294:
201:
531:
521:
526:
52:
28:
802:, which is far less expensive but less easily handled. A slightly thermally more stable compound is morpho-DAST. Acid-labile substrates are less likely to undergo rearrangement and elimination since DAST is less prone to contamination with acids. Reaction temperatures are milder as well – alcohols typically react at −78 °C and ketones around 0 °C.
719:
37:
539:
501:
862:
that can be used with no decrease in yield. Because of the dangers involved in the preparation of DAST (glass etching, possibility of exothermic events), it is often purchased from a commercial source. At one time
1109:
Gauri S. Lal; Guido P. Pez; Reno J. Pesaresi; Frank M. Prozonic (1999). "Bis(2-methoxyethyl)aminosulfur trifluoride: a new broad-spectrum deoxofluorinating agent with enhanced thermal stability".
661:
899:(trade name: XtalFluor-M) are reagents related to DAST with less explosive potential. XtalFluor-E has been jointly developed by OmegaChem Inc. and Manchester Organics Ltd. in 2009–2010.
649:
150:
798:, effects the same transformation but will also convert the acyl fluoride to the trifluoromethyl derivative. For laboratory-scale operations, DAST is used in preference to SF
732:
790:
to the corresponding alkyl fluorides as well as aldehydes and unhindered ketones to geminal difluorides. Carboxylic acids react no further than the acyl fluoride.
343:
1039:
L. N. Markovskij; V. E. Pashinnik; A. V. Kirsanov (1973). "Application of
Dialkylaminosulfur Trifluorides in the Synthesis of Fluoroorganic Compounds".
657:
1135:
l'Heureux, A.; Beaulieu, F.; Bennett, C.; Bill, D. R.; Clayton, S.; Laflamme, F. O.; Mirmehrabi, M.; Tadayon, S.; Tovell, D.; Couturier, M. (2010).
1247:
1267:
589:
867:
was one of the few suppliers of the chemical but a number of companies now sell DAST. Carbolabs was acquired by Sigma-Aldrich in 1998.
1066:
REACTION OF SULFOXIDES WITH DIETHYLAMINOSULFUR TRIFLUORIDE: FLUOROMETHYL PHENYL SULFONE, A REAGENT FOR THE SYNTHESIS OF FLUOROALKENES
953:
913:
308:
1262:
1257:
637:
653:
482:
633:
1252:
583:
251:
1137:"Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling†,‡"
272:
530:
739:
208:
1242:
1082:
Messina, P. A.; Mange, K. C.; Middleton, W. J. (1989). "Aminosulfur
Trifluorides: Relative Thermal Stability".
775:
601:
143:
520:
669:
641:
525:
196:
847:
609:
759:
553:
513:
1187:
Beaulieu, F.; Beauregard, L. P.; Courchesne, G.; Couturier, M.; Laflamme, F. O.; l’Heureux, A. (2009).
895:-(2-methoxyethyl)aminosulfur trifluoride (trade name: Deoxo-Fluor) and difluoro(morpholino)sulfonium
1189:"Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents"
888:
811:
791:
665:
64:
1065:
289:
625:
109:
597:
693:
617:
613:
1004:
Middleton, William J. (1975-03-01). "New fluorinating reagents. Dialkylaminosulfur fluorides".
629:
1218:
1166:
1021:
949:
936:
Fauq, Abdul H.; Singh, Rajendra P.; Meshri, Dayal T. (2006). "Diethylaminosulfurtrifluoride".
896:
1208:
1200:
1156:
1148:
1114:
1091:
1048:
1013:
969:
Markovskii, LN; Pashinnik, VE; KIRSANOVA, NA (1975). "Sulfur Bis(dialkylamino
Difluorides".
941:
908:
689:
447:
371:
178:
673:
260:
119:
859:
677:
645:
685:
293:
200:
1213:
1188:
1161:
1136:
710:
571:
1095:
1236:
855:
436:
189:
701:
621:
469:
240:
945:
593:
458:
405:
169:
1025:
992:
864:
605:
567:
1222:
1170:
559:
51:
27:
1052:
787:
1017:
317:
InChI=1S/3C4H12NS.3FH/c3*1-3-6(5)4-2;;;/h3*3-5H2,1-2H3;3*1H/q3*+1;;;/p-3
771:
464:
426:
327:
InChI=1/3C4H12NS.3FH/c3*1-3-6(5)4-2;;;/h3*3-5H2,1-2H3;3*1H/q3*+1;;;/p-3
227:
209:
1204:
1152:
1118:
778:. The compound is colourless; older samples assume an orange colour.
810:
DAST is prepared by the reaction of diethylaminotrimethylsilane and
709:
Except where otherwise noted, data are given for materials in their
563:
891:. To minimize accidents, samples are maintained below 50 °C.
575:
149:
142:
132:
441:
30 to 32 °C (86 to 90 °F; 303 to 305 K) at 3 mmHg
987:
W. J. Middleton, E. M. Bingham "Diethylaminosulfur
Trifluoride"
697:
36:
681:
277:
35:
26:
1130:
1128:
875:
Upon heating, DAST converts to the highly explosive (NEt
727:
1182:
1180:
1072:, Coll. Vol. 9, p.446 (1998); Vol. 72, p.209 (1995)
239:
118:
938:Encyclopedia of Reagents for Organic Synthesis
8:
292:
199:
177:
15:
1212:
1160:
259:
925:
496:corrosive, flammable, can be explosive
348:
313:
288:
931:
929:
190:
320:Key: OJRFYRBETDFODT-UHFFFAOYSA-K
7:
977:: 74–77 – via Web of Science.
330:Key: OJRFYRBETDFODT-DFZHHIFOAR
230:
14:
914:Fluorination with aminosulfuranes
1141:The Journal of Organic Chemistry
1006:The Journal of Organic Chemistry
770:. This liquid is a fluorinating
717:
529:
524:
519:
395:
389:
383:
50:
871:Safety and alternative reagents
713:(at 25 °C , 100 kPa).
17:Diethylaminosulfur trifluoride
1248:Reagents for organic chemistry
991:Vol. 6, p.440; Vol. 57, p.50.
752:Diethylaminosulfur trifluoride
483:Occupational safety and health
398:
377:
97:diethyl(trifluorosulfido)amine
1:
1096:10.1016/S0022-1139(00)83974-3
1084:Journal of Fluorine Chemistry
946:10.1002/047084289X.rd175.pub2
846:The original paper calls for
971:Zhurnal Organicheskoi Khimii
22:
1284:
774:used for the synthesis of
356:...N(CC)CC.CC(N)CC.CC(N)CC
1268:Sulfur–nitrogen compounds
707:
500:
480:
475:
364:
339:
304:
102:
94:
63:
58:
49:
21:
989:Organic Syntheses, Coll.
782:Use in organic synthesis
776:organofluorine compounds
584:Precautionary statements
88:-trifluoro-λ-sulfanamine
1111:Chemical Communications
1263:Organosulfur compounds
1258:Diethylamino compounds
848:trichlorofluoromethane
40:
31:
760:organosulfur compound
39:
30:
1053:10.1055/s-1973-22302
889:sulfur tetrafluoride
812:sulfur tetrafluoride
792:Sulfur tetrafluoride
65:Preferred IUPAC name
1253:Fluorinating agents
1018:10.1021/jo00893a007
762:with the formula Et
448:Solubility in water
413: g·mol
18:
887:with expulsion of
740:Infobox references
453:Reacts with water
41:
32:
16:
1205:10.1021/ol902039q
1199:(21): 5050–5053.
1153:10.1021/jo100504x
1147:(10): 3401–3411.
1070:Organic Syntheses
897:tetrafluoroborate
860:green alternative
748:Chemical compound
746:
745:
554:Hazard statements
273:CompTox Dashboard
151:Interactive image
144:Interactive image
45:
44:
1275:
1227:
1226:
1216:
1184:
1175:
1174:
1164:
1132:
1123:
1122:
1119:10.1039/a808517j
1106:
1100:
1099:
1079:
1073:
1063:
1057:
1056:
1036:
1030:
1029:
1001:
995:
985:
979:
978:
966:
960:
959:
933:
909:Ishikawa reagent
854:) as a solvent.
730:
724:
721:
720:
703:
699:
695:
691:
687:
683:
679:
675:
671:
667:
663:
659:
655:
651:
647:
643:
639:
635:
631:
627:
623:
619:
615:
611:
607:
603:
599:
595:
591:
577:
573:
569:
565:
561:
533:
528:
523:
412:
400:
397:
391:
385:
379:
372:Chemical formula
297:
296:
281:
279:
263:
243:
232:
211:
203:
192:
181:
153:
146:
122:
54:
23:
19:
1283:
1282:
1278:
1277:
1276:
1274:
1273:
1272:
1243:Organofluorides
1233:
1232:
1231:
1230:
1193:Organic Letters
1186:
1185:
1178:
1134:
1133:
1126:
1108:
1107:
1103:
1081:
1080:
1076:
1064:
1060:
1047:(12): 787–789.
