10311. Chlorotrimethylsilane

Nomenclature

CAS number: 75-77-4
trimethylchlorosilane; trimethylsilane chloride; trimethylsilicon chloride; trimethylsilyl chloride.
C3H9ClSi; mol wt 108.64.
C 33.17%, H 8.35%, Cl 32.63%, Si 25.85%.

Description and references

Silylating reagent and Lewis acid catalyst in synthetic organic chemistry. Prepn from trimethylsilane and chlorine: A. G. Taylor, B. V. De G. Walden, J. Am. Chem. Soc. 66, 842 (1944) DOI; from silicon chloride: H. S. Booth, J. F. Suttle, ibid. 68, 2658 (1946) DOI; from hexamethyldisiloxane and ammonium chloride: B. O. Pray et al., ibid. 70, 433 (1948) DOI. Crystal structure: J. Buschmann et al., Acta Crystallogr. C56, 121 (2000) DOI. Thermodynamic studies: A. E. Beezer, C. T. Mortimer, J. Chem. Soc. A 1966, 514 DOI. Synthetic applications: G. A. Olah et al., J. Org. Chem. 44, 4272 (1979) DOI; J. G. Lee et al., Tetrahedron Lett. 31, 6677 (1990) DOI; J.-M. Lin, B.-S. Liu, Synth. Commun. 27, 739 (1997) DOI; J. Eras et al., J. Org. Chem. 67, 8631 (2002) DOI PubMed; in catalysis: P. Verma, S. Ray, Indian J. Chem. 29B, 652 (1990); L.-W. Xu et al., Synth. Commun. 37, 3095 (2007) DOI. Derivitization and gas chromatography: J. Eras et al., J. Chromatogr. A 1047, 157 (2004) DOI PubMed.

Chemical structure

Properties

Colorless liquid. Strong camphor-like odor. Fumes slightly in air. Flammable. Corrosive. Reacts violently with water. bp 57.3°. fp 57.7° (Booth, Suttle); also reported as fp 40° (Taylor, Walden); mp 97.15° (Buschmann). d425 0.846; d20 0.8581. nD20 1.3884. Flash point, closed cup: 0.4°F (18°C). Heat of formation: 91.9±0.8 kcal/mol.

Use

Reagent to introduce the trimethylsilyl group in organic synthesis. Catalyst. In compd derivitization to increase volatility for analysis by gas chromatography. In prepn of anhydrous solns of hydrochloric acid.