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86872

Sigma-Aldrich

Tetrabutylammonium fluoride trihydrate

≥97.0% (NT)

Synonym(s):

TBAF

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About This Item

Linear Formula:
[CH3(CH2)3]4NF · 3H2O
CAS Number:
Molecular Weight:
315.51
Beilstein/REAXYS Number:
3761900
EC Number:
MDL number:
UNSPSC Code:
12352107
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97.0% (NT)

form

crystals

mp

62-63 °C (lit.)

SMILES string

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

InChI

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

InChI key

VEPTXBCIDSFGBF-UHFFFAOYSA-M

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General description

Tetrabutylammonium fluoride trihydrate is a mild base used in reactions like aldol-type condensation reactions, Michael-type reactions, ring-opening reactions. Its is also used as a promoter in cross-coupling reactions and cyclization of carbocycles and heterocycles.

Application

Reactant for:
Preparation of deprotecting agents in preparation of cellulose derivatives
Synthesis of lipophilic peptides for DNA transfections in vivo
Dehydrobromination reactions
Tetrabutylammonium fluoride trihydrate can be used as a base:
  • For the dehydrobromination of vinyl bromides to terminal acetylenes.
  • In the conversion of 1,1-dibromo-1-alkenes to terminal alkynes via Corey–Fuchs reaction.
  • In Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryltrialkoxysilanes in the presence of a palladium catalyst.

It can be used to catalyze ethynylation of quinolines and isoquinolines using calcium carbide in aqueous N,N-dimethylacetamide.

Other Notes

Reagent for the cleavage of silyl ethers and other silyl protecting groups; Catalyst for various reactions with silicon compounds; Use as a base in organic synthesis; Instability of anhydrous TBAF

pictograms

Health hazardExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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Tetrabutylammonium fluoride-induced dehydrobromination of vinyl bromides to terminal acetylenes
Okutani M and Mori Y
Tetrahedron Letters, 48(39), 6856-6859 (2007)
D. Albanese et al.
Synthesis, 34-34 (1994)
Ethynylation of Isoquinoline and Quinoline Derivatives with Calcium Carbide
Samzadeh-Kermani A
Synlett, 28(16), 2126-2130 (2017)
T.W. Greene et al.
Protective Groups in Organic Synthesis (1991)
A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides
Yuen OY, et al.
Chemistry?A European Journal , 22(19), 6471-6476 (2016)

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