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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/REAXYS Number:
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

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


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Fluorodenitrations using tetrabutylammonium fluoride.
Clark JH and Smith DK.
Tetrahedron Letters, 26(18), 2233-2236 (1985)
Beatriz A P Ass et al.
Macromolecular bioscience, 4(11), 1008-1013 (2004-11-06)
The novel solvent dimethyl sulfoxide (DMSO)/tetrabutylammonium fluoride trihydrate (TBAF . 3H(2)O) was studied for acetylation of linters cellulose. In order to control the degree of substitution (DS), acetylation of the macromolecule was carried out at different reaction time and temperature
Effective preparation of cellulose derivatives in a new simple cellulose solvent.
Heinze T, et al.
Macromolecular Chemistry and Physics, 201(6), 627-631 (2000)
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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