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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:
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
form:
crystals
Assay:
≥97.0% (NT)

Quality Level

200

Assay

≥97.0% (NT)

form

crystals

mp

62-63 °C (lit.)

functional group

amine

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

86872-50G:
86872-10G:
86872-BULK:
86872-250G:
86872-INTR:
86872-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3110
BCCK2214
BCCJ7325
BCCF9682
BCBW7403

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T.W. Greene et al.
Protective Groups in Organic Synthesis (1991)
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)
G. Majetich et al.
The Journal of Organic Chemistry, 51, 1745-1745 (1986)
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