173:
261:
231:
202:
144:
290:
319:
838:
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).
421:
497:
1673:
1655:
1687:
1664:
1604:
1805:
1796:
1766:
1713:
1704:
1625:
1431:
1754:
1492:
1445:
1787:
1775:
1737:
1634:
1838:
1813:
1745:
1850:
1829:
1497:
1450:
1408:
1522:
1513:
1247:
725:
Dae Jin Sung; Dong Ju Moon; Yong Jun Lee; Suk-In Hong (2004). "Catalytic
Pyrolysis of Difluorochloromethane to Produce Tetrafluoroethylene".
678:
1128:
332:
Only chloroform has significant applications of the haloforms. In the predominant application, chloroform is required for the production of
872:
1165:
358:
1133:
427:
1070:"Associations between testicular hormones at adolescence and attendance at chlorinated swimming pools during childhood"
871:
EPA Alumni
Association: Senior EPA officials discuss early implementation of the Safe Drinking Water Act of 1974,
915:"Alveolar breath sampling and analysis to assess trihalomethane exposures during competitive swimming training"
856:
1898:
172:
1682:
260:
230:
1019:
Aiking, Harry; van Ackert, Manila B.; Schölten, Rob J.P.M.; Feenstra, Jan F.; Valkenburg, Hans A. (1994).
670:
Trihalomethanes were the subject of the first drinking water regulations issued after passage of the U.S.
1596:
1158:
1138:
876:
1139:
EPA - Trihalomethanes in
Drinking Water: Sampling, Analysis, Monitoring and Compliance (August 1983)
889:
1426:
659:
1584:
671:
532:
970:
Drobnic, Franchek; Freixa, Assumpci??; Casan, Pere; Sanchis, Joaqu??N; Guardino, Xavier (1996).
1646:
1613:
1559:
1903:
1893:
1873:
1695:
1567:
1417:
1392:
1151:
520:
345:
163:
1729:
1721:
1575:
1483:
1466:
1436:
1400:
769:
760:
Gribble, Gordon W. (2004). "Natural
Organohalogens: A New Frontier for Medicinal Agents?".
694:
690:
251:
221:
8:
1474:
1281:
333:
103:
773:
1858:
1551:
1320:
1290:
1102:
1069:
1025:
947:
914:
820:
742:
201:
143:
1821:
1329:
1299:
1107:
1089:
1085:
1050:
1042:
1038:
1020:
1001:
993:
988:
971:
952:
934:
852:
812:
698:
627:
536:
341:
289:
32:
824:
746:
1543:
1350:
1097:
1081:
1034:
983:
942:
926:
844:
804:
777:
734:
516:
318:
848:
662:
is one of the simplest possible stable chiral compounds, and is used for studies.
1308:
1269:
1203:
649:
561:
tonnes per year, and about 90% of emissions are natural in origin. Many kinds of
349:
348:(R-22). Pyrolysis of chlorodifluoromethane (at 550-750 °C) yields TFE, with
1338:
724:
83:
808:
1887:
1359:
1261:
1220:
1211:
1093:
1046:
997:
938:
554:
The total global flux of chloroform through the environment is approximately
1229:
1111:
816:
738:
1054:
1005:
956:
1238:
1174:
930:
524:
512:
59:
1458:
1384:
781:
705:
682:
631:
584:
508:
192:
131:
67:
1505:
686:
595:
280:
63:
20:
1530:
653:
606:
507:
Trihalomethanes released to the environment break down faster than
309:
50:
atoms. Trihalomethanes with all the same halogen atoms are called
1190:
1182:
645:
562:
543:
55:
47:
36:
1018:
630:, although this method does not lend itself to bulk syntheses. (
1143:
795:
Cappelletti, M. (2012). "Microbial degradation of chloroform".
