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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:
87749-50-6
Molecular Weight:
315.51
Beilstein:
3761900
EC Number:
207-057-2
MDL number:
MFCD00149981
UNSPSC Code:
12352107
PubChem Substance ID:
57653206
NACRES:
NA.22

Quality Level

200

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
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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An Efficient Method for the Production of Terminal Alkynes from 1, 1-Dibromo-1-alkenes and its Application in the Total Synthesis of Natural Product Dihydroxerulin
Liu S, et al.
advanced synthesis and catalysis, 357(2-3), 553-560 (2015)
Tetrabutylammonium fluoride-induced dehydrobromination of vinyl bromides to terminal acetylenes
Okutani M and Mori Y
Tetrahedron Letters, 48(39), 6856-6859 (2007)
T.W. Greene et al.
Protective Groups in Organic Synthesis (1991)
An Efficient Method for the Production of Terminal Alkynes from 1, 1-Dibromo-1-alkenes and its Application in the Total Synthesis of Natural Product Dihydroxerulin
Liu S, et al.
Advanced Synthesis & Catalysis, 357(2-3), 553-560 (2015)
G. Majetich et al.
The Journal of Organic Chemistry, 51, 1745-1745 (1986)
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