Misplaced Pages

TASF reagent: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editNext edit →Content deleted Content addedVisualWikitext
Revision as of 23:43, 14 December 2014 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified and watched fields - added verified revid - updated 'CASNo_Ref', 'Verifiedfields', 'Watchedfields', 'verifiedrevid') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|e...← Previous edit Revision as of 14:11, 4 May 2015 edit undoJynto (talk | contribs)Extended confirmed users3,197 edits Adding ball-and-stick model, adding alt text, adjusting image sizeNext edit →
Line 4: Line 4:
| verifiedrevid = 470482160 | verifiedrevid = 470482160
| ImageFile = TASF.png | ImageFile = TASF.png
| ImageSize = | ImageSize = 260
| ImageAlt = Skeletal formulas of the TASF reagent
| ImageFile1 = TASF reagent 3D ball.png
| ImageSize1 = 260
| ImageAlt1 = Ball-and-stick models of the component ions of the TASF reagent
| IUPACName = Tris(dimethylamino)sulfonium difluorotrimethylsilicate | IUPACName = Tris(dimethylamino)sulfonium difluorotrimethylsilicate
| OtherNames = | OtherNames =

Revision as of 14:11, 4 May 2015

TASF reagent
Skeletal formulas of the TASF reagent
Ball-and-stick models of the component ions of the 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 to 101 °C (208 to 214 °F; 371 to 374 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) 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.
Categories: