184:
272:
242:
213:
155:
301:
330:
849:
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).
432:
508:
689:
1176:
736:
Dae Jin Sung; Dong Ju Moon; Yong Jun Lee; Suk-In Hong (2004). "Catalytic
Pyrolysis of Difluorochloromethane to Produce Tetrafluoroethylene".
1139:
343:
Only chloroform has significant applications of the haloforms. In the predominant application, chloroform is required for the production of
883:
369:
867:
183:
1144:
271:
241:
1909:
1693:
438:
1081:"Associations between testicular hormones at adolescence and attendance at chlorinated swimming pools during childhood"
1607:
1169:
882:
EPA Alumni
Association: Senior EPA officials discuss early implementation of the Safe Drinking Water Act of 1974,
1684:
1666:
1698:
1675:
1615:
1437:
926:"Alveolar breath sampling and analysis to assess trihalomethane exposures during competitive swimming training"
670:
1816:
1807:
1777:
1724:
1715:
1636:
1442:
1765:
1595:
1503:
1456:
682:
543:
1798:
1786:
1748:
1645:
1849:
1824:
1756:
1657:
1624:
1570:
1030:
Aiking, Harry; van Ackert, Manila B.; Schölten, Rob J.P.M.; Feenstra, Jan F.; Valkenburg, Hans A. (1994).
681:
Trihalomethanes were the subject of the first drinking water regulations issued after passage of the U.S.
1861:
1840:
1508:
1461:
1419:
1914:
1904:
1884:
1706:
1578:
1533:
1524:
1428:
1403:
1162:
531:
356:
174:
1149:
887:
1740:
1732:
1586:
1494:
1477:
1447:
1411:
1258:
780:
705:
701:
262:
232:
1150:
EPA - Trihalomethanes in
Drinking Water: Sampling, Analysis, Monitoring and Compliance (August 1983)
900:
1485:
1292:
344:
212:
154:
114:
1869:
1562:
1331:
1301:
1036:
831:
753:
300:
981:
Drobnic, Franchek; Freixa, Assumpci??; Casan, Pere; Sanchis, Joaqu??N; Guardino, Xavier (1996).
329:
1832:
1340:
1310:
1118:
1100:
1061:
1053:
1012:
1004:
963:
945:
863:
823:
709:
638:
547:
352:
43:
1554:
1361:
1108:
1092:
1045:
994:
953:
937:
855:
815:
788:
745:
527:
771:
Gribble, Gordon W. (2004). "Natural
Organohalogens: A New Frontier for Medicinal Agents?".
1319:
1280:
1214:
660:
360:
784:
1349:
1113:
1080:
958:
925:
94:
1898:
1370:
1272:
1231:
1222:
1096:
1049:
1031:
999:
982:
835:
757:
1240:
859:
673:
is one of the simplest possible stable chiral compounds, and is used for studies.
572:
tonnes per year, and about 90% of emissions are natural in origin. Many kinds of
359:(R-22). Pyrolysis of chlorodifluoromethane (at 550-750 °C) yields TFE, with
1249:
1185:
535:
523:
70:
1469:
1395:
819:
716:
693:
642:
595:
519:
203:
142:
78:
1104:
1057:
1008:
949:
565:
The total global flux of chloroform through the environment is approximately
1516:
697:
606:
291:
74:
31:
1122:
827:
749:
1065:
1016:
967:
1541:
941:
664:
617:
320:
17:
1201:
1193:
792:
656:
573:
554:
66:
58:
47:
348:
518:
Trihalomethanes released to the environment break down faster than
577:
147:
108:
61:
atoms. Trihalomethanes with all the same halogen atoms are called
641:, although this method does not lend itself to bulk syntheses. (
539:
1158:
1154:
806:
Cappelletti, M. (2012). "Microbial degradation of chloroform".
