276:
201:
402:
39:
566:
in organic solvents. As a fluoride ion source, TBAF solves this problem, although the nature of the fluoride is uncertain because TBAF samples are almost always hydrated, resulting in the formation of bifluoride
761:
K. Hiroya; R. Jouka; M. Kameda; A. Yasuhara & T. Sakamoto (2001). "Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride".
589:. As a deprotecting agent, TBAF in DMSO will convert O-silylated enolates into carbonyls. With C-Si bonds, TBAF gives carbanions that can be trapped with electrophiles or undergo protonolysis.
534:
salt. Similarly, samples dried at 40 °C under high vacuum still contain 10-30 mol% of water and some 10% of difluoride. Instead, anhydrous TBAF has been prepared by the reaction of
675:
D. Phillip Cox; Jacek
Terpinski; Witold Lawrynowicz (1984). "'Anhydrous' tetrabutylammonium fluoride: a mild but highly efficient source of nucleophilic fluoride ion".
740:
Nina
Gommermann and Paul Knochel "N,N-Dibenzyl-N--amine from Cyclohexanecarbaldehyde, Trimethylsilylacetylene and Dibenzylamine" Org. Synth. 2007, 84, 1.
415:
613:
325:
410:
17:
706:
138:
809:
630:
794:
290:
422:
571:) hydroxide (OH) as well as fluoride. Many applications tolerate heterogeneous or ill-defined fluoride sources.
611:
Li, Hui-Yin; Sun, Haoran; DiMagno, Stephen G. (2007). "Tetrabutylammonium
Fluoride". In Paquette, Leo A. (ed.).
677:
648:
530:. However, heating samples of the hydrated material to 77 °C under vacuum causes decomposition to the
233:
196:
158:
254:
505:
804:
271:
646:
Ramesh K. Sharma; James L. Fry (1983). "Instability of anhydrous tetra-n-alkylammonium fluorides".
457:
582:
763:
520:
178:
242:
113:
51:
8:
531:
299:
InChI=1S/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
106:
96:
508:. Upon evaporation of the water, TBAF can be collected as an oil in quantitative yield.
309:
InChI=1/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
275:
200:
799:
543:
501:
776:
723:
704:
626:
622:
535:
497:
480:
NF. It is commercially available as the white solid trihydrate and as a solution in
222:
772:
741:
715:
686:
657:
618:
586:
578:
348:
527:
481:
674:
393:
788:
745:
559:
381:
189:
727:
539:
575:
690:
661:
563:
371:
169:
719:
386:
58 to 60 °C (136 to 140 °F; 331 to 333 K) (trihydrate)
760:
512:
392:
Except where otherwise noted, data are given for materials in their
555:
516:
485:
137:
574:
As a fluoride source in organic solvents, TBAF is used to remove
209:
149:
127:
703:
645:
259:
538:
and tetrabutylammonium cyanide. Solutions of the salt in
562:
acceptor, its salts tend to be hydrated and of limited
38:
786:
221:
112:
105:
614:Encyclopedia of Reagents for Organic Synthesis
491:
610:
515:samples is of interest as the basicity of
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199:
177:
241:
707:Journal of the American Chemical Society
606:
604:
602:
270:
14:
787:
697:
190:
639:
549:
302:Key: FPGGTKZVZWFYPV-UHFFFAOYSA-M
157:
599:
312:Key: FPGGTKZVZWFYPV-REWHXWOFAO
212:
76:Tetrabutylammonium fluoride; TBAF;
24:
754:
668:
25:
821:
526:units on passing from aqueous to
67:-Tributylbutan-1-aminium fluoride
623:10.1002/9780470842898.rt015.pub2
496:TBAF can be prepared by passing
400:
37:
484:. TBAF is used as a source of
396:(at 25 °C , 100 kPa).
810:Reagents for organic chemistry
734:
13:
1:
777:10.1016/S0040-4020(01)00991-7
592:
460:with the chemical formula (CH
678:Journal of Organic Chemistry
649:Journal of Organic Chemistry
7:
18:Tetrabutylammonium fluoride
10:
826:
519:increases by more than 20
506:tetrabutylammonium bromide
492:Preparation and properties
441:, commonly abbreviated to
376:261.46 g/mol
617:. John Wiley & Sons.
488:ion in organic solvents.
390:
341:
321:
286:
89:
73:
50:
45:
36:
795:Tetrabutylammonium salts
746:10.15227/orgsyn.084.0001
458:quaternary ammonium salt
32:-butylammonium fluoride
583:phase transfer catalyst
581:. It is also used as a
439:-butylammonium fluoride
558:ion is such a strong
333:.CCCC(CCCC)(CCCC)CCCC
52:Preferred IUPAC name
691:10.1021/jo00191a035
662:10.1021/jo00160a041
532:hydrogen difluoride
33:
550:Reactions and uses
544:dimethyl sulfoxide
502:ion-exchange resin
423:Infobox references
117: (trihydrate)
27:
720:10.1021/ja0440497
579:protecting groups
536:hexafluorobenzene
498:hydrofluoric acid
431:Chemical compound
429:
428:
255:CompTox Dashboard
139:Interactive image
16:(Redirected from
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805:Nonmetal halides
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771:(48): 9697–710.
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349:Chemical formula
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528:aprotic solvent
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482:tetrahydrofuran
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685:(17): 3216–9.
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656:(12): 2112–4.
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632:978-0471936237
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585:and as a mild
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504:, followed by
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714:(7): 2050–1.
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560:hydrogen bond
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382:Melting point
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554:Because the
553:
546:are stable.
540:acetonitrile
522:
510:
495:
447:
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442:
436:
434:
433:
90:Identifiers
77:
74:Other names
64:
60:
56:
29:
764:Tetrahedron
576:silyl ether
500:through an
342:Properties
197:100.006.417
789:Categories
593:References
564:solubility
511:Preparing
372:Molar mass
243:2618F0C37I
170:ChemSpider
126:3D model (
114:87749-50-6
97:CAS Number
800:Fluorides
513:anhydrous
366:NF
728:15713075
556:fluoride
517:fluoride
486:fluoride
107:429-41-4
456:, is a
416:what is
414: (
223:2724141
210:PubChem
179:2006300
726:
629:
435:Tetra-
411:verify
408:
326:SMILES
150:ChEMBL
46:Names
28:Tetra-
291:InChI
128:JSmol
724:PMID
627:ISBN
587:base
542:and
445:and
443:TBAF
234:UNII
773:doi
742:doi
716:doi
712:127
687:doi
658:doi
619:doi
567:(HF
450:-Bu
260:EPA
213:CID
80:-Bu
791::
769:57
767:.
722:.
710:.
683:49
681:.
654:48
652:.
625:.
601:^
472:CH
468:CH
464:CH
454:NF
354:(C
84:NF
781:.
779:.
775::
744::
730:.
718::
693:.
689::
664:.
660::
635:.
621::
569:2
523:K
521:p
478:4
476:)
474:2
470:2
466:2
462:3
452:4
448:n
437:n
406:N
364:4
362:)
360:9
358:H
356:4
262:)
258:(
130:)
82:4
78:n
65:N
63:,
61:N
59:,
57:N
30:n
20:)
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