616:
197:
122:
35:
393:
394:
389:
473:
392:
647:
results in the formation of acyloxyborohydride species other than sodium triacetoxyborohydride. These modified species can perform a variety of reductions not normally associated with borohydride chemistry, such as alcohols to hydrocarbons and nitriles to primary amines.
702:
Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. (1996). "Reductive
Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures1".
410:
417:
486:
615:
853:
395:
236:
99:
741:
Abdel-Magid, A. F.; Mehrman, S. J. (2006). "A Review on the Use of Sodium
Triacetoxyborohydride in the Reductive Amination of Ketones and Aldehydes".
685:
Gordon W. Gribble, Ahmed F. Abdel-Magid, "Sodium
Triacetoxyborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007, John Wiley & Sons.
211:
34:
358:
493:
154:
175:
403:
872:
882:
657:
602:
591:
455:
117:
818:
Gribble, Gordon, W. (1998). "Sodium borohydride in carboxylic acid media: a phenomenal reduction system".
877:
847:
340:
803:
595:
192:
65:
801:
Pandit, C. R.; Mani, N. S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts".
835:
663:
587:
352:
627:
may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts.
887:
720:
541:
517:
429:
827:
781:
750:
712:
686:
323:
259:
163:
75:
644:
196:
121:
537:
464:
866:
312:
143:
110:
17:
839:
435:
545:
690:
609:. It reacts only slowly with ethanol and isopropanol and can be used with these.
549:
533:
281:
786:
769:
768:
Magano, Javier; Kiser, E. Jason; Shine, Russell J.; Chen, Michael H. (2013).
724:
594:. It reduces aldehydes but not most ketones. It is especially suitable for
605:, the triacetoxyborohydride hydrolyzes readily, nor is it compatible with
606:
416:
409:
402:
375:
302:
130:
754:
716:
317:
116 to 120 °C (241 to 248 °F; 389 to 393 K) decomposes
831:
463:
Except where otherwise noted, data are given for materials in their
770:"Oxindole Synthesis via Palladium-catalyzed C-H Functionalization"
362:
220:
InChI=1S/C6H9BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h1-3H3;/q-1;+1
98:
88:
660:- a slightly stronger reductant, but amenable to protic solvents
449:
586:
Sodium triacetoxyborohydride is a milder reducing agent than
614:
180:
387:
481:
142:
391:
74:
8:
852:: CS1 maint: multiple names: authors list (
53:; STAB; STABH; Sodium triacetoxyhydroborate
743:Organic Process Research & Development
195:
120:
26:
785:
162:
638:
574:
570:
566:
562:
558:
527:
523:
271:
267:
678:
241:
216:
191:
845:
736:
734:
544:. This colourless salt is prepared by
111:
223:Key: AGGHKNBCHLWKHY-UHFFFAOYSA-N
7:
133:
25:
705:The Journal of Organic Chemistry
582:Comparison with related reagents
471:
33:
666:- a stronger, cheaper reductant
467:(at 25 °C , 100 kPa).
1:
691:10.1002/047084289X.rs112.pub2
619:Reductive amination with STAB
28:Sodium triacetoxyborohydride
510:sodium triacetoxyhydroborate
506:Sodium triacetoxyborohydride
548:of sodium borohydride with
904:
598:of aldehydes and ketones.
244:(OC(=O)C)(OC(=O)C)OC(=O)C.
461:
441:
369:
333:
252:
232:
207:
58:
46:
41:
32:
820:Chemical Society Reviews
787:10.15227/orgsyn.090.0074
658:Sodium cyanoborohydride
603:sodium cyanoborohydride
592:sodium cyanoborohydride
512:, commonly abbreviated
456:Sodium cyanoborohydride
631:Monoacetoxyborohydride
620:
398:
618:
397:
341:Coordination geometry
18:Triacetoxyborohydride
596:reductive aminations
380:(fire diamond)
635:The combination of
324:Solubility in water
289: g·mol
29:
664:Sodium borohydride
621:
588:sodium borohydride
536:, it is used as a
494:Infobox references
442:Related compounds
399:
27:
774:Organic Syntheses
755:10.1021/op0601013
717:10.1021/jo960057x
711:(11): 3849–3862.
565:COOH → Na[(CH
542:organic synthesis
520:with the formula
518:chemical compound
502:Chemical compound
500:
499:
430:Safety data sheet
176:CompTox Dashboard
100:Interactive image
16:(Redirected from
895:
873:Sodium compounds
858:
857:
851:
843:
832:10.1039/A827395Z
815:
809:
808:
807:(23): 4032–4036.
798:
792:
791:
789:
765:
759:
758:
738:
729:
728:
699:
693:
683:
645:carboxylic acids
642:
601:However, unlike
577:
531:
508:, also known as
484:
478:
475:
474:
419:
412:
405:
390:
346:4 at boron atom
288:
275:
260:Chemical formula
200:
199:
184:
182:
166:
146:
135:
124:
113:
102:
78:
37:
30:
21:
903:
902:
898:
897:
896:
894:
893:
892:
883:Reducing agents
863:
862:
861:
844:
817:
816:
812:
800:
799:
795:
767:
766:
762:
740:
739:
732:
701:
700:
696:
684:
680:
676:
670:
654:
640:
636:
633:
626:
612:
584:
576:
572:
568:
564:
560:
556:
529:
525:
521:
503:
496:
491:
490:
489: ?)