681:
limits the total concentration of the four chief constituents (
337:
1129:
National
Pollutant Inventory - Chloroform and trichloromethane
972:"Assessment of chlorine exposure in swimmers during training"
837:
566:
136:
97:
528:
969:
475:
462:
446:
416:{\displaystyle {\ce {CHCl3 + 2 HF -> CHClF2 + 2 HCl}}}
399:
373:
697:), referred to as total trihalomethanes (TTHM), to 80
912:
727:
International
Journal of Chemical Reactor Engineering
430:
361:
1134:
How Ozone
Technology Reduces Disinfection Byproducts
16:
Methane (CH4) derivative with 3 halogen substituents
913:Lindstrom, A B; Pleil, J.D.; Berkoff, D.C. (1997).
492:{\displaystyle {\ce {2 CHClF2 -> C2F4 + 2 HCl}}}
491:
415:
73:
1067:
1885:
54:. Many trihalomethanes find uses in industry as
976:Medicine & Science in Sports & Exercise
1061:
1021:"Swimming pool chlorination: a health hazard?"
841:Ullmann's Encyclopedia of Industrial Chemistry
644:Chloroform is produced by heating mixtures of
511:(CFCs), thereby doing much less damage to the
1159:
340:. Chloroform is fluorinated by reaction with
35:in which three of the four hydrogen atoms of
906:
569:are believed to produce chloroform in soil.
549:
502:
794:
1166:
1152:
963:
1101:
1012:
987:
946:
527:. Chlorodifluoromethane is a refrigerant
484:
435:
408:
382:
890:"EPA | Envirofacts | ICR | Regulations"
759:
1886:
797:Applied Microbiology and Biotechnology
641:) cannot be prepared in this manner.)
1147:
539:. Fluoroform is not ozone depleting.
1068:Nickmilder, M.; Bernard, A. (2011).
62:. Some THMs are also environmental
13:
1074:International Journal of Andrology
656:. Dichloromethane is a coproduct.
327:
14:
1915:
1122:
919:Environmental Health Perspectives
535:, while fluoroform is an HFC, or
1173:
1086:10.1111/j.1365-2605.2011.01174.x
989:10.1097/00005768-199602000-00018
708:are produced in swimming pools.
626:are easy to prepare through the
317:
288:
259:
229:
200:
171:
142:
74:Table of common trihalomethanes
882:
865:
831:
788:
753:
718:
449:
386:
1:
849:10.1002/14356007.a06_233.pub2
762:Journal of Chemical Education
711:
665:
1039:10.1016/0378-4274(94)90051-5
839:"Chlorinated Hydrocarbons".
316:
287:
258:
228:
199:
170:
162:
141:
7:
256:chlorodibromomethane, CDBM
226:dichlorobromomethane, BDCM
66:, and a few are considered
10:
1920:
1870:
1542:
1375:
1260:
1202:
1181:
809:10.1007/s00253-012-4494-1
550:Occurrence and production
503:Refrigerants and solvents
197:R-20, methyl trichloride
660:Bromochlorofluoromethane
565:produce chloroform, and
672:Safe Drinking Water Act
542:Chloroform is a common
533:hydrochlorofluorocarbon
739:10.2202/1542-6580.1065
546:in organic chemistry.
493:
417:
157:chlorodifluoromethane
80:Common trihalomethanes
521:chlorodifluoromethane
494:
418:
346:chlorodifluoromethane
245:dibromochloromethane
215:bromodichloromethane
164:chlorodifluoromethane
1899:Halogenated solvents
931:10.1289/ehp.97105636
695:dibromochloromethane
691:bromodichloromethane
428:
359:
352:as an intermediate.
336:(TFE), precursor to
252:dibromochloromethane
222:bromodichloromethane
1080:(5pt2): e446–e458.
774:2004JChEd..81.1441G
509:chlorofluorocarbons
477:
464:
448:
401:
375:
334:tetrafluoroethylene
104:CAS registry number
87:
1026:Toxicology Letters
879:(see pages 12-13).
782:10.1021/ed081p1441
701:in treated water.
