10397. Chlorotriethylsilane

Nomenclature

CAS number: 994-30-9
Triethylchlorosilane; triethylsilyl chloride; TESCl; Et3SiCl.
C6H15ClSi; mol wt 150.72.
C 47.81%, H 10.03%, Cl 23.52%, Si 18.63%.

Description and references

Silylating reagent used in organic synthesis to introduce the triethylsilyl (TES) protecting group. Prepn from triethylethoxysilane: A. Ladenburg, Ann. 164, 300 (1872); from hexaethyldisiloxane: P. A. Di Giorgio et al., J. Am. Chem. Soc. 68, 1380 (1946) DOI; from β-chloroethyltriethylsilane: L. H. Sommer, ibid. 70, 2869 (1948) DOI. Use in protection of hydroxyl groups: W. Oppolzer et al., Helv. Chim. Acta 64, 2002 (1981) DOI; W. R. Roush, S. Russo-Rodriguez, J. Org. Chem. 52, 598 (1987) DOI. Additional synthetic applications: S. Danishefsky et al., J. Am. Chem. Soc. 107, 1285 (1985) DOI; Y. Fujii et al., J. Organomet. Chem. 692, 375 (2007) DOI. Review: E. Turos in Encyclopedia of Reagents for Organic Synthesis 2, L. A. Paquette, Ed. (Wiley, New York, 1995) pp 1225-1227.

Chemical structure

Properties

Liquid. bp 144-147°. d20 0.8967. nD20 1.4314. Flammable. Corrosive. Reacts violently with water. Flash point, closed cup: 86°F (30°C). Sol in most aprotic solvents.

Use

Reagent in synthetic organic chemistry.