250600
Tris(dimethylamino)sulfonium difluorotrimethylsilicate
technical grade
Synonym(s):
TAS-F, TASF, Tris(dimethylamino)sulfur trimethylsilyl difluoride
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About This Item
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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
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
Supplementary Hazards
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
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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
The Journal of Organic Chemistry, 63(19), 6436-6437 (1998)
Tris (dimethylamino) sulfonium Difluorotrimethylsilicate
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-12 (2001)
The rapid synthesis of deoxyfluoro sugars using tris (dimethylamino) sulfonium difluorotrimethylsilicate (TASF)
Canadian Journal of Chemistry, 65(2), 412-419 (1987)
Utility of tris(dimethylamino)sulphonium difluorotrimethylsilicate (TASF) for the rapid synthesis of deoxyfluoro sugars
Journal of the Chemical Society. Chemical Communications, 663-663 (1985)
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