Trifluoromethyltrimethylsilane

Trifluoromethyltrimethylsilane

Names
IUPAC name Trimethyl(trifluoromethyl)silane
Other names Ruppert's Reagent; TFMTMS
Identifiers
CAS Number	81290-20-2
Jmol interactive 3D	Image
PubChem	552549
SMILES C[Si](C)(C)C(F)(F)F
Properties
Chemical formula	C4H9F3Si
Molar mass	142.20 g·mol^−1
Appearance	colorless liquid
Density	0.9626 g/cm^3 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 (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.