:
146:
144:
143:
135:
133:
126:
123:
122:
120:
119:
111:
109:
104:
101:
100:
96:
95:
90:
86:
85:
81:
80:
74:
73:
69:
68:
62:
61:
57:
56:
48:
47:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1890:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1860:
1858:
1840:. IPCS Inchem
1839:
1835:
1823:
1819:
1815:
1814:
1810:
1791:
1787:
1780:
1779:
1772:
1769:
1764:
1760:
1756:
1752:
1745:
1742:
1736:
1730:
1726:
1722:
1718:
1717:
1709:
1706:
1702:
1698:
1694:
1688:
1685:
1681:
1677:
1673:
1667:
1664:
1660:
1656:
1652:
1646:
1643:
1638:
1632:
1628:
1624:
1620:
1619:
1611:
1609:
1607:
1605:
1601:
1596:
1592:
1589:: 2492–2498.
1588:
1584:
1577:
1574:
1567:
1563:
1560:
1559:
1555:
1553:
1551:
1547:
1542:
1540:
1536:
1529:
1525:
1521:
1512:
1505:
1503:
1501:
1497:
1493:
1489:
1485:
1480:
1478:
1474:
1470:
1466:
1462:
1458:
1454:
1450:
1446:
1442:
1438:
1433:
1431:
1427:
1422:
1412:
1410:
1408:
1404:
1400:
1396:
1395:sulfuric acid
1374:
1373:
1372:
1370:
1354:C−COOH + 3 Cl
1348:
1337:C−COOH + 2 Cl
1331:
1330:
1329:
1327:
1323:
1319:
1297:
1296:
1295:
1293:
1289:
1285:
1281:
1276:
1266:
1262:
1258:
1254:
1250:
1246:
1242:
1239:
1235:
1234:Félix LeBlanc
1227:
1225:
1223:
1219:
1215:
1211:
1202:
1195:
1192:
1189:
1184:
1180:
1176:
1172:
1166:
1162:
1149:
1142:
1137:
1120:
1114:
1108:
1105:
1103:
1100:
1098:
1095:
1093:
1090:
1088:
1085:
1083:
1080:
1078:
1075:
1073:
1070:
1068:
1065:
1063:
1060:
1059:
1057:
1052:
1051:
1046:
1043:
1042:External MSDS
1040:
1037:
1034:
1033:
1029:
1025:
1016:
1015:
1011:
1007:
1003:
1000:
994:
993:
989:
987:
984:
983:
976:
969:
962:
938:
935:
934:
930:
929:
827:
824:
820:
819:
797:
794:
790:
789:
786:
783:
780:
776:
775:
771:
766:
761:
757:
754:
750:
749:
745:
743:
738:
734:
729:
728:
724:
723:
718:
713:
709:
701:
693:
687:
686:
682:
677:
672:
671:Heat capacity
668:
667:
662:
658:
655:
651:
650:
645:
641:
634:
630:
626:
625:
617:
613:
609:
608:
604:
598:
594:
591:
590:
586:
584:
581:
580:
576:
574:
573:
568:
567:
564:
560:
556:
552:
551:diethyl ether
548:
544:
540:
538:
535:
534:
530:
527:
523:
522:
518:
516:
515:Boiling point
513:
512:
508:
506:
505:Melting point
503:
502:
498:
496:
493:
492:
489:
485:
482:
481:
474:
472:
469:
468:
453:
450:
446:
445:
440:
431:
427:
420:
406:
396:
392:
385:
377:
373:
372:DTXSID4020901
369:
368:
366:
356:
352:
351:
344:
340:
339:
337:
335:
332:
331:
324:
323:
321:
319:
316:
315:
308:
304:
303:
301:
295:
291:
290:
283:
279:
276:
272:
271:
269:
267:
264:
263:
256:
255:
253:
251:
246:
245:
241:
237:
234:
232:
230:ECHA InfoCard
227:
226:
219:
215:
214:
212:
210:
207:
206:
199:
195:
194:
192:
190:
187:
186:
179:
175:
174:
172:
170:
167:
166:
159:
155:
154:
152:
149:
148:
141:
137:
136:
134:
130:
125:
124:
117:
113:
112:
110:
107:
103:
102:
97:
87:
79:
75:
67:
63:
58:
54:
49:
45:
40:
32:
27:
19:
1863:Acetic acids
1842:. Retrieved
1826:. Retrieved
1822:the original
1797:, retrieved
1790:the original
1777:
1771:
1754:
1750:
1744:
1734:
1720:
1714:
1708:
1700:
1696:
1687:
1679:
1675:
1666:
1658:
1654:
1645:
1616:
1586:
1582:
1576:
1543:
1522:and related
1517:
1498:, producing
1483:
1481:
1434:
1423:
1416:
1399:halogenation
1392:
1366:
1326:distillation
1315:
1311:C−COOH + HCl
1280:chlorination
1277:
1238:chlorinating
1231:
1178:
1174:
1170:
1169:
1009:
997:Autoignition
932:
784:
741:
731:Main hazards
720:
699:
675:
632:
596:
571:
318:RTECS number
99:Identifiers
89:Other names
26:
1524:halocarbons
1518:Like other
1303:C−COOH + Cl
1284:acetic acid
1241:acetic acid
1087:Acetic acid
1024:median dose
1010:Lethal dose
999:temperature
986:Flash point
779:Signal word
725:(OHS/OSH):
659:Monoclinic
541:Soluble in
483:Appearance
442:Properties
236:100.001.072
198:ChEMBL14090
178:CHEBI:27869
1857:Categories
1828:6 February
1799:29 October
1568:References
1500:benzofuran
1465:adrenaline
1457:dimethoate
1453:glyphosate
1261:hydrolysis
1228:Production
1181:), is the
753:Pictograms
647:Structure
622:10 cm/mol
559:chloroform
537:Solubility
471:Molar mass
343:5GD84Y125G
209:ChemSpider
127:3D model (
106:CAS Number
1477:cosmetics
917:P403+P233
873:P304+P340
865:P302+P352
857:P301+P310
744:labelling
692:formation
587:0.22 hPa
433:ClCC(O)=O
325:AF8575000
257:201-178-4
249:EC Number
1556:See also
1443:(MCPA),
1376:ClHC=CCl
1292:catalyst
1253:sunlight
1249:chlorine
933:NFPA 704
715:Hazards
614:(χ)
543:methanol
488:crystals
218:10772140
1421:bond.
1384:O → ClH
1286:, with
1208:. This
1141:what is
1139: (
593:Acidity
563:ethanol
555:benzene
547:acetone
495:Density
465:
294:PubChem
116:79-11-8
1844:20 May
1757:: 74.
1723:: 28.
1633:
1530:. The
1506:Safety
1447:, and
1407:tonnes
1136:verify
1133:
1038:(SDS)
785:Danger
426:SMILES
282:C06755
275:D07677
189:ChEMBL
158:B02139
150:3DMet
60:Names
1793:(PDF)
1782:(PDF)
1496:ether
1380:+ 2 H
1307:→ ClH
1290:as a
618:−48.1
605:2.86
577:0.22
476:94.49
391:InChI
169:ChEBI
129:JSmol
1846:2007
1830:2015
1801:2011
1631:ISBN
1587:1959
1539:rats
1537:for
1455:and
1428:and
1419:C−Cl
1358:→ Cl
1341:→ Cl
1320:and
1273:COCl
1269:ClCH
1251:and
1220:and
925:P501
921:P405
913:P391
909:P363
905:P361
901:P330
897:P322
893:P321
889:P312
885:P311
881:P310
853:P280
849:P273
845:P271
841:P270
837:P264
833:P261
829:P260
815:H400
811:H331
807:H314
803:H311
799:H301
570:log
455:ClCH
334:UNII
266:KEGG
1759:doi
1725:doi
1680:102
1623:doi
1591:doi
1473:PVC
1403:HCl
1282:of
1263:of
1259:by
1179:MCA
1163:or
742:GHS
703:298
360:EPA
307:300
297:CID
1859::
1753:.
1739:..
1732:;
1721:46
1719:.
1701:49
1678:,
1659:10
1629:.
1603:^
1585:.
1534:50
1532:LD
1502:.
1479:.
1432:.
1371::
1328::
1294::
1224:.
1188:Cl
1020:50
1018:LD
923:,
919:,
915:,
911:,
907:,
903:,
899:,
895:,
891:,
887:,
883:,
879:,
875:,
871:,
867:,
863:,
859:,
855:,
851:,
847:,
843:,
839:,
835:,
831:,
813:,
809:,
805:,
801:,
746::
695:(Δ
602:)
595:(p
561:,
557:,
553:,
549:,
545:,
459:CO
1848:.
1832:.
1765:.
1761::
1755:8
1727::
1639:.
1625::
1597:.
1593::
1484:O
1386:2
1382:2
1378:2
1360:3
1356:2
1352:3
1350:H
1343:2
1339:2
1335:3
1333:H
1309:2
1305:2
1301:3
1299:H
1271:2
1267:(
1206:H
1204:2
1201:O
1199:C
1197:2
1194:H
1191:C
1177:(
1167:.
1131:N
1026:)
1022:(
974:0
967:1
960:3
705:)
700:H
697:f
678:)
676:C
674:(
638:)
636:D
633:n
631:(
620:×
600:a
597:K
572:P
463:H
461:2
457:2
362:)
358:(
131:)
33:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