489:
465:
452:
436:
413:
389:
363:
285:methyl tribromide
78:
46:) are replaced by
33:chemical compounds
1881:
1880:
699:parts per billion
628:haloform reaction
537:hydrofluorocarbon
523:are both used as
487:
468:
455:
439:
411:
392:
385:
366:
342:hydrogen fluoride
325:
324:
314:methyl triiodide
186:trichloromethane
139:23, R-23, HFC-23
125:trifluoromethane
1911:
1544:Tetrasubstituted
1168:
1161:
1154:
1145:
1144:
1116:
1115:
1105:
1065:
1059:
1058:
1033:(1–3): 375–380.
1016:
1010:
1009:
991:
967:
961:
960:
950:
910:
904:
903:
901:
900:
886:
880:
869:
863:
862:
835:
829:
828:
792:
786:
785:
757:
751:
750:
722:
640:
625:
624:
620:
616:
604:
593:
582:
581:
577:
560:
559:
517:Trifluoromethane
498:
496:
495:
490:
488:
485:
476:
473:
466:
463:
460:
453:
447:
444:
437:
422:
420:
419:
414:
412:
409:
400:
397:
390:
383:
374:
371:
364:
321:
292:
274:tribromomethane
263:
233:
204:
175:
146:
88:
84:molecular weight
77:
45:
1919:
1918:
1914:
1913:
1912:
1910:
1909:
1908:
1884:
1883:
1882:
1877:
1866:
1862:
1854:
1846:
1842:
1833:
1825:
1817:
1809:
1800:
1791:
1783:
1779:
1770:
1762:
1758:
1749:
1741:
1733:
1725:
1717:
1708:
1699:
1691:
1677:
1668:
1659:
1650:
1642:
1638:
1629:
1621:
1617:
1608:
1600:
1592:
1588:
1579:
1571:
1563:
1555:
1538:
1534:
1526:
1517:
1509:
1501:
1487:
1478:
1470:
1462:
1454:
1440:
1421:
1412:
1404:
1396:
1388:
1371:
1367:
1363:
1354:
1346:
1342:
1333:
1324:
1316:
1312:
1303:
1294:
1285:
1277:
1273:
1256:
1251:
1242:
1233:
1224:
1215:
1204:Monosubstituted
1198:
1194:
1177:
1172:
1125:
1120:
1119:
1066:
1062:
1017:
1013:
968:
964:
911:
907:
898:
896:
894:archive.epa.gov
888:
887:
883:
870:
866:
859:
836:
832:
803:(6): 1395–409.
793:
789:
758:
754:
723:
719:
714:
668:
650:methyl chloride
639:
635:
622:
618:
615:
611:
609:
603:
599:
592:
588:
579:
575:
573:
557:
555:
552:
505:
474:
469:
461:
456:
445:
440:
431:
429:
426:
425:
398:
393:
372:
367:
362:
360:
357:
356:
350:difluorocarbene
330:
328:Industrial uses
303:triiodomethane
300:
271:
241:
212:
183:
154:
122:
76:
44:
40:
25:trihalomethanes
17:
12:
11:
5:
1917:
1907:
1906:
1901:
1896:
1879:
1878:
1871:
1868:
1867:
1865:
1864:
1860:
1856:
1852:
1848:
1844:
1840:
1836:
1831:
1827:
1823:
1819:
1815:
1811:
1807:
1803:
1798:
1794:
1789:
1785:
1781:
1777:
1773:
1768:
1764:
1760:
1756:
1752:
1747:
1743:
1739:
1735:
1731:
1727:
1723:
1719:
1715:
1711:
1706:
1702:
1697:
1693:
1689:
1685:
1680:
1675:
1671:
1666:
1662:
1657:
1653:
1648:
1644:
1640:
1636:
1632:
1627:
1623:
1619:
1615:
1611:
1606:
1602:
1598:
1594:
1590:
1586:
1582:
1577:
1573:
1569:
1565:
1561:
1557:
1553:
1548:
1546:
1540:
1539:
1537:
1536:
1532:
1528:
1524:
1520:
1515:
1511:
1507:
1503:
1499:
1495:
1490:
1485:
1481:
1476:
1472:
1468:
1464:
1460:
1456:
1452:
1448:
1443:
1438:
1434:
1429:
1424:
1419:
1415:
1410:
1406:
1402:
1398:
1394:
1390:
1386:
1381:
1379:
1377:Trisubstituted
1373:
1372:
1370:
1369:
1365:
1361:
1357:
1352:
1348:
1344:
1340:
1336:
1331:
1327:
1322:
1318:
1314:
1310:
1306:
1301:
1297:
1292:
1288:
1283:
1279:
1275:
1271:
1266:
1264:
1258:
1257:
1255:
1254:
1249:
1245:
1240:
1236:
1231:
1227:
1222:
1218:
1213:
1208:
1206:
1200:
1199:
1197:
1196:
1192:
1187:
1185:
1179:
1178:
1171:
1170:
1163:
1156:
1148:
1142:
1141:
1136:
1131:
1124:
1123:External links
1121:
1118:
1117:
1060:
1011:
982:(2): 271–274.
