Title: Tetrabutylammonium Fluoride
CAS Registry Number: 429-41-4
CAS Name: N,N,N-Tributyl-1-butanaminium fluoride
Synonyms: TBAF
Molecular Formula: C16H36FN
Molecular Weight: 261.46
Percent Composition: C 73.50%, H 13.88%, F 7.27%, N 5.36%
Literature References: Catalytic reagent which is both a potent base and a source of nucleophilic fluoride. Prepn as hydrated form: D. L. Fowler
et al., J. Am. Chem. Soc. 62, 1140 (1940). Instability of anhydrous form: R. K. Sharma, J. L. Fry,
J. Org. Chem. 48, 2112 (1983). Use as fluoride source: D. P. Cox
et al., ibid. 49, 3216 (1984); T. Kobayashi
et al., ibid. 67, 3156 (2002). Synthesis and/or use as catalyst in cyclization reactions: J. Pless,
ibid. 39, 2644 (1974); A. R. Gangloff
et al., Tetrahedron Lett. 42, 1441 (2001); in addition reactions: P. Molina
et al., Synlett 2003, 714. Deprotecting agent: M. Namikoshi
et al., J. Org. Chem. 56, 5464 (1991); J. J. Parlow
et al., Bioorg. Med. Chem. Lett. 8, 2391 (1998). Brief review in cleavage of silyl protecting groups: M. B. Kumar,
Synlett 2002, 2125-2126.
Properties: Colorless oil which crystallizes on exposure to humidity.
Use: Reagent in organic syntheses in addition, condensation, base-catalyzed cyclization reactions, fluorination and desulfonylation reactions and as a deprotecting agent. Typically dried prior to use.
