282:
189:
998:
517:
44:
978:
897:
35:
584:
525:
497:
1050:
Trityl derivatives of reactive functional groups are often crystalline and in some cases sterically stabilized relative to less bulky derivatives. Three such derivatives are
1312:
Glidewell, C.; Ferguson, G. (1994). "Molecules isoelectronic with 2,2,2-triphenylethanol: Multiple
Hydrogen-Bonding Modes in the Structures of O-Tritylhydroxylamine, Ph
1379:
597:
1184:
Xue, Xiao-Song; Ji, Pengju; Zhou, Biying; Cheng, Jin-Pei (2017). "The
Essential Role of Bond Energetics in C–H Activation/Functionalization".
647:
CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic
331:
880:
over three phenyl rings. Steric effects however prevent all three phenyl rings from achieving coplanarity simultaneously. Consequently
884:
is even more acidic, albeit only slightly, because in its anion the charge is spread over two phenyl rings at the same time.
592:
863:(BDE) of 81 kcal/mol, or about 24 kcal/mol less than methane. Correspondingly, triphenylmethane is mildly acidic, with a
1097:
126:
296:
604:
566:
1369:
1136:
1051:
1014:
The triphenylmethyl substituent, also called trityl, is widely used in organic chemistry. Trityl serves as a
239:
184:
735:
260:
1122:
516:
457:
1374:
196:
997:
1092:
904:
860:
844:
782:
672:
277:
1102:
951:
876:
Triphenylmethane is significantly more acidic than most other hydrocarbons because the charge is
676:
476:
17:
977:
940:
539:
509:
1337:
836:
778:
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56:
8:
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969:
560:
1345:
1294:
1235:
1193:
1166:
1015:
632:
432:
354:
688:
305:
InChI=1S/C19H16/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
228:
989:
881:
712:
692:
315:
InChI=1/C19H16/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
1254:
1197:
877:
575:
1349:
691:
and his Dutch student
Antoine Paul Nicolas Franchimont (1844–1919) by heating
1363:
1298:
1170:
421:
411:
177:
43:
1219:
Ronald
Breslow and William Chu (1969). "Electrochemical determinations of p
1205:
944:
840:
660:
656:
888:
628:
449:
1280:
1239:
896:
743:
443:
376:
197:
157:
687:
Triphenylmethane was first synthesized in 1872 by the German chemist
574:
Except where otherwise noted, data are given for materials in their
985:
750:
125:
34:
1330:
1252:
739:
397:
215:
950:
The unmodified anion is red, and can be used as an indicator in
1218:
553:
137:
115:
265:
954:. Derived substances have proven useful as chemical dyes.
549:
1045:
864:
648:
416:
92 to 94 °C (198 to 201 °F; 365 to 367 K)
667:
group in organic chemistry is a triphenylmethyl group Ph
1281:
Delbert D. Reynolds, William Lloyd Evans (1942). "β-
545:
1311:
1361:
227:
101:
1183:
1141:Berichte der deutschen chemischen Gesellschaft
789:adduct, which is hydrolyzed with dilute acid:
1226:'s. Triphenylmethanes and cycloheptatriene".
1156:
943:has been eclipsed by the popularization of
1253:W. B. Renfrow Jr and C. R. Hauser (1943).
895:
280:
187:
165:
1380:Substances discovered in the 19th century
1157:J. F. Norris (1925). "Triphenylmethane".
1022:protection (requires proton acceptor): Ph
247:
1228:Journal of the American Chemical Society
850:
734:Triphenylmethane can be synthesized by
276:
14:
1362:
1135:Aug. Kekulé and A. Franchimont (1872)
1046:Platform for unusual functional groups
957:
781:using the same catalyst to obtain the
777:Alternatively, benzene may react with
426:359 °C (678 °F; 632 K)
178:
1320:, and Triphenylmethanesulfenamide, Ph
939:The use of tritylsodium as a strong,
903:Its sodium salt can be prepared from
308:Key: AAAQKTZKLRYKHR-UHFFFAOYSA-N
145:
968:Examples of triarylmethane dyes are
859:C-H bond is relatively weak, with a
1098:Triphenylmethyl hexafluorophosphate
1009:
318:Key: AAAQKTZKLRYKHR-UHFFFAOYAF
218:
24:
1123:"Triphenylmethane | 519-73-3"
1061:CSNO), tritylsulfenyl chloride (Ph
25:
1391:
1065:CSCl), and trityl sulfenamide (Ph
1285:-Glucose-1,2,3,4-Tetraacetate".
