10335. Allyltrimethylsilane

Nomenclature

CAS number: 762-72-1
Trimethyl-2-propen-1-ylsilane; trimethylallylsilane; 3-(trimethylsilyl)propene.
C6H14Si; mol wt 114.26.
C 63.07%, H 12.35%, Si 24.58%.

Description and references

Nucleophilic reagent used to introduce allyl group functionality onto organic compds. Prepn from allylmagnesium bromide and trimethylchlorosilane: L. H. Sommer et al., J. Am. Chem. Soc. 70, 2872 (1948) DOI; from methylmagnesium bromide and allyltrichlorosilane: C. A. Burkhard, ibid. 72, 1078 (1950) DOI. NMR spectroscopy studies: L. Delmulle, G. P. Van Der Kelen, J. Mol. Struct. 66, 315 (1980) DOI. Synthetic applications: A. Hosomi, H. Sakurai, Tetrahedron Lett. 17, 1295 (1976) DOI; idem et al., ibid. 19, 3043 (1978) DOI; J. R. Hwu et al., Appl. Organomet. Chem. 11, 381 (1997) DOI; M. E. Jung, A. Maderna, Tetrahedron Lett. 45, 5301 (2004) DOI. Reviews: I. Fleming in Encyclopedia of Reagents for Organic Synthesis 1, L. A. Paquette, Ed. (John Wiley & Sons, New York, 1995) pp 133-136; P. K. Kalita, Synlett 2008, 2080-2081 DOI.

Chemical structure

Properties

Colorless liquid. bp760 85-86°; bp737 84.9°. d20 0.7193. nD20 1.4074. Flammable. Irritant. Flash pt, closed cup: 60.8°F (16°C). Freely sol in all organic solvents.

Use

Reagent in synthetic organic chemistry.