729:
743:
736:
224:
151:
395:
519:
24:
403:
375:
469:
871:
Tetraphenylphosphonium salts of inorganic or organometallic anions are often sought because they are easily crystallized. They also tend to be soluble in polar organic solvents such as
532:
988:
Schweizer, E. E.; Baldacchini, C. J.; Rheingold, A. L. (1989). "Tetraphenylphosphonium
Chloride Monohydrate, Tetraphenylphosphonium Bromide and Tetraphenylphosphonium Iodide".
819:
The compound was originally prepared as the corresponding bromide salt (CAS No. 2751-90-8), which in turn was synthesized by passing dry oxygen through the reaction of
1194:
Bray, J.; Locke, J.; McCleverty, J. A.; Coucouvanis, D. (1972). "Bis[cis -1,2-dicyanoethene-1,2-dithiolato(1- or 2-)] Complexes of Cobalt and Iron".
280:
88:
1242:
465:
1145:
Hadjikyriacou, A. I.; Coucouvanis, D. (1990). "Tetraphenylphosphonium Salts of [Mo2 (S) N (S2 )6-N ]2- Thioanions and
Derivatives".
1252:
1058:
Marcoux, David; Charette, André B. (2008). "Nickel-Catalyzed
Synthesis of Phosphonium Salts from Aryl Halides and Triphenylphosphine".
1215:
1178:
1129:
238:
1085:
Dodonow, J.; Medox, H. (1928). "Zur
Kenntnis der Grignardschen Reaktion: Über die Darstellung von Tetraphenyl-phosphoniumsalzen".
713:
salts are of interest as they often crystallise easily. The rigidity of the phenyl groups facilitates packing and elevates the
676:
721:. Also, since these salts are soluble in organic media, a wide range of solvents can be employed for their crystallisation.
457:
539:
728:
439:
742:
257:
InChI=1S/C24H20P.ClH/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;/h1-20H;1H/q+1;/p-1
247:
InChI=1S/C24H20P.ClH/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;/h1-20H;1H/q+1;/p-1
202:
493:
394:
1112:
Dilworth, J. R.; Hussain, W.; Hutson, A. J.; Jones, C. J.; McQuillan, F. S. (1996). "Tetrahalo
Oxorhenate Anions".
735:
1247:
158:
832:
718:
928:
485:
481:
820:
623:
473:
146:
900:
108:
698:
417:
387:
953:
1032:
997:
962:
769:
599:
36:
219:
756:
54:
1237:
824:
798:
445:
1023:
Blake, A. J.; Garner, C. D.; Tunney, J. M. (2003). "Tetraphenylphosphonium
Chloride Dihydrate".
598:. Tetraphenylphosphonium and especially tetraphenylarsonium salts were formerly of interest in
453:
1211:
1174:
1125:
876:
762:
1203:
1166:
1117:
1094:
1067:
1040:
1005:
970:
828:
607:
303:
128:
477:
627:
461:
64:
223:
150:
1036:
1001:
966:
510:
1231:
896:
794:
714:
360:
139:
501:
872:
449:
190:
691:
603:
431:
1207:
1121:
489:
1170:
1044:
1009:
974:
880:
329:
119:
1200:-1,2-Dicyanoethene-1,2-dithiolato(1- or 2-)] Complexes of Cobalt and Iron
1098:
427:
687:
1071:
658:
647:
610:
is used to generate lipophilic salts from inorganic and organometallic
350:
177:
159:
423:
661:
595:
99:
509:
Except where otherwise noted, data are given for materials in their
611:
87:
77:
23:
793:
and many analogous compounds can be prepared by the reaction of
497:
207:
365:
272 to 274 °C (522 to 525 °F; 545 to 547 K)
827:. The synthesis probably proceeds via the reaction of the
626:, again because it allows inorganic anions to dissolve in
1202:. Inorganic Syntheses. Vol. XIII. pp. 187–195.
690:
salt, which is the normal item of commerce, as well as a
527:
1165:. Inorganic Syntheses. pp. 39–47volume=XXVII.