692:
limits the total concentration of the four chief constituents (
1140:
National
Pollutant Inventory - Chloroform and trichloromethane
983:"Assessment of chlorine exposure in swimmers during training"
486:
473:
457:
427:{\displaystyle {\ce {CHCl3 + 2 HF -> CHClF2 + 2 HCl}}}
410:
384:
708:), referred to as total trihalomethanes (TTHM), to 80
738:
International
Journal of Chemical Reactor Engineering
441:
372:
1145:
How Ozone
Technology Reduces Disinfection Byproducts
27:
Methane (CH4) derivative with 3 halogen substituents
1553:
1386:
1271:
1213:
1192:
924:Lindstrom, A B; Pleil, J.D.; Berkoff, D.C. (1997).
503:{\displaystyle {\ce {2 CHClF2 -> C2F4 + 2 HCl}}}
502:
426:
65:. Many trihalomethanes find uses in industry as
987:Medicine & Science in Sports & Exercise
1032:"Swimming pool chlorination: a health hazard?"
852:Ullmann's Encyclopedia of Industrial Chemistry
655:Chloroform is produced by heating mixtures of
522:(CFCs), thereby doing much less damage to the
1170:
351:. Chloroform is fluorinated by reaction with
46:in which three of the four hydrogen atoms of
8:
580:are believed to produce chloroform in soil.
1177:
1163:
1155:
1112:
998:
957:
538:. Chlorodifluoromethane is a refrigerant
495:
485:
480:
472:
467:
456:
451:
446:
442:
440:
419:
409:
404:
393:
383:
378:
373:
371:
648:
624:
612:
601:
88:
53:
901:"EPA | Envirofacts | ICR | Regulations"
728:
808:Applied Microbiology and Biotechnology
652:) cannot be prepared in this manner.)
550:. Fluoroform is not ozone depleting.
7:
1079:Nickmilder, M.; Bernard, A. (2011).
73:. Some THMs are also environmental
1085:International Journal of Andrology
667:. Dichloromethane is a coproduct.
25:
930:Environmental Health Perspectives
546:, while fluoroform is an HFC, or
1097:10.1111/j.1365-2605.2011.01174.x
1000:10.1097/00005768-199602000-00018
719:are produced in swimming pools.
637:are easy to prepare through the
328:
299:
270:
240:
211:
182:
153:
85:Table of common trihalomethanes
460:
397:
1:
860:10.1002/14356007.a06_233.pub2
773:Journal of Chemical Education
1050:10.1016/0378-4274(94)90051-5
850:"Chlorinated Hydrocarbons".
327:
298:
269:
239:
210:
181:
173:
152:
267:chlorodibromomethane, CDBM
237:dichlorobromomethane, BDCM
77:, and a few are considered
1931:
1881:
820:10.1007/s00253-012-4494-1
561:Occurrence and production
514:Refrigerants and solvents
208:R-20, methyl trichloride
671:Bromochlorofluoromethane
576:produce chloroform, and
683:Safe Drinking Water Act
553:Chloroform is a common
544:hydrochlorofluorocarbon
750:10.2202/1542-6580.1065
557:in organic chemistry.
504:
428:
168:chlorodifluoromethane
91:Common trihalomethanes
532:chlorodifluoromethane
505:
429:
357:chlorodifluoromethane
256:dibromochloromethane
226:bromodichloromethane
175:chlorodifluoromethane
1910:Halogenated solvents
942:10.1289/ehp.97105636
706:dibromochloromethane
702:bromodichloromethane
439:
370:
363:as an intermediate.
347:(TFE), precursor to
263:dibromochloromethane
233:bromodichloromethane
1091:(5pt2): e446–e458.
785:2004JChEd..81.1441G
520:chlorofluorocarbons
488:
475:
459:
412:
386:
345:tetrafluoroethylene
115:CAS registry number
98:
1037:Toxicology Letters
890:(see pages 12-13).
793:10.1021/ed081p1441
712:in treated water.
500:
476:
463:
447:
424:
400:
374:
296:methyl tribromide
89:
57:) are replaced by
44:chemical compounds
1892:
1891:
710:parts per billion
639:haloform reaction
548:hydrofluorocarbon
534:are both used as
498:
479:
466:
450:
422:
403:
396:
377:
353:hydrogen fluoride
336:
335:
325:methyl triiodide
197:trichloromethane
150:23, R-23, HFC-23
136:trifluoromethane
16:(Redirected from
1922:
1555:Tetrasubstituted
1179:
1172:
1165:
1156:
1127:
1126:
1116:
1076:
1070:
1069:
1044:(1–3): 375–380.
