250600
Tris(dimethylamino)sulfonium difluorotrimethylsilicate
technical grade
Synonym(s):
TAS-F, TASF, Tris(dimethylamino)sulfur trimethylsilyl difluoride
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About This Item
Linear Formula:
[(CH3)2N]3S[(CH3)3SiF2]
CAS Number:
Molecular Weight:
275.48
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3577020
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
SMILES string
C[Si-](C)(C)(F)F.CN(C)[S+](N(C)C)N(C)C
InChI key
JMGVTLYEFSBAGJ-UHFFFAOYSA-N
grade
technical grade
reaction suitability
reagent type: reductant
storage temp.
2-8°C
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
hcodes
signalword
Danger
Hazard Classifications
Skin Corr. 1B
supp_hazards
Storage Class
8A - Combustible corrosive hazardous materials
wgk
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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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)
Tris (dimethylamino) sulfonium Difluorotrimethylsilicate
RajanBabu TV , et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-12 (2001)
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)
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)
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