996:
976:
887:The trityl anion is isolable in
835:It can also be synthesized from
582:
515:
366:
42:
33:
1004:
578:(at 25 °C , 100 kPa).
1305:
1274:
1246:
1212:
1177:
1150:
1129:
1115:
682:
360:
13:
1:
1108:
1055:-nitrosotriphenylmethanethiol
339:c1c(cccc1)C(c2ccccc2)c3ccccc3
947:and related strong bases.
7:
1198:10.1021/acs.chemrev.6b00664
1137:"Ueber das Triphenylmethan"
1076:
10:
1396:
1269:, vol. 2, p. 607
961:
675:(trityl chloride) and the
80:,1″-Methylidynetrisbenzene
65:,1″-Methanetriyltribenzene
1350:10.1107/S0108270194004439
1037:COR + HBr → ROH + Ph
839:, which is prepared from
623:(sometimes also known as
572:
496:
491:
347:
327:
292:
85:
71:
55:
50:
41:
32:
1299:10.15227/orgsyn.022.0056
1171:10.15227/orgsyn.004.0081
1093:Triphenylmethyl chloride
861:bond dissociation energy
845:phosphorus pentachloride
783:triphenylmethyl chloride
673:triphenylmethyl chloride
1255:"Triphenylmethylsodium"
1139:(On triphenylmethane),
1103:Triphenylmethyl radical
736:Friedel–Crafts reaction
677:triphenylmethyl radical
477:Magnetic susceptibility
1370:Aromatic hydrocarbons
941:non-nucleophilic base
851:Reactions of C-H bond
952:acid–base titrations
837:benzylidene chloride
779:carbon tetrachloride
57:Preferred IUPAC name
1342:1994AcCrC..50.1362G
1240:10.1021/ja00710a077
958:Triarylmethane dyes
709:Quecksilberdiphenyl
659:, and some display
655:, many of them are
653:triarylmethane dyes
433:Solubility in water
384: g·mol
29:
1083:Tetraphenylmethane
1026:CCl + ROH → Ph
964:Triarylmethane dye
787:aluminium chloride
748:aluminium chloride
679:(trityl radical).
605:Infobox references
27:
1287:Organic Syntheses
1267:Collected Volumes
1260:Organic Syntheses
1192:(13): 8622–8648.
1159:Organic Syntheses
1088:Triphenylmethanol
970:bromocresol green
621:triphenyl methane
613:Chemical compound
611:
610:
561:Safety data sheet
540:Hazard statements
261:CompTox Dashboard
127:Interactive image
28:Triphenylmethane
16:(Redirected from
1387:
1375:Phenyl compounds
1354:
1353:
1336:(8): 1362–1366.
1309:
1303:
1302:
1278:
1272:
1270:
1263:
1250:
1244:
1243:
1216:
1210:
1209:
1186:Chemical Reviews
1181:
1175:
1174:
1154:
1148:
1147: : 906–908.