1027:
1021:
1020:
1002:
978:
972:
971:
961:
921:
915:
914:
912:
911:
897:
891:
880:
874:
873:
846:
840:
839:
803:
797:
796:
768:
762:
761:
733:
651:
636:
635:
631:
627:
615:
604:
593:
592:
588:
571:
570:
528:Trifluoromethane
509:
507:
506:
501:
499:
496:
487:
484:
477:
474:
471:
464:
458:
455:
448:
433:
431:
430:
425:
423:
420:
411:
408:
401:
394:
385:
382:
375:
332:
303:
285:tribromomethane
274:
244:
215:
186:
157:
99:
95:molecular weight
56:
21:
1930:
1929:
1925:
1924:
1923:
1921:
1920:
1919:
1895:
1894:
1893:
1888:
1877:
1873:
1865:
1857:
1853:
1844:
1836:
1828:
1820:
1811:
1802:
1794:
1790:
1781:
1773:
1769:
1760:
1752:
1744:
1736:
1728:
1719:
1710:
1702:
1688:
1679:
1670:
1661:
1653:
1649:
1640:
1632:
1628:
1619:
1611:
1603:
1599:
1590:
1582:
1574:
1566:
1549:
1545:
1537:
1528:
1520:
1512:
1498:
1489:
1481:
1473:
1465:
1451:
1432:
1423:
1415:
1407:
1399:
1382:
1378:
1374:
1365:
1357:
1353:
1344:
1335:
1327:
1323:
1314:
1305:
1296:
1288:
1284:
1267:
1262:
1253:
1244:
1235:
1226:
1215:Monosubstituted
1209:
1205:
1188:
1183:
1136:
1131:
1130:
1078:
1077:
1073:
1029:
1028:
1024:
980:
979:
975:
923:
922:
918:
909:
907:
905:archive.epa.gov
899:
898:
894:
881:
877:
870:
848:
847:
843:
814:(6): 1395–409.
805:
804:
800:
770:
769:
765:
735:
734:
730:
725:
679:
661:methyl chloride
650:
646:
633:
629:
626:
622:
620:
614:
610:
603:
599:
590:
586:
584:
568:
566:
563:
516:
437:
436:
368:
367:
361:difluorocarbene
341:
339:Industrial uses
314:triiodomethane
311:
282:
252:
223:
194:
165:
133:
87:
55:
51:
36:trihalomethanes
28:
23:
22:
15:
12:
11:
5:
1928:
1926:
1918:
1917:
1912:
1907:
1897:
1896:
1890:
1889:
1882:
1879:
1878:
1876:
1875:
1871:
1867:
1863:
1859:
1855:
1851:
1847:
1842:
1838:
1834:
1830:
1826:
1822:
1818:
1814:
1809:
1805:
1800:
1796:
1792:
1788:
1784:
1779:
1775:
1771:
1767:
1763:
1758:
1754:
1750:
1746:
1742:
1738:
1734:
1730:
1726:
1722:
1717:
1713:
1708:
1704:
1700:
1696:
1691:
1686:
1682:
1677:
1673:
1668:
1664:
1659:
1655:
1651:
1647:
1643:
1638:
1634:
1630:
1626:
1622:
1617:
1613:
1609:
1605:
1601:
1597:
1593:
1588:
1584:
1580:
1576:
1572:
1568:
1564:
1559:
1557:
1551:
1550:
1548:
1547:
1543:
1539:
1535:
1531:
1526:
1522:
1518:
1514:
1510:
1506:
1501:
1496:
1492:
1487:
1483:
1479:
1475:
1471:
1467:
1463:
1459:
1454:
1449:
1445:
1440:
1435:
1430:
1426:
1421:
1417:
1413:
1409:
1405:
1401:
1397:
1392:
1390:
1388:Trisubstituted
1384:
1383:
1381:
1380:
1376:
1372:
1368:
1363:
1359:
1355:
1351:
1347:
1342:
1338:
1333:
1329:
1325:
1321:
1317:
1312:
1308:
1303:
1299:
1294:
1290:
1286:
1282:
1277:
1275:
1269:
1268:
1266:
1265:
1260:
1256:
1251:
1247:
1242:
1238:
1233:
1229:
1224:
1219:
1217:
1211:
1210:
1208:
1207:
1203:
1198:
1196:
1190:
1189:
1184:
1182:
1181:
1174:
1167:
1159:
1153:
1152:
1147:
1142:
1135:
1134:External links
1132:
1129:
1128:
1071:
1022:
993:(2): 271–274.
