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441457

Sigma-Aldrich

Tetrabutylammonium difluorotriphenylsilicate

97%

Synonym(s):

TBAT

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N[(C6H5)3SiF2]
CAS Number:
163931-61-1
Molecular Weight:
539.86
MDL number:
MFCD00274218
UNSPSC Code:
12352116
PubChem Substance ID:
24867661
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
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Yansheng Wang et al.
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Tetrabutylammonium Difluorotriphenylsilicate (TBAT )
Simpkins NS, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-14 (2001)
Journal of the American Chemical Society, 117, 5166-5166 (1995)
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