10372. Triethylsilane

Nomenclature

CAS number: 617-86-7
Triethylhydrosilane; triethylsilicon hydride; TES.
C6H16Si; mol wt 116.28.
C 61.97%, H 13.87%, Si 24.15%.

Description and references

Versatile organosilicon hydride reducing agent; used in silylations, radical chain reactions, and transfer hydrogenations. Prepn: A. Ladenburg, Ann. 164, 300 (1872); C. A. Kraus, W. K. Nelson, J. Am. Chem. Soc. 56, 195 (1934) DOI; and physical properties: S. Tannenbaum et al., ibid. 75, 3753 (1953) DOI. Synthetic applications: M. P. Doyle et al., J. Org. Chem. 55, 6082 (1990) DOI; S. J. Cole et al., J. Chem. Soc. Perkin Trans. 1 1991, 103 DOI; V. Gevorgyan et al., J. Org. Chem. 66, 1672 (2001) DOI PubMed; P. K. Mandal, J. S. McMurray, ibid. 72, 6599 (2007) DOI PubMed. Reviews: J. L. Fry in Encyclopedia of Reagents for Organic Synthesis 7, L. A. Paquette, Ed. (Wiley, New York, 1995) pp 5118-5122; J. de Almeida Rodrigues Jr., Synlett 2008, 3249-3250 DOI.

Chemical structure

Properties

Colorless liquid with faint garlic-like odor. Flammable. Irritant. fp 156.90. bp 108.77°. d20 0.7318. nD20 1.4119. Flash pt, closed cup: 26.6°F (3.0°C). Sol in most organic solvents. Insol in water.

Use

Reagent in synthetic organic chemistry.