973:
936:(6): 636–642.
916:
892:
875:
868:
841:
798:
763:
727:
726:
724:
721:
678:
675:
594:specifically,
562:
559:
515:
512:
511:
510:
494:
491:
483:
470:
462:
454:
445:
434:
418:
415:
407:
399:
392:
389:
381:
340:
337:
334:
333:
326:
323:
318:
315:
312:
309:
305:
304:
297:
294:
289:
286:
283:
280:
276:
275:
268:
265:
260:
257:
254:
250:
246:
245:
238:
235:
230:
227:
224:
221:
217:
216:
209:
206:
201:
198:
195:
192:
188:
187:
180:
179:R-22, HCFC-22
177:
172:
169:
166:
163:
159:
158:
151:
145:
140:
137:
134:
131:
127:
126:
123:
120:
117:
112:
106:
86:
83:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1927:
1916:
1913:
1911:
1908:
1906:
1903:
1902:
1900:
1886:
1880:
1874:
1868:
1866:
1860:
1858:
1848:
1846:
1839:
1837:
1831:
1829:
1823:
1821:
1815:
1813:
1806:
1804:
1797:
1795:
1785:
1783:
1776:
1774:
1764:
1762:
1755:
1753:
1747:
1745:
1739:
1737:
1731:
1729:
1723:
1721:
1714:
1712:
1705:
1703:
1697:
1695:
1692:
1690:
1683:
1681:
1674:
1672:
1665:
1663:
1656:
1654:
1644:
1642:
1635:
1633:
1623:
1621:
1614:
1612:
1606:
1604:
1594:
1592:
1585:
1583:
1577:
1575:
1569:
1567:
1561:
1560:
1558:
1556:
1552:
1546:
1540:
1538:
1532:
1530:
1523:
1521:
1515:
1513:
1507:
1505:
1502:
1500:
1493:
1491:
1484:
1482:
1476:
1474:
1468:
1466:
1460:
1458:
1455:
1453:
1446:
1444:
1441:
1439:
1436:
1434:
1427:
1425:
1418:
1416:
1410:
1408:
1402:
1400:
1394:
1393:
1391:
1389:
1385:
1379:
1369:
1367:
1360:
1358:
1348:
1346:
1339:
1337:
1330:
1328:
1318:
1316:
1309:
1307:
1300:
1298:
1291:
1289:
1279:
1278:
1276:
1274:
1273:Disubstituted
1270:
1264:
1257:
1255:
1248:
1246:
1239:
1237:
1230:
1228:
1221:
1220:
1218:
1216:
1212:
1206:
1200:
1199:
1197:
1195:
1194:Unsubstituted
1191:
1187:
1180:
1175:
1173:
1168:
1166:
1161:
1160:
1157:
1151:
1148:
1146:
1143:
1141:
1138:
1137:
1133:
1124:
1120:
1115:
1110:
1106:
1102:
1098:
1094:
1090:
1086:
1082:
1075:
1072:
1067:
1063:
1059:
1055:
1051:
1047:
1043:
1039:
1038:
1033:
1026:
1023:
1018:
1014:
1010:
1006:
1001:
996:
992:
988:
984:
977:
974:
969:
965:
960:
955:
951:
947:
943:
939:
935:
931:
927:
920:
917:
906:
902:
896:
893:
889:
885:
879:
876:
871:
865:
861:
857:
853:
845:
842:
837:
833:
829:
825:
821:
817:
813:
809:
802:
799:
794:
790:
786:
782:
778:
