Silane, 1,1′-(Chloromethylene)bis[1,1,1]-trimethyl-

Abstract

[5926-35-2] C7H19ClSi2 (MW 194.85) InChI = 1S/C7H19ClSi2/c1-9(2,3)7(8)10(4,5)6/h7H,1-6H3 InChIKey = XNJGZHVYPBNLEB-UHFFFAOYSA-N (versatile C1 building block; broad application in Peterson olefination reactions; Grignard reagent participates readily in Kumada cross-coupling reactions with aryl and vinyl halides; useful in synthesis of methylenephosphine analogs; as sterically demanding ligand for a number of main group and transition metal complexes) Alternative names: chlorobis(trimethylsilyl)methane; bis(trimethylsilyl) methyl chloride; bis(trimethylsilyl)chloromethane; [chloro(trimethylsilyl)methyl]trimethylsilane. Physical Data: bp 57–60 °C (15 mmHg); flash point 48 °C; d 0.892 g mL−1 (25 °C). Solubility: soluble in common organic solvents (DMF, THF, Et2O, CH2Cl2). Form Supplied in: colorless liquid, commercially available. Preparative Method: a convenient one-pot procedure has been developed by Kemp and Cowley in which trimethylsilylchloride reacts with dichloromethane in the presence of nBuLi at −110 °C to give bis(trimethylsilyl