This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 17:53, 11 April 2011 (Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.
Revision as of 17:53, 11 April 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation ()(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
| |
| Names | |
|---|---|
| IUPAC name Trimethyl(trifluoromethyl)silane | |
| Other names Ruppert's Reagent; TFMTMS | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ECHA InfoCard | 100.106.346 
|
| PubChem CID | |
| CompTox Dashboard (EPA) | |
SMILES
| |
| Properties | |
| Chemical formula | C4H9F3Si |
| Molar mass | 142.196 g·mol |
| Appearance | colorless liquid |
| Density | 0.9626 g/cm @ 20 °C |
| Boiling point | 54-55 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
| |
Trifluoromethyltrimethylsilane (often called Ruppert's reagent or Ruppert-Prakash reagent) is a reagent used in organic chemistry for the introduction of the trifluoromethyl group. The compound was first prepared in 1984 in Ingo Ruppert's group at the University of Bonn and introduced into the vocabulary of organic chemistry by the group of Surya Prakash at the University of Southern California five years later.
Use
Upon treatment with a source of fluoride the compound forms an -ate complex that attacks aldehydes and ketones to form trifluoromethyl carbinols and esters to form trifluoromethyl ketones. It is thus a substitute for trifluoromethyllithium, which, unlike higher perfluoroalkyllithium compounds, is not isolable since even at low temperature it rapidly decomposes to yield lithium fluoride and difluorocarbene.
References
- G. K. Surya Prakash; Andrei K. Yudin (1997). "Perfluoroalkylation with Organosilicon Reagents". Chem. Rev. 97: 757–86. doi:10.1021/cr9408991. PMID 11848888.
{{cite journal}}: CS1 maint: multiple names: authors list (link)