480:
476:
472:
468:
452:
424:
423:
422:
421:
414:
407:
400:
396:
388:
355:
353:Molecular shape
343:
326:
286:
273:
269:
265:
262:
248:
245:
240:
239:
228:
225:
224:
221:
215:
214:
203:
185:
178:
169:
149:
136:
105:
92:
81:
68:
54:
52:
23:
22:
15:
12:
11:
5:
901:
899:
891:
890:
885:
880:
875:
865:
864:
860:
859:
810:
793:
760:
730:
694:
677:
675:
672:
668:
667:
661:
653:
650:
632:
629:
624:
583:
580:
579:
578:
538:reducing agent
501:
498:
497:
492:
470:
469:
465:standard state
462:
459:
458:
453:
447:
444:
443:
439:
438:
433:
426:
425:
415:
408:
401:
386:
385:
384:
383:
381:
372:
371:
367:
366:
356:
351:
348:
347:
344:
339:
336:
335:
331:
330:
329:decomposition
327:
322:
319:
318:
315:
309:
308:
305:
299:
298:
295:
291:
290:
284:
278:
277:
263:
258:
255:
254:
250:
249:
247:
246:
243:
235:
234:
233:
230:
229:
227:
226:
222:
219:
218:
210:
209:
208:
205:
204:
202:
201:
188:
186:
174:
171:
170:
168:
167:
159:
157:
151:
150:
148:
147:
139:
137:
129:
126:
125:
115:
107:
106:
104:
103:
95:
93:
86:
83:
82:
80:
79:
71:
69:
64:
61:
60:
56:
55:
50:
48:
44:
43:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
900:
889:
886:
884:
881:
879:
876:
874:
871:
870:
868:
855:
849:
841:
837:
833:
829:
825:
821:
814:
811:
806:
805:
797:
794:
788:
783:
779:
775:
771:
764:
761:
756:
752:
748:
744:
737:
735:
731:
726:
722:
718:
714:
710:
706:
698:
695:
692:
688:
682:
679:
673:
671:
665:
662:
659:
656:
655:
651:
649:
646:
630:
628:
617:
613:
610:
608:
604:
599:
597:
593:
589:
581:
555:
554:
553:
551:
547:
543:
539:
535:
532:. Like other
519:
515:
511:
507:
495:
488:
483:
466:
460:
457:
454:
451:
446:
445:
440:
437:
436:External MSDS
434:
431:
428:
427:
420:
413:
406:
382:
379:
378:
374:
373:
368:
364:
360:
357:
354:
350:
349:
345:
342:
338:
337:
332:
328:
325:
321:
320:
316:
314:
313:Melting point
311:
310:
306:
304:
301:
300:
297:White powder
296:
293:
292:
285:
283:
280:
279:
264:
261:
257:
256:
251:
242:
238:
231:
217:
213:
206:
198:
194:
193:DTXSID8074368
190:
189:
187:
177:
173:
172:
165:
161:
160:
158:
156:
153:
152:
145:
141:
140:
138:
132:
128:
127:
123:
119:
116:
114:
112:ECHA InfoCard
109:
108:
101:
97:
96:
94:
90:
85:
84:
77:
73:
72:
70:
67:
63:
62:
57:
45:
40:
36:
31:
19:
878:Borohydrides
848:cite journal
823:
819:
813:
802:
796:
777:
773:
763:
746:
742:
708:
704:
697:
681:
669:
634:
622:
611:
600:
585:
546:protonolysis
534:borohydrides
513:
509:
505:
504:
376:
59:Identifiers
47:Other names
550:acetic acid
359:Tetrahedral
294:Appearance
253:Properties
118:100.115.747
867:Categories
826:(6): 395.
749:(5): 971.
674:References
522:Na[(CH
334:Structure
307:1.20 g/cm
282:Molar mass
266:Na[(CH
164:4VU0JE4YSK
87:3D model (
76:56553-60-7
66:CAS Number
804:Synthesis
637:Na[BH
623:NaBH(OAc)
573:BH] + 3 H
557:Na[BH
49:NaBH(OAc)
888:Acetates
840:96906861
725:11667239
652:See also
607:methanol
590:or even
561:] + 3 CH
377:NFPA 704
370:Hazards
144:23676153
516:, is a
487:what is
485: (
303:Density
276:
131:PubChem
838:
780:: 74.
723:
482:verify
479:
450:anions
448:Other
432:(SDS)
287:211.94
237:SMILES
42:Names
836:S2CID
643:with
365:atom
363:boron
212:InChI
89:JSmol
854:link
721:PMID
569:COO)
526:COO)
514:STAB
270:COO)
155:UNII
828:doi
782:doi
751:doi
713:doi
687:doi
540:in
530:BH]
361:at
274:BH]
181:EPA
134:CID
869::
850:}}
846:{{
834:.
824:27
822:.
778:90
776:.
772:.
747:10
745:.
733:^
719:.
709:61
707:.
552::
856:)
842:.
830::
790:.
784::
757:.
753::
727:.
715::
689::
641:]
639:4
625:3
575:2
571:3
567:3
563:3
559:4
528:3
524:3
477:Y
418:2
411:4
404:3
272:3
268:3
183:)
179:(
91:)
51:3
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
