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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:
87749-50-6
Molecular Weight:
315.51
Beilstein:
3761900
EC Number:
207-057-2
MDL number:
MFCD00149981
UNSPSC Code:
12352116
PubChem Substance ID:
329769494
NACRES:
NA.22

grade

technical

Quality Level

200

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
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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD2701
BCCB7048
BCBW3823
BCBW2570
BCBW0223

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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
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)
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