1133:
1127:
1126:
1119:
1033:deprotection: Ph
1016:protecting group
1010:Protecting group
1000:
980:
899:
617:Triphenylmethane
595:
589:
586:
585:
555:
551:
547:
519:
486:
405:
392:Colorless solid
383:
368:
362:
355:Chemical formula
285:
284:
269:
267:
251:
231:
220:
199:
191:
180:
169:
149:
129:
105:
79:
74:Triphenylmethane
64:
46:
37:
30:
26:
21:
1395:
1394:
1390:
1389:
1388:
1386:
1385:
1384:
1360:
1359:
1358:
1357:
1327:
1323:
1319:
1315:
1310:
1306:
1279:
1275:
1265:
1251:
1247:
1225:
1217:
1213:
1182:
1178:
1155:
1151:
1134:
1130:
1121:
1120:
1116:
1111:
1079:
1072:
1068:
1064:
1060:
1048:
1040:
1036:
1029:
1025:
1012:
1007:
990:malachite green
966:
960:
934:
930:
926:
923:CCl + 2 Na → (C
922:
918:
914:
882:diphenylmethane
871:
858:
853:
830:
826:
822:
816:
812:
808:
804:
800:
796:
772:
768:
764:
760:
729:Benzylenchlorid
726:
722:
718:
713:benzal chloride
706:
702:
698:
693:diphenylmercury
685:
670:
646:
642:
638:
614:
607:
602:
601:
600: ?)
591:
587:
583:
579:
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403:
381:
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365:
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119:
108:
95:
81:
77:
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67:
66:
62:
23:
22:
15:
12:
11:
5:
1393:
1383:
1382:
1377:
1372:
1356:
1355:
1325:
1321:
1317:
1313:
1304:
1273:
1245:
1223:
1211:
1176:
1149:
1128:
1113:
1112:
1110:
1107:
1106:
1105:
1100:
1095:
1090:
1085:
1078:
1075:
1070:
1066:
1062:
1058:
1047:
1044:
1043:
1042:
1038:
1034:
1031:
1027:
1023:
1018:for alcohols.
1011:
1008:
1006:
1003:
1002:
1001:
982:
981:
962:Main article:
959:
956:
937:
936:
932:
928:
924:
920:
916:
912:
901:
900:
869:
856:
852:
849:
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828:
824:
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724:
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700:
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684:
681:
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644:
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636:
612:
609:
608:
603:
581:
580:
576:standard state
573:
570:
569:
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53:
52:
48:
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39:
38:
9:
6:
4:
3:
2:
1392:
1381:
1378:
1376:
1373:
1371:
1368:
1367:
1365:
1351:
1347:
1343:
1339:
1335:
1331:
1308:
1300:
1296:
1292:
1288:
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1268:
1262:
1261:
1256:
1249:
1241:
1237:
1233:
1229:
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1215:
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1203:
1199:
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1191:
1187:
1180:
1172:
1168:
1164:
1160:
1153:
1146:
1142:
1138:
1132:
1124:
1118:
1114:
1104:
1101:
1099:
1096:
1094:
1091:
1089:
1086:
1084:
1081:
1080:
1074:
1056:
1054:
1032:
1021:
1020:
1019:
1017:
999:
995:
994:
993:
991:
987:
979:
975:
974:
973:
971:
965:
955:
953:
948:
946:
942:
910:
909:
908:
906:
898:
894:
893:
892:
890:
885:
883:
879:
874:
872:
868:
862:
848:
846:
842:
838:
818:
792:
791:
790:
788:
784:
780:
756:
755:
754:
752:
749:
745:
741:
737:
732:
730:
714:
710:
694:
690:
689:August Kekulé
680:
678:
674:
666:
662:
658:
657:pH indicators
654:
650:
634:
630:
626:
622:
618:
606:
599:
594:
577:
571:
568:
567:External MSDS
565:
562:
559:
558:
544:
541:
537:
536:
533:
530:
527:
523:
522:
518:
514:
511:
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500:
495:
490:
482:
478:
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473:
469:
463:
459:
456:
455:
451:
447:
445:
442:
441:
437:
434:
430:
429:
425:
423:
422:Boiling point
420:
419:
415:
413:
412:Melting point
410:
409:
401:
399:
396:
395:
391:
388:
387:
380:
378:
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374:
359:
356:
352:
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326:
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291:
283:
279:
278:DTXSID3060164
275:
274:
272:
262:
258:
257:
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245:
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241:
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237:
230:
226:
225:
223:
217:
213:
212:
205:
204:
202:
200:
195:
194:
190:
186:
183:
181:
179:ECHA InfoCard
176:
175:
168:
164:
163:
161:
159:
156:
155:
148:
144:
143:
141:
139:
136:
135:
128:
124:
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99:
97:
94:
90:
89:
84:
70:
58:
54:
49:
45:
40:
36:
31:
19:
1333:
1329:
1307:
1290:
1286:
1282:
1276:
1266:
1258:
1248:
1231:
1227:
1220:
1214:
1189:
1185:
1179:
1162:
1158:
1152:
1144:
1140:
1131:
1117:
1052:
1049:
1013:
1005:Trityl group
983:
967:
949:
945:butyllithium
938:
905:the chloride
902:
889:crown ethers
886:
875:
866:
854:
841:benzaldehyde
834:
776:
733:
728:
708:
686:
664:
661:fluorescence
624:
620:
616:
615:
531:
498:
461:
86:Identifiers
72:Other names
1234:(7): 2165.