774:
767:
764:
759:
755:
751:
747:
743:
739:
732:
729:
722:
720:
718:
713:
711:
707:
703:
699:
695:
691:
686:
684:
676:
674:
672:
668:
666:
662:
658:
653:
644:
640:
619:
608:
597:
581:
579:
575:
560:
558:
556:
551:
549:
545:
541:
537:
533:
529:
525:
521:
513:
492:
489:
481:
468:
452:
443:
435:
416:
413:
405:
390:
387:
379:
366:
365:
364:
362:
358:
354:
350:
346:
338:
331:
324:
322:
319:
316:
313:
307:
306:
302:
295:
293:
290:
287:
284:
278:
277:
273:
266:
264:
261:
258:
255:
248:
247:
243:
236:
234:
231:
228:
225:
219:
218:
214:
207:
205:
202:
199:
196:
190:
189:
185:
178:
176:
170:
167:
161:
160:
156:
149:
146:
144:
141:
138:
135:
129:
128:
124:
121:
118:
116:
113:
110:
107:
105:
101:
100:
96:
92:
84:
82:
80:
76:
72:
68:
64:
60:
49:
45:
41:
37:
33:
19:
1915:Refrigerants
1905:Halomethanes
1387:
1186:Halomethanes
1088:
1084:
1074:
1041:
1035:
1025:
990:
986:
976:
933:
929:
919:
908:. Retrieved
904:
895:
878:
851:
844:
811:
807:
801:
779:(10): 1441.
776:
772:
766:
741:
737:
731:
714:
687:
680:
669:
654:
583:Most of the
582:
564:
552:
536:refrigerants
517:
342:
122:Other names
119:Common name
103:
93:(ordered by
90:
79:carcinogenic
71:refrigerants
62:
39:
35:
29:
524:ozone layer
355:to produce
1899:Categories
910:2021-10-11
888:Transcript
869:3527306730
723:References
717:chloroform
715:Traces of
694:chloroform
677:Regulation
643:Fluoroform
596:chloroform
204:chloroform
143:fluoroform
102:Molecular
75:pollutants
1887:compound.
1105:0105-6263
1058:0378-4274
1009:0195-9131
950:0091-6765
698:bromoform
685:in 1974.
607:bromoform
585:haloforms
461:⟶
398:⟶
292:bromoform
259:124-48-1
125:Molecule
63:haloforms
32:chemistry
1694:C*BrClFI
1504:C*HBrClI
1438:C*HBrClF
1123:21631527
836:12429523
828:23093177
758:97895482
665:chlorine
618:iodoform
321:iodoform
317:75-47-8
288:75-25-2
229:75-27-4
200:67-66-3
171:75-45-6
139:75-46-7
104:formula
67:solvents
18:Haloform
1457:C*HBrFI
1443:C*HClFI
1114:3229674
1066:7911264
1017:8775165
968:9288498
959:1470079
781:Bibcode
657:methane
634:
630:
616:), and
591:
587:
574:seaweed
555:solvent
59:halogen
48:methane
42:s) are
1885:Chiral
1817:CBrClI
1608:CBrClF
1478:CHBrCl
1121:
1111:
1103:
1064:
1056:
1015:
1007:
966:
956:
948:
866:
834:
826:
756:
744:: A6.
704:, and
349:teflon
220:CHBrCl
1778:CBrCl
1749:CBrCl
1725:CBrFI
1699:CClFI
1667:CBrCl
1534:CHBrI
1509:CHClI
1412:CHBrF
1404:CHClF
884:Video
832:S2CID
754:S2CID
663:with
578:fungi
542:, or
449:CHClF
402:CHClF
162:CHClF
148:Freon
111:name
109:IUPAC
1862:CBrI
1825:CClI
1637:CBrF
1616:CClF
1579:CBrF
1571:CClF
1525:CHBr
1517:CHBr
1495:CHBr
1486:CHCl
1470:CHCl
1462:CHFI
1448:CHBr
1429:CHCl
1336:BrCl
1119:PMID
1101:ISSN
1062:PMID
1054:ISSN
1013:PMID
1005:ISSN
964:PMID
946:ISSN
864:ISBN
824:PMID
688:The
611:CHBr
600:CHCl
540:HCFC
530:and
376:CHCl
279:CHBr
249:CHBr
191:CHCl
1850:CBr
1841:CBr
1833:CBr
1812:ClI
1808:CBr
1799:CBr
1787:CCl
1766:CBr
1757:CCl
1741:CCl
1733:CFI
1716:CBr
1707:CBr
1689:ClF
1685:CBr
1676:CCl
1658:CCl
1625:CBr
1596:CCl
1542:CHI
1420:CHF
1396:CHF
1366:BrI
1345:ClI
1306:BrF
1297:ClF
1109:PMC
1093:doi
1046:doi
995:doi
954:PMC
938:doi
934:105
856:doi
816:doi
789:doi
746:doi
690:EPA
659:or
647:CHF
623:CHI
605:),
569:000
567:660
497:HCl
421:HCl
308:CHI
253:Cl
130:CHF
69:or
40:THM
30:In
1901::
1883:*
1870:CI
1803:Cl
1770:Cl
1720:FI
1680:FI
1646:CF
1587:CF
1563:CF
1499:Cl
1371:CH
1362:CH
1354:Br
1350:CH
1341:CH
1332:CH
1324:Cl
1320:CH
1315:FI
1311:CH
1302:CH
1293:CH
1281:CH
1263:At
1259:CH
1250:CH
1245:Br
1241:CH
1236:Cl
1232:CH
1223:CH
1202:CH
1117:.
1107:.
1099:.
1089:34
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1083:.
1060:.
1052:.
1042:72
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1034:.
1011:.
1003:.
991:28
989:.
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962:.
952:.
944:.
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903:.
886:,
862:.
854:.
830:.
822:.
812:96
810:.
787:.
777:81
775:.
752:.
740:.
700:,
696:,
526:.
395:HF
97:)
81:.
52:CH
34:,
1872:4
1864:3
1856:2
1854:I
1852:2
1845:I
1843:3
1835:4
1827:3
1819:2
1810:2
1801:3
1793:2
1791:I
1789:2
1782:I
1780:2
1772:2
1768:2
1761:I
1759:3
1751:3
1743:4
1735:3
1727:2
1718:2
1711:F
1709:3
1701:2
1687:2
1678:2
1671:F
1669:2
1662:F
1660:3
1652:2
1650:I
1648:2
1641:I
1639:2
1631:2
1629:F
1627:2
1620:I
1618:2
1610:2
1602:2
1600:F
1598:2
1591:I
1589:3
1581:3
1573:3
1565:4
1544:3
1536:2
1529:I
1527:2
1519:3
1511:2
1497:2
1490:I
1488:2
1480:2
1472:3
1464:2
1452:F
1450:2
1433:F
1431:2
1424:I
1422:2
1414:2
1406:2
1398:3
1377:2
1375:I
1373:2
1364:2
1356:2
1352:2
1343:2
1334:2
1326:2
1322:2
1313:2
1304:2
1295:2
1287:2
1285:F
1283:2
1261:3
1254:I
1252:3
1243:3
1234:3
1227:F
1225:3
1204:4
1178:e
1171:t
1164:v
1125:.
1095::
1068:.
1048::
1019:.
997::
970:.
940::
913:.
872:.
858::
838:.
818::
795:.
791::
783::
760:.
748::
742:2
649:3
645:(
632:—
628:)
625:3
621:(
613:3
609:(
602:3
598:(
589:—
493:2
490:+
482:4
478:F
469:2
465:C
453:2
444:2
417:2
414:+
406:2
391:2
388:+
380:3
310:3
281:3
251:2
222:2
193:3
164:2
132:3
54:4
50:(
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20:)
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