9683. Trifluoromethyltrimethylsilane

Nomenclature

CAS number: 81290-20-2
Trimethyl(trifluoromethyl)silane; Ruppert's reagent; TMS-CF3.
C4H9F3Si; mol wt 142.19.
C 33.79%, H 6.38%, F 40.08%, Si 19.75%.

Description and references

Reagent used for fluoride ion catalyzed trifluoromethylation of organic substrates. Prepn: I. Ruppert et al., Tetrahedron Lett. 25, 2195 (1984); and use in trifluoromethylation of aldehydes and ketones: G. K. S. Prakash et al., J. Am. Chem. Soc. 111, 393 (1989). Review of chemistry: G. K. S. Prakash, A. K. Yudin, Chem. Rev. 97, 757-786 (1997); R. P. Singh, J. M. Shreeve, Tetrahedron 56, 7613-7632 (2000); R. S. Bastos, Synlett 2008, 1425-1426.

Chemical structure

Properties

Colorless, volatile liquid, bp 45° (Ruppert); also reported as bp 54-55° (Prakash, Yudin).

Use

Nucleophilic trifluoromethylating reagent.