1030:COR + HCl
878:delocalized
683:Preparation
629:hydrocarbon
526:Signal word
452:and hexane
448:Soluble in
389:Appearance
348:Properties
185:100.007.524
147:CHEBI:76212
1364:Categories
1109:References
935:CNa + NaCl
873:of 33.3.
827:+ HCl → Ph
773:CH + 3 HCl
744:chloroform
627:), is the
510:Pictograms
444:Solubility
438:Insoluble
377:Molar mass
249:8O4UTW9E17
158:ChemSpider
114:3D model (
93:CAS Number
988:-bearing
631:with the
501:labelling
483:−165.6×10
206:208-275-0
198:EC Number
1206:28281752
1077:See also
986:nitrogen
984:And the
823:CCl·AlCl
813:CCl·AlCl
751:catalyst
671:C, e.g.
492:Hazards
479:(χ)
103:519-73-3
1338:Bibcode
740:benzene
711:) with
651:called
633:formula
598:what is
596: (
532:Warning
487:cm/mol
458:Acidity
450:dioxane
398:Density
382:244.337
216:PubChem
1293:: 56.
1204:
1165:: 81.
855:The Ph
805:+ AlCl
765:+ CHCl
665:trityl
625:Tritan
593:verify
590:
563:(SDS)
485:
404:
332:SMILES
51:Names
18:Trityl
801:+ CCl
746:with
738:from
695:(Hg(C
470:33.3
406:g/cm
402:1.014
297:InChI
229:10614
167:10169
138:ChEBI
116:JSmol
1324:CSNH
1316:CONH
1202:PMID
1069:CSNH
843:and
809:→ Ph
769:→ Ph
742:and
723:CHCl
663:. A
649:dyes
554:H335
550:H319
546:H315
240:UNII
1346:doi
1328:".
1295:doi
1236:doi
1194:doi
1190:117
1167:doi
1073:).
1057:(Ph
1041:CBr
793:3 C
757:3 C
731:).
619:or
499:GHS
266:EPA
219:CID
76:1,1
61:1,1
1366::
1344:.
1334:50
1332:.
1291:22
1289:.
1264:;
1257:.
1232:92
1230:.
1200:.
1188:.
1161:.
1143:,
992::
972::
911:(C
907::
891::
847:.
831:CH
819:Ph
753::
727:,
715:(C
707:,
635:(C
552:,
548:,
503::
467:)
460:(p
370:16
364:19
1352:.
1348::
1340::
1326:2
1322:3
1318:2
1314:3
1301:.
1297::
1283:d
1271:.
1242:.
1238::
1224:a
1221:K
1208:.
1196::
1173:.
1169::
1163:4
1145:5
1125:.
1071:2
1067:3
1063:3
1059:3
1053:S
1039:3
1035:3
1028:3
1024:3
933:3
931:)
929:5
927:H
925:6
921:3
919:)
917:5
915:H
913:6
870:a
867:K
865:p
857:3
829:3
825:3
821:3
815:3
811:3
807:3
803:4
799:6
797:H
795:6
785:–
771:3
767:3
763:6
761:H
759:6
725:2
721:5
719:H
717:6
705:2
703:)
701:5
699:H
697:6
669:3
645:3
643:)
641:5
639:H
637:6
588:N
465:a
462:K
367:H
361:C
268:)
264:(
118:)
78:′
63:′
20:)
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