Trifluoromethyltrimethylsilane
 | |
| Names | |
|---|---|
| IUPAC name
Trimethyl(trifluoromethyl)silane | |
| Other names
Ruppert's Reagent; TFMTMS | |
| Identifiers | |
81290-20-2  | |
| Jmol-3D images | Image |
| PubChem | 552549 |
| |
| Properties | |
| Molecular formula |
C4H9F3Si |
| Molar mass | 142.19 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.9626 g/cm3 at 20 °C |
| Boiling point | 54 to 55 °C (129 to 131 °F; 327 to 328 K) |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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 methanols 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 (3): 757–86. doi:10.1021/cr9408991. PMID 11848888.