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Sigma-Aldrich

Tetrabutylammonium difluorotriphenylsilicate

97%

Synonym(s):

TBAT

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N[(C6H5)3SiF2]
CAS Number:
Molecular Weight:
539.86
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

solid

mp

157-163 °C (lit.)

SMILES string

CCCC[N+](CCCC)(CCCC)CCCC.F[Si-](F)(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C18H15F2Si.C16H36N/c19-21(20,16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h1-15H;5-16H2,1-4H3/q-1;+1

InChI key

RQBKGJOQACIQDG-UHFFFAOYSA-N

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General description

Tetrabutylammonium difluorotriphenylsilicate (TBAT) is a non-hygroscopic, organic soluble fluoride source and it is very effective for nucleophilic displacement reactions. Furthermore, TBAT is used as a catalytic promoter.

Application

A fluoride source for nucleophilic fluorination.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

Storage Class

8A - Combustible corrosive hazardous materials

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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Tetrabutylammonium Difluorotriphenylsilicate (TBAT )
Simpkins NS, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-14 (2001)
Kohei Fuchibe et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(12), 2831-2838 (2016-12-03)
Silyl dienol ethers, prepared from α,β-unsaturated ketones, underwent proton sponge-catalyzed difluorocyclopropanation with trimethylsilyl 2,2-difluoro-2-fluorosulfonylacetate in a regioselective manner, leading to 1,1-difluoro-2-siloxy-2-vinylcyclopropanes in good yields. The cyclopropanes thus obtained were in turn subjected to fluoride-ion-catalyzed ring opening to afford 1-fluorovinyl vinyl
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