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Sigma-Aldrich

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:
59218-87-0
Molecular Weight:
275.48
Beilstein:
3577020
MDL number:
MFCD00012170
UNSPSC Code:
12352101
PubChem Substance ID:
24855064
NACRES:
NA.22
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grade

technical grade

Quality Level

100

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.[1]

Application

Tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF2SiMe3) can be used as a mild deprotecting reagent for the cleavage of silicon protecting groups.[2]
It can also be used
  • To synthesize deoxyfluoro sugars by reacting with trifluoromethanesulfonyl derivatives of partially protected sugars.[3]
  • As a reagent for the fluorination of hydroxyl-containing compounds.[4]

Other Notes

Remainder tris(dimethylamino)sulfonium bifluoride

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR1491
SHBL2184
SHBJ4688
SHBG5349V
SHBC7084V

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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)
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)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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