189:
63:
1087:Berichte der Deutschen Chemischen Gesellschaft
879:. Examples include the tetraphenylphosphonium
8:
554:is the chemical compound with the formula
222:
149:
127:
15:
906:
890:
886:
858:
854:
845:
841:
811:
807:
788:
723:
670:
652:
646:. It consists of tetraphenylphosphonium
641:
617:
589:
581:
573:
565:
561:
557:
319:
315:
311:
1147:Tetraphenylphosphonium Salts of [Mo
920:
606:and related oxyanions. This colourless
288:.c1c(cccc1)(c2ccccc2)(c3ccccc3)c4ccccc4
285:
243:
218:
140:
267:Key: WAGFXJQAIZNSEQ-UHFFFAOYSA-M
250:Key: WAGFXJQAIZNSEQ-UHFFFAOYSA-M
107:
7:
1116:. Vol. XXXI. pp. 257–262.
260:Key: WAGFXJQAIZNSEQ-REWHXWOFAO
180:
14:
929:"Tetraphenylphosphonium chloride"
1243:Quaternary phosphonium compounds
741:
734:
727:
517:
393:
22:
17:Tetraphenylphosphonium chloride
552:Tetraphenylphosphonium chloride
513:(at 25 °C , 100 kPa).
41:Tetraphenylphosphanium chloride
638:The structure of this salt is
634:Structure and basic properties
1:
751:constituent ions in the solid
1163:] Thioanions and Derivatives
903:are also isolated as their
801:catalysed by nickel salts:
1269:
1253:Organophosphorus compounds
1208:10.1002/9780470132449.ch39
1122:10.1002/9780470132623.ch42
1171:10.1002/9780470132586.ch8
1045:10.1107/S1600536802021682
1010:10.1107/S0108270189000363
975:10.1107/S0108270186092612
719:quaternary ammonium salts
507:
374:
369:
296:
276:
234:
47:
35:
30:
21:
1099:10.1002/cber.19280610505
933:pubchem.ncbi.nlm.nih.gov
833:triphenylphosphine oxide
774:of the crystal structure
717:relative to alkyl-based
440:Precautionary statements
857:P]OMgBr + HBr → [Ph
821:phenylmagnesium bromide
686:Cl crystallises as the
624:phase-transfer catalyst
1072:10.1002/adsc.200800542
1025:Acta Crystallographica
990:Acta Crystallographica
955:Acta Crystallographica
901:maleonitriledithiolate
594:, where Ph stands for
699:X-ray crystallography
770:ball-and-stick model
600:gravimetric analysis
37:Preferred IUPAC name
1114:Inorganic Syntheses
1037:2003AcCrE..59O...9B
1002:1989AcCrC..45.1236S
967:1986AcCrC..42.1271R
757:space-filling model
337: g·mol
18:
825:triphenylphosphine
799:triphenylphosphine
540:Infobox references
16:
1066:(18): 2967–2974.
1060:Adv. Synth. Catal
877:dimethylformamide
861:P]Br + "Mg(OH)Br"
779:
778:
775:
765:
763:crystal structure
752:
694:and a dihydrate.
548:Chemical compound
546:
545:
418:Hazard statements
345:colourless solid
203:CompTox Dashboard
89:Interactive image
1260:
1248:Phenyl compounds
1222:
1221:
1191:
1185:
1184:
1142:
1136:
1135:
1109:
1103:
1102:
1082:
1076:
1075:
1055:
1049:
1048:
1020:
1014:
1013:
996:(8): 1236–1239.
985:
979:
978:
961:(9): 1271–1272.
950:
944:
943:
941:
939:
925:
910:
894:
867:Use in synthesis
862:
849:
829:Grignard reagent
815:
792:
768:
755:
750:
745:
738:
731:
724:
712:
711:
710:
707:
674:
666:
656:
645:
628:organic solvents
621:
593:
585:
577:
569:
530:
524:
521:
520:
503:
499:
495:
491:
487:
483:
479:
475:
471:
467:
463:
459:
455:
451:
447:
433:
429:
425:
397:
336:
323:
304:Chemical formula
227:
226:
211:
209:
193:
182:
161:
153:
142:
131:
111:
91:
67:
26:
19:
1268:
1267:
1263:
1262:
1261:
1259:
1258:
1257:
1228:
1227:
1226:
1225:
1218:
1193:
1192:
1188:
1181:
1162:
1158:
1154:
1150:
1144:
1143:
1139:
1132:
1111:
1110:
1106:
1084:
1083:
1079:
1057:
1056:
1052:
1022:
1021:
1017:
987:
986:
982:
952:
951:
947:
937:
935:
927:
926:
922:
917:
908:
904:
899:. Complexes of
892:
888:
884:
869:
860:
856:
852:
847:
843:
839:
813:
809:
805:
790:
786:
784:
773:
760:
708:
705:
704:
702:
685:
672:
668:
664:
654:
650:
643:
639:
636:
622:is useful as a
619:
615:
591:
587:
583:
579:
575:
571:
567:
563:
559:
555:
549:
542:
537:
536:
535: ?)