962:
925:(6): 636–642.
905:
881:
864:
857:
830:
787:
752:
716:
715:
713:
710:
667:
664:
637:
613:
601:
590:
583:specifically,
551:
548:
504:
501:
500:
499:
483:
480:
472:
459:
451:
443:
434:
423:
407:
404:
396:
388:
381:
378:
370:
329:
326:
323:
322:
315:
312:
307:
304:
301:
298:
294:
293:
286:
283:
278:
275:
272:
269:
265:
264:
257:
254:
249:
246:
243:
239:
235:
234:
227:
224:
219:
216:
213:
210:
206:
205:
198:
195:
190:
187:
184:
181:
177:
176:
169:
168:R-22, HCFC-22
166:
161:
158:
155:
152:
148:
147:
140:
134:
129:
126:
123:
120:
116:
115:
112:
109:
106:
101:
95:
75:
72:
42:
15:
9:
6:
4:
3:
2:
1916:
1905:
1902:
1900:
1897:
1895:
1892:
1891:
1889:
1875:
1869:
1863:
1857:
1855:
1849:
1847:
1837:
1835:
1828:
1826:
1820:
1818:
1812:
1810:
1804:
1802:
1795:
1793:
1786:
1784:
1774:
1772:
1765:
1763:
1753:
1751:
1744:
1742:
1736:
1734:
1728:
1726:
1720:
1718:
1712:
1710:
1703:
1701:
1694:
1692:
1686:
1684:
1681:
1679:
1672:
1670:
1663:
1661:
1654:
1652:
1645:
1643:
1633:
1631:
1624:
1622:
1612:
1610:
1603:
1601:
1595:
1593:
1583:
1581:
1574:
1572:
1566:
1564:
1558:
1556:
1550:
1549:
1547:
1545:
1541:
1535:
1529:
1527:
1521:
1519:
1512:
1510:
1504:
1502:
1496:
1494:
1491:
1489:
1482:
1480:
1473:
1471:
1465:
1463:
1457:
1455:
1449:
1447:
1444:
1442:
1435:
1433:
1430:
1428:
1425:
1423:
1416:
1414:
1407:
1405:
1399:
1397:
1391:
1389:
1383:
1382:
1380:
1378:
1374:
1368:
1358:
1356:
1349:
1347:
1337:
1335:
1328:
1326:
1319:
1317:
1307:
1305:
1298:
1296:
1289:
1287:
1280:
1278:
1268:
1267:
1265:
1263:
1262:Disubstituted
1259:
1253:
1246:
1244:
1237:
1235:
1228:
1226:
1219:
1217:
1210:
1209:
1207:
1205:
1201:
1195:
1189:
1188:
1186:
1184:
1183:Unsubstituted
1180:
1176:
1169:
1164:
1162:
1157:
1155:
1150:
1149:
1146:
1140:
1137:
1135:
1132:
1130:
1127:
1126:
1113:
1109:
1104:
1099:
1095:
1091:
1087:
1083:
1079:
1075:
1071:
1064:
1056:
1052:
1048:
1044:
1040:
1036:
1032:
1028:
1027:
1022:
1015:
1007:
1003:
999:
995:
990:
985:
981:
977:
973:
966:
958:
954:
949:
944:
940:
936:
932:
928:
924:
920:
916:
909:
895:
891:
885:
878:
874:
868:
860:
854:
850:
846:
842:
834:
826:
822:
818:
814:
810:
806:
802:
798:
791:
783:
779:
775:
771:
767:
