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Merck

250600

Sigma-Aldrich

Tris(dimethylamino)sulfonium difluorotrimethylsilicate

technical grade

Sinónimos:

TAS-F, TASF, Tris(dimethylamino)sulfur trimethylsilyl difluoride

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About This Item

Fórmula lineal:
[(CH3)2N]3S[(CH3)3SiF2]
Número de CAS:
Peso molecular:
275.48
Beilstein/REAXYS Number:
3577020
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

reaction suitability

reagent type: reductant

storage temp.

2-8°C

SMILES string

C[Si-](C)(C)(F)F.CN(C)[S+](N(C)C)N(C)C

InChI

1S/C6H18N3S.C3H9F2Si/c1-7(2)10(8(3)4)9(5)6;1-6(2,3,4)5/h1-6H3;1-3H3/q+1;-1

InChI key

JMGVTLYEFSBAGJ-UHFFFAOYSA-N

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General description

Tris(dimethylamino)sulfonium difluorotrimethylsilicate is widely used in organic synthesis as a source of fluoride ion for the synthesis of fluorinated compounds by C-F bond formation. It is also used as a reagent in hydrosilylation, cyanomethylation of ketones and Pd-catalyzed cross-coupling reactions.

Application

Tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF2SiMe3) can be used as a mild deprotecting reagent for the cleavage of silicon protecting groups.
It can also be used
  • To synthesize deoxyfluoro sugars by reacting with trifluoromethanesulfonyl derivatives of partially protected sugars.
  • As a reagent for the fluorination of hydroxyl-containing compounds.

Other Notes

Remainder tris(dimethylamino)sulfonium bifluoride

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

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


Certificados de análisis (COA)

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Stephen R Groskreutz et al.
Journal of chromatography. A, 1523, 193-203 (2017-07-20)
On-column solute focusing is a simple and powerful method to decrease the influence of precolumn band spreading and increase the allowable volume injected increasing sensitivity. It relies on creating conditions so that the retention factor, k', is transiently increased during
Tris (dimethylamino) sulfonium difluorotrimethylsilicate, a mild reagent for the removal of silicon protecting groups
Scheidt KA, et al.
The Journal of Organic Chemistry, 63(19), 6436-6437 (1998)
The rapid synthesis of deoxyfluoro sugars using tris (dimethylamino) sulfonium difluorotrimethylsilicate (TASF)
Doboszewski B, et al.
Canadian Journal of Chemistry, 65(2), 412-419 (1987)
Utility of tris(dimethylamino)sulphonium difluorotrimethylsilicate (TASF) for the rapid synthesis of deoxyfluoro sugars
Walter A. Szarek, et al.
Journal of the Chemical Society. Chemical Communications, 663-663 (1985)
Tris (dimethylamino) sulfonium Difluorotrimethylsilicate
RajanBabu TV , et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-12 (2001)

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