CAS 22206-57-1 Tbaf - Catalysts / Alfa Chemistry

Synonyms

tetra(n-butyl)ammonium fluoride hydrate; UQCWXKSHRQJGPH-UHFFFAOYSA-M; Tetrabutylammonium fluoride xhydrate; TetrabutylammoniumFluorideHydrate; AKOS000119999; KS-00000EBL; FT-0638198; TC-145121; tetra-n-butylammonium fluoride hydrate; BB0295030;

IUPAC Name

tetrabutylazanium;fluoride;hydrate;

Molecular Weight

279.484g/mol

Molecular Formula

C16H38FNO;

Canonical SMILES

CCCC[N+](CCCC)(CCCC)CCCC.O.[F-];

InChI

InChI=1S/C16H36N.FH.H₂O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;/h5-16H2,1-4H3;1H;1H2/q+1;;/p-1;

InChI Key

UQCWXKSHRQJGPH-UHFFFAOYSA-M;

Storage

2-8°C

Complexity

116

Covalently-Bonded Unit Count

Exact Mass

279.294g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

279.294g/mol

Rotatable Bond Count

Topological Polar Surface Area

1A^2

Application

Tbaf serves as a versatile and essential reagent in organic chemistry, appearing as a light greenish to amber or brown solution. It functions as a catalyst for the etherification of alcohols and phenols with alkyl halides, as well as for benzylation reactions. Beyond these applications, Tbaf acts as a key component in various organic synthetic processes including addition, condensation, base-catalyzed cyclization, fluorination, and desulfonylation reactions. Additionally, it is utilized as a deprotecting agent. Commonly dried prior to use to ensure effectiveness, Tbaf is an organic soluble fluoride salt widely employed as a base, a phase transfer catalyst, and a fluoride source. In the development of fluoride sensors, Tbaf is valued as an easy-to-handle and measurable fluoride anion source, with its fluoride ions behaving as free fluorides in solution, showing minimal interaction with the ammonium cation. Furthermore, because Tbaf does not absorb light at wavelengths greater than 240 nm, it is particularly useful for monitoring sensing reactions through visible spectroscopy.

February 11, 2025

Versatile Catalyst for Diverse Reactions

TBAF has been invaluable in our lab, facilitating clean etherification and benzylation reactions. Easy handling and reliable performance make it our go-to reagent for fluorination and deprotection in organic synthesis research. Highly recommended!