1038:
1037:
1033:
1003:
1002:
998:
986:
982:
968:
967:
963:
956:
935:
934:
927:
922:
905:
886:
882:
878:
873:
841:
837:
833:
829:
825:
821:
808:
801:
797:
784:
769:
765:
749:
742:
737:
736:
735: ?)
726:
722:
718:
714:
586:
556:
542:
516:
493:
467:
450:
421:colourless oil
410:
394:
388:
382:
374:
360:
357:
352:
351:FS(F)(F)N(CC)CC
347:
346:
335:
332:
331:
328:
322:
321:
318:
312:
311:
300:
282:
275:
266:
246:
233:
221:
184:
156:
136:
125:
112:
98:
90:
89:
12:
11:
5:
1281:
1279:
1271:
1270:
1265:
1260:
1255:
1250:
1245:
1235:
1234:
1229:
1228:
1176:
1124:
1113:(2): 215–216.
1101:
1090:(1): 137–143.
1074:
1058:
1031:
1012:(5): 574–578.
996:
993:Online version
980:
961:
954:
924:
923:
921:
918:
917:
916:
911:
904:
901:
884:
880:
876:
872:
869:
844:
843:
839:
835:
831:
827:
823:
819:
807:
804:
799:
795:
786:DAST converts
783:
780:
767:
763:
747:
744:
743:
738:
716:
715:
711:standard state
708:
705:
704:
662:P305+P351+P338
650:P303+P361+P353
642:P301+P330+P331
587:
582:
579:
578:
557:
552:
549:
548:
543:
538:
535:
534:
517:
512:
509:
508:
498:
497:
494:
491:
488:
487:
478:
477:
473:
472:
461:
455:
454:
451:
446:
443:
442:
439:
433:
432:
429:
423:
422:
419:
415:
414:
408:
402:
401:
392:
386:
380:
375:
370:
367:
366:
362:
361:
359:
358:
355:
353:
350:
342:
341:
340:
337:
336:
334:
333:
329:
326:
325:
323:
319:
316:
315:
307:
306:
305:
302:
301:
299:
298:
290:DTXSID20191484
285:
283:
271:
268:
267:
265:
264:
256:
254:
248:
247:
245:
244:
236:
234:
226:
223:
222:
220:
219:
215:
213:
205:
204:
194:
186:
185:
183:
182:
174:
172:
166:
165:
162:
161:Abbreviations
158:
157:
155:
154:
147:
139:
137:
130:
127:
126:
124:
123:
115:
113:
108:
105:
104:
100:
99:
96:
92:
91:
68:
67:
61:
60:
56:
55:
47:
46:
43:
42:
33:
13:
10:
9:
6:
4:
3:
2:
1280:
1269:
1266:
1264:
1261:
1259:
1256:
1254:
1251:
1249:
1246:
1244:
1241:
1240:
1238:
1224:
1220:
1215:
1210:
1206:
1202:
1198:
1194:
1190:
1183:
1181:
1177:
1172:
1168:
1163:
1158:
1154:
1150:
1146:
1142:
1138:
1131:
1129:
1125:
1120:
1116:
1112:
1105:
1102:
1097:
1093:
1089:
1085:
1078:
1075:
1071:
1067:
1062:
1059:
1054:
1050:
1046:
1042:
1035:
1032:
1027:
1023:
1019:
1015:
1011:
1007:
1000:
997:
994:
990:
984:
981:
976:
972:
965:
962:
957:
955:0-471-93623-5
951:
947:
943:
939:
932:
930:
926:
919:
915:
912:
910:
907:
906:
902:
900:
898:
894:
890:
870:
868:
866:
861:
857:
856:Diethyl ether
853:
849:
817:
816:
815:
813:
805:
803:
793:
789:
781:
779:
777:
773:
761:
757:
753:
741:
734:
729:
712:
706:
588:
585:
581:
580:
558:
555:
551:
550:
547:
544:
541:
537:
536:
532:
527:
522:
518:
515:
511:
510:
506:
504:
499:
495:
490:
489:
485:
484:
479:
474:
471:
466:
462:
460:
457:
456:
452:
449:
445:
444:
440:
438:
437:Boiling point
435:
434:
430:
428:
425:
424:
420:
417:
416:
409:
407:
404:
403:
376:
373:
369:
368:
363:
354:
349:
345:
338:
324:
314:
310:
303:
295:
291:
287:
286:
284:
274:
270:
269:
262:
258:
257:
255:
253:
250:
249:
242:
238:
237:
235:
229:
225:
224:
217:
216:
214:
212:
207:
206:
202:
198:
195:
193:
191:ECHA InfoCard
188:
187:
180:
176:
175:
173:
171:
168:
167:
163:
160:
159:
152:
148:
145:
141:
140:
138:
134:
129:
128:
121:
117:
116:
114:
111:
107:
106:
101:
93:
87:
83:
79:
75:
71:
66:
62:
57:
53:
48:
38:
34:
29:
25:
24:
20:
1196:
1192:
1144:
1140:
1110:
1104:
1087:
1083:
1077:
1069:
1061:
1044:
1040:
1034:
1009:
1005:
999:
988:
983:
974:
970:
964:
937:
892:
874:
851:
845:
809:
785:
755:
751:
750:
545:
502:
492:Main hazards
481:
470:acetonitrile
463:reacts with
103:Identifiers
95:Other names
85:
81:
77:
73:
69:
540:Signal word
486:(OHS/OSH):
468:soluble in
431:1.220 g/cm
418:Appearance
365:Properties
197:100.048.866
1237:Categories
920:References
514:Pictograms
459:Solubility
406:Molar mass
261:78622BV6IJ
170:ChemSpider
131:3D model (
120:38078-09-0
110:CAS Number
1041:Synthesis
1026:0022-3263
865:Carbolabs
806:Synthesis
758:) is the
694:P403+P235
690:P370+P378
658:P304+P340
654:P304+P312
646:P302+P352
638:P301+P312
505:labelling
218:253-771-2
210:EC Number
76:-Diethyl-
1223:19799406
1171:20405933
903:See also
852:Freon-11
788:alcohols
476:Hazards
1214:2770860
1162:2869536
772:reagent
733:what is
731: (
465:ethanol
427:Density
228:PubChem
1221:
1211:
1169:
1159:
1024:
952:
728:verify
725:
546:Danger
411:161.19
344:SMILES
241:123472
179:110068
59:Names
858:is a
838:+ Me
822:NSiMe
309:InChI
164:DAST
133:JSmol
1219:PMID
1167:PMID
1045:1973
1022:ISSN
950:ISBN
830:→ Et
826:+ SF
794:, SF
756:DAST
702:P501
698:P405
686:P363
682:P330
678:P322
674:P321
670:P312
666:P310
634:P280
630:P271
626:P270
622:P264
618:P261
614:P260
610:P243
606:P242
602:P241
598:P240
594:P233
590:P210
576:H332
572:H314
568:H312
564:H302
560:H226
252:UNII
1209:PMC
1201:doi
1157:PMC
1149:doi
1115:doi
1092:doi
1049:doi
1014:doi
942:doi
893:Bis
842:SiF
834:NSF
766:NSF
503:GHS
278:EPA
231:CID
1239::
1217:.
1207:.
1197:11
1195:.
1191:.
1179:^
1165:.
1155:.
1145:75
1143:.
1139:.
1127:^
1088:42
1086:.
1068:,
1043:.
1020:.
1010:40
1008:.
975:11
973:.
948:.
940:.
928:^
883:SF
818:Et
814::
700:,
696:,
692:,
688:,
684:,
680:,
676:,
672:,
668:,
664:,
660:,
656:,
652:,
648:,
644:,
640:,
636:,
632:,
628:,
624:,
620:,
616:,
612:,
608:,
604:,
600:,
596:,
592:,
574:,
570:,
566:,
562:,
507::
387:10
1225:.
1203::
1173:.
1151::
1121:.
1117::
1098:.
1094::
1055:.
1051::
1028:.
1016::
958:.
944::
885:2
881:2
879:)
877:2
850:(
840:3
836:3
832:2
828:4
824:3
820:2
800:4
796:4
768:3
764:2
754:(
723:N
399:S
396:N
393:3
390:F
384:H
381:4
378:C
280:)
276:(
135:)
86:S
84:,
82:S
80:,
78:S
74:N
72:,
70:N
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
