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Trifluoromethyltrimethylsilane

Trifluoromethyltrimethylsilane
Skeletal formula of trifluoromethyltrimethylsilane
Ball-and-stick model of the trifluoromethyltrimethylsilane molecule
Names
IUPAC name
Trimethyl(trifluoromethyl)silane
Other names
Ruppert's reagent; TFMTMS; CF3SiMe3
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.106.346
PubChem CID
Properties
C4H9F3Si
Molar mass 142.20 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Trifluoromethyltrimethylsilane (Ruppert's reagent) is an organosilicon compound with the formula CF3Si(CH3)3. It is a colorless liquid. The compound is a reagent used in organic chemistry for the introduction of the trifluoromethyl group. The compound was first prepared in 1984 by Ingo Ruppert and further popularized by G. K. Surya Prakash.

The reagent is prepared from trimethylsilyl chloride and bromotrifluoromethane in the presence of a phosphorus(III) reagent that serves as a halogen acceptor.

In the presence of a source of fluoride, the reagent forms the -ate complex [CF3Si(CH3)3F]. This species attacks aldehydes and ketones. The net reaction is insertion of the carbonyl into the Si-CF3 bond to give a trimethylsilyl ether. Hydrolysis the gives trifluoromethyl methanols. A typical fluoride-containing catalyst is tetrabutylammonium fluoride. It converts esters to trifluoromethyl ketones.

The reagent has largely supplanted trifluoromethyllithium, which is not isolable and rapidly decomposes to yield lithium fluoride and difluorocarbene.


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