763:
756:
748:
744:
740:
736:
732:
728:
721:
717:
709:
707:
702:
700:
696:
692:
688:
684:
680:
675:
673:
663:
661:
657:
655:
651:
647:
642:
633:
629:
608:
597:
586:
570:
568:
564:
547:
545:
540:
538:
534:
530:
526:
522:
518:
514:
510:
481:
478:
470:
457:
441:
432:
424:
405:
402:
394:
379:
376:
368:
355:
354:
353:
351:
347:
343:
339:
335:
320:
313:
311:
308:
305:
302:
296:
295:
291:
284:
282:
279:
276:
273:
267:
266:
262:
255:
253:
250:
247:
244:
237:
236:
232:
225:
223:
220:
217:
214:
208:
207:
203:
196:
194:
191:
188:
185:
179:
178:
174:
167:
165:
159:
156:
150:
149:
145:
138:
135:
133:
130:
127:
124:
118:
117:
113:
110:
107:
105:
102:
99:
96:
94:
90:
89:
85:
81:
71:
69:
65:
61:
57:
53:
49:
38:
34:
30:
26:
22:
1904:Refrigerants
1894:Halomethanes
1376:
1175:Halomethanes
1077:
1073:
1063:
1030:
1024:
1014:
979:
975:
965:
922:
918:
908:
897:. Retrieved
893:
884:
867:
840:
833:
800:
796:
790:
768:(10): 1441.
765:
761:
755:
730:
726:
720:
703:
676:
669:
658:
643:
572:Most of the
571:
553:
541:
525:refrigerants
506:
331:
111:Other names
108:Common name
92:
82:(ordered by
79:
68:carcinogenic
60:refrigerants
51:
28:
24:
18:
513:ozone layer
344:to produce
1888:Categories
899:2021-10-11
877:Transcript
858:3527306730
712:References
706:chloroform
704:Traces of
683:chloroform
666:Regulation
632:Fluoroform
585:chloroform
193:chloroform
132:fluoroform
91:Molecular
64:pollutants
1876:compound.
1094:0105-6263
1047:0378-4274
998:0195-9131
939:0091-6765
687:bromoform
674:in 1974.
596:bromoform
574:haloforms
450:⟶
387:⟶
281:bromoform
248:124-48-1
114:Molecule
52:haloforms
21:chemistry
1683:C*BrClFI
1493:C*HBrClI
1427:C*HBrClF
1112:21631527
825:12429523
817:23093177
747:97895482
654:chlorine
607:iodoform
310:iodoform
306:75-47-8
277:75-25-2
218:75-27-4
189:67-66-3
160:75-45-6
128:75-46-7
93:formula
56:solvents
1446:C*HBrFI
1432:C*HClFI
1103:3229674
1055:7911264
1006:8775165
957:9288498
948:1470079
770:Bibcode
646:methane
623:
619:
605:), and
580:
576:
563:seaweed
544:solvent
48:halogen
37:methane
31:s) are
1874:Chiral
1806:CBrClI
1597:CBrClF
1467:CHBrCl
1110:
1100:
1092:
1053:
1045:
1004:
996:
955:
945:
937:
855:
823:
815:
745:
733:: A6.