526:
522:
518:
514:
442:
420:
406:
390:
334:
321:
317:
313:
309:
306:
292:
289:
284:
283:
272:
269:
268:
262:
261:
258:
252:
251:
248:
242:
241:
230:
212:
205:
196:
183:
171:
134:
114:
94:
81:
70:
57:
43:
42:
12:
11:
5:
1266:
1264:
1256:
1255:
1250:
1245:
1240:
1230:
1229:
1224:
1223:
1216:
1186:
1179:
1160:
1156:
1152:
1148:
1137:
1130:
1104:
1093:(5): 907–911.
1077:
1050:
1015:
980:
945:
919:
918:
916:
913:
897:thiomolybdates
895:) and various
868:
865:
864:
863:
850:
817:
816:
783:
780:
777:
776:
766:
753:
747:
746:
739:
732:
683:
635:
632:
570:, abbreviated
547:
544:
543:
538:
516:
515:
511:standard state
508:
505:
504:
470:P305+P351+P338
443:
438:
435:
434:
421:
416:
413:
412:
407:
402:
399:
398:
391:
386:
383:
382:
372:
371:
367:
366:
363:
357:
356:
353:
347:
346:
343:
339:
338:
332:
326:
325:
307:
302:
299:
298:
294:
293:
291:
290:
287:
279:
278:
277:
274:
273:
271:
270:
266:
265:
263:
259:
256:
255:
253:
249:
246:
245:
237:
236:
235:
232:
231:
229:
228:
220:DTXSID00897533
215:
213:
201:
198:
197:
195:
194:
186:
184:
176:
173:
172:
170:
169:
165:
163:
155:
154:
144:
136:
135:
133:
132:
124:
122:
116:
115:
113:
112:
104:
102:
96:
95:
93:
92:
84:
82:
75:
72:
71:
69:
68:
60:
58:
53:
50:
49:
45:
44:
40:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1265:
1254:
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1235:
1233:
1219:
1217:9780470132449
1213:
1209:
1205:
1201:
1197:
1190:
1187:
1182:
1180:9780470132586
1176:
1172:
1168:
1164:
1141:
1138:
1133:
1131:9780470132623
1127:
1123:
1119:
1115:
1108:
1105:
1100:
1096:
1092:
1088:
1081:
1078:
1073:
1069:
1065:
1061:
1054:
1051:
1046:
1042:
1038:
1034:
1031:(1): o9–o10.
