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TASF reagent: Difference between revisions

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Revision as of 14:26, 7 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChemSpiderID PubChem InChI1 InChIKey1 SMILES.← Previous edit Revision as of 13:50, 10 December 2010 edit undoBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.Next edit →
Line 6: Line 6:
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID = 7971333 | ChemSpiderID = 7971333
| InChI1 = 1/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 = 1/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
| InChIKey1 = JMGVTLYEFSBAGJ-UHFFFAOYAE | InChIKey = JMGVTLYEFSBAGJ-UHFFFAOYAE
| StdInChI = 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
| StdInChIKey = JMGVTLYEFSBAGJ-UHFFFAOYSA-N
| CASNo = 59218-87-0 | CASNo = 59218-87-0
| PubChem = 9795567 | PubChem = 9795567

Revision as of 13:50, 10 December 2010

TASF reagent
Names
IUPAC name Tris(dimethylamino)sulfonium difluorotrimethylsilicate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.426 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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;-1Key: JMGVTLYEFSBAGJ-UHFFFAOYSA-N
  • InChI=1/C6H18N3S.C3H9F2Si/c1-7(2)10(8(3)4)9(5)6;1-6(2,3,4)5/h1-6H3;1-3H3/q+1;-1Key: JMGVTLYEFSBAGJ-UHFFFAOYAE
SMILES
  • F(F)(C)(C)C.N((N(C)C)N(C)C)(C)C
Properties
Chemical formula C9H27F2N3SSi
Molar mass 275.48
Appearance Colorless solid
Melting point 98-101 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

The TASF reagent or tris(dimethylamino)sulfonium difluorotrimethylsilicate is a reagent in organic chemistry with structural formula . It is an anhydrous source of fluoride and is used to cleave silyl ether protective groups. Many other fluoride reagents are known, but few are truly anhydrous, because of the extraordinary basicity of "naked" F. In TASF, the fluoride is masked as an adduct with the weak Lewis acid trimethylsilylfluoride (FSi(CH3)3). The sulfonium cation ((CH3)2N)3S is unusually non-electrophilic due to the electron-donating properties of the three (CH3)2N substituents.

This compound is prepared from sulfur tetrafluoride:

3 (CH3)2NSi(CH3)3 + SF4 → 2 (CH3)3SiF +

The colorless salt precipitates from the reaction solvent, diethyl ether.

References

  1. W. J. Middleton (1990). "Tris(dimethylamino)sulfonium difluorotrimethylsilicate". Organic Syntheses; Collected Volumes, vol. 7, p. 528.
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