693:, and
338:teflon
209:CHBrCl
1767:CBrCl
1738:CBrCl
1714:CBrFI
1688:CClFI
1656:CBrCl
1523:CHBrI
1498:CHClI
1401:CHBrF
1393:CHClF
873:Video
821:S2CID
743:S2CID
652:with
567:fungi
531:, or
438:CHClF
391:CHClF
151:CHClF
137:Freon
100:name
98:IUPAC
1851:CBrI
1814:CClI
1626:CBrF
1605:CClF
1568:CBrF
1560:CClF
1514:CHBr
1506:CHBr
1484:CHBr
1475:CHCl
1459:CHCl
1451:CHFI
1437:CHBr
1418:CHCl
1325:BrCl
1108:PMID
1090:ISSN
1051:PMID
1043:ISSN
1002:PMID
994:ISSN
953:PMID
935:ISSN
853:ISBN
813:PMID
677:The
600:CHBr
589:CHCl
529:HCFC
519:and
365:CHCl
268:CHBr
238:CHBr
180:CHCl
1839:CBr
1830:CBr
1822:CBr
1801:ClI
1797:CBr
1788:CBr
1776:CCl
1755:CBr
1746:CCl
1730:CCl
1722:CFI
1705:CBr
1696:CBr
1678:ClF
1674:CBr
1665:CCl
1647:CCl
1614:CBr
1585:CCl
1531:CHI
1409:CHF
1385:CHF
1355:BrI
1334:ClI
1295:BrF
1286:ClF
1098:PMC
1082:doi
1035:doi
984:doi
943:PMC
927:doi
923:105
845:doi
805:doi
778:doi
735:doi
679:EPA
648:or
636:CHF
612:CHI
594:),
558:000
556:660
486:HCl
410:HCl
297:CHI
242:Cl
119:CHF
58:or
29:THM
19:In
1890::
1872:*
1859:CI
1792:Cl
1759:Cl
1709:FI
1669:FI
1635:CF
1576:CF
1552:CF
1488:Cl
1360:CH
1351:CH
1343:Br
1339:CH
1330:CH
1321:CH
1313:Cl
1309:CH
1304:FI
1300:CH
1291:CH
1282:CH
1270:CH
1252:At
1248:CH
1239:CH
1234:Br
1230:CH
1225:Cl
1221:CH
1212:CH
1191:CH
1106:.
1096:.
1088:.
1078:34
1076:.
1072:.
1049:.
1041:.
1031:72
1029:.
1023:.
1000:.
992:.
980:28
978:.
974:.
951:.
941:.
933:.
921:.
917:.
892:.
875:,
851:.
843:.
819:.
811:.
801:96
799:.
776:.
766:81
764:.
741:.
729:.
689:,
685:,
515:.
384:HF
86:)
70:.
41:CH
23:,
1861:4
1853:3
1845:2
1843:I
1841:2
1834:I
1832:3
1824:4
1816:3
1808:2
1799:2
1790:3
1782:2
1780:I
1778:2
1771:I
1769:2
1761:2
1757:2
1750:I
1748:3
1740:3
1732:4
1724:3
1716:2
1707:2
1700:F
1698:3
1690:2
1676:2
1667:2
1660:F
1658:2
1651:F
1649:3
1641:2
1639:I
1637:2
1630:I
1628:2
1620:2
1618:F
1616:2
1609:I
1607:2
1599:2
1591:2
1589:F
1587:2
1580:I
1578:3
1570:3
1562:3
1554:4
1533:3
1525:2
1518:I
1516:2
1508:3
1500:2
1486:2
1479:I
1477:2
1469:2
1461:3
1453:2
1441:F
1439:2
1422:F
1420:2
1413:I
1411:2
1403:2
1395:2
1387:3
1366:2
1364:I
1362:2
1353:2
1345:2
1341:2
1332:2
1323:2
1315:2
1311:2
1302:2
1293:2
1284:2
1276:2
1274:F
1272:2
1250:3
1243:I
1241:3
1232:3
1223:3
1216:F
1214:3
1193:4
1167:e
1160:t
1153:v
1114:.
1084::
1057:.
1037::
1008:.
986::
959:.
929::
902:.
861:.
847::
827:.
807::
784:.
780::
772::
749:.
737::
731:2
638:3
634:(
621:—
617:)
614:3
610:(
602:3
598:(
591:3
587:(
578:—
482:2
479:+
471:4
467:F
458:2
454:C
442:2
433:2
406:2
403:+
395:2
380:2
377:+
369:3
299:3
270:3
240:2
211:2
182:3
153:2
121:3
43:4
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