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86843

Sigma-Aldrich

Tetrabutylammonium fluoride trihydrate

technical, ≥90% (T)

Synonym(s):

TBAF

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About This Item

Linear Formula:
[CH3(CH2)3]4NF · 3H2O
CAS Number:
Molecular Weight:
315.51
Beilstein:
3761900
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

grade

technical

Quality Level

Assay

≥90% (T)

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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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 may be used in the following studies:
  • Synthesis of novel 3-O-(2-methoxyethyl)cellulose.
  • To compose the novel solvent dimethyl sulfoxide (DMSO) /tetrabutylammonium fluoride trihydrate, used for the acetylation of linters cellulose.
  • Synthesis of neutral organometallic fluoro complex.
  • Synthesis of fluoroaromatic compounds.

Pictograms

Health hazardExclamation mark

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

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Fluorodenitrations using tetrabutylammonium fluoride.
Clark JH and Smith DK.
Tetrahedron Letters, 26(18), 2233-2236 (1985)
Laurent Coue et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 10(8), 1906-1912 (2004-04-14)
The reaction of the complex [Mo(OTf)(eta(3)-C(3)H(4)-Me-2)(CO)(2)(phen)] (1) (OTf = trifluoromethylsulfonate; phen = 1,10-phenanthroline) with tetrabutylammonium fluoride trihydrate afforded the fluoride complex [MoF(eta(3)-C(3)H(4)-Me-2)(CO)(2)(phen)] (2). The IR spectrum and the oxidation potential of 2 reflect the fact that its metal center is
Thomas Heinze et al.
Carbohydrate research, 343(4), 668-673 (2008-02-12)
The synthesis of novel 3-O-(2-methoxyethyl)cellulose via 2,6-di-O-thexyldimethylsilyl ethers was successfully carried out. Treatments of 3-O-(2-methoxyethyl)-2,6-di-O-thexyldimethylsilylcellulose with tetrabutylammonium fluoride trihydrate led to a complete removal of the protecting groups. Structure characterization carried out by means of 1D and 2D NMR spectroscopy
Tetrabutylammonium Fluoride.
Li HY, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2007)
New solvents for cellulose: dimethyl sulfoxide/ammonium fluorides.
Kohler S and Heinze T.
Macromolecular Bioscience, 7(3), 307-314 (2007)

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