1030:
1026:
1019:
1016:
1011:
1007:
1003:
999:
995:
991:
984:
981:
976:
972:
968:
964:
960:
956:
949:
946:
934:
930:
924:
921:
914:
912:
902:
898:
882:
878:
874:
866:
851:
838:
837:
836:
834:
830:
826:
822:
804:
803:
802:
800:
796:
795:chlorobenzene
781:
771:
767:
764:
758:
754:
749:
748:
744:
740:
737:
733:
730:
726:
725:
722:
720:
716:
715:melting point
700:
695:
693:
689:
680:
678:
663:
660:
649:
633:
631:
629:
625:
613:
609:
605:
601:
597:
553:
541:
534:
529:
512:
506:
444:
441:
437:
436:
422:
419:
415:
414:
411:
408:
405:
401:
400:
396:
392:
389:
385:
384:
380:
378:
373:
368:
364:
362:
361:Melting point
359:
358:
354:
352:
349:
348:
344:
341:
340:
333:
331:
328:
327:
308:
305:
301:
300:
295:
286:
282:
275:
264:
254:
244:
240:
233:
225:
221:
217:
216:
214:
204:
200:
199:
192:
188:
187:
185:
179:
175:
174:
167:
166:
164:
162:
157:
156:
152:
148:
145:
143:
141:ECHA InfoCard
138:
137:
130:
126:
125:
123:
121:
118:
117:
110:
106:
105:
103:
101:
98:
97:
90:
86:
85:
83:
79:
74:
73:
66:
62:
61:
59:
56:
52:
51:
46:
38:
34:
29:
25:
20:
1199:
1195:
1189:
1146:
1140:
1113:
1107:
1090:
1086:
1080:
1063:
1059:
1053:
1028:
1024:
1018:
993:
989:
983:
958:
954:
948:
936:. Retrieved
932:
923:
873:acetonitrile
870:
844:PO → [Ph
818:
785:
696:
681:
637:
551:
550:
409:
376:
109:ChEMBL223885
48:Identifiers
938:12 December
840:PhMgBr + Ph
782:Preparation
692:monohydrate
677:tetrahedral
604:perchlorate
404:Signal word
342:Appearance
297:Properties
147:100.016.265
1232:Categories
915:References
881:perrhenate
806:PhCl + PPh
675:cation is
388:Pictograms
355:1.27 g dm
330:Molar mass
120:ChemSpider
76:3D model (
55:CAS Number
1238:Chlorides
889:][ReO
810:→ [Ph
688:anhydrous
494:P403+P233
486:P337+P313
482:P332+P313
466:P304+P340
462:P302+P352
379:labelling
168:217-890-3
160:EC Number
65:2001-45-8
1196:Bis[
905:[PPh
885:[PPh
787:[PPh
669:[PPh
659:chloride
651:[PPh
640:[PPh
614:. Thus,
588:[PPh
370:Hazards
310:[P(C
1033:Bibcode
998:Bibcode
963:Bibcode
911:salts.
853:[Ph
848:P]OMgBr
772:of part
761:of the
759:of part
648:cations
616:[Ph
556:[(C
533:what is
531: (
410:Warning
351:Density
324:
178:PubChem
1214:
1177:
1128:
667:. The
662:anions
612:anions
596:phenyl
528:verify
525:
335:374.85
281:SMILES
191:164911
129:144578
100:ChEMBL
31:Names
831:with
797:with
239:InChI
78:JSmol
1212:ISBN
1175:ISBN
1126:ISBN
940:2021
875:and
823:and
814:P]Cl
657:and
608:salt
568:P]Cl
502:P501
498:P405
490:P362
478:P321
474:P312
458:P280
454:P271
450:P264
446:P261
432:H335
428:H319
424:H315
1204:doi
1198:cis
1167:doi
1161:6-n
1151:(S)
1118:doi
1095:doi
1068:doi
1064:350
1041:doi
1029:E59
1006:doi
994:C45
971:doi
959:C42
791:]Cl
703:PPh
697:In
682:PPh
644:]Cl
602:of
592:]Cl
586:or
580:PPh
578:or
576:PCl
377:GHS
322:]Cl
208:EPA
181:CID
1234::
1210:.
1173:.
1155:(S
1124:.
1091:61
1089:.
1062:.
1039:.
1027:.
1004:.
992:.
969:.
957:.
931:.
835:.
701:,
679:.
665:Cl
630:.
620:P]
584:Cl
572:Ph
500:,
496:,
492:,
488:,
484:,
480:,
476:,
472:,
468:,
464:,
460:,
456:,
452:,
448:,
430:,
426:,
381::
1220:.
1206::
1183:.
1169::
1159:)
1157:2
1153:n
1149:2
1134:.
1120::
1101:.
1097::
1074:.
1070::
1047:.
1043::
1035::
1012:.
1008::
1000::
977:.
973::
965::
942:.
909:]
907:4
893:]
891:4
887:4
883:(
859:4
855:4
846:4
842:3
812:4
808:3
789:4
709:4
706:+
684:4
673:]
671:4
655:]
653:4
642:4
618:4
590:4
582:4
574:4
566:4
564:)
562:5
560:H
558:6
523:N
320:4
318:)
316:5
314:H
312:6
210:)
206:(
80:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
