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
81290-20-2 YesY
3D model (Jmol) Interactive image
ECHA InfoCard 100.106.346
PubChem 552549
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).
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Infobox references

Trifluoromethyltrimethylsilane (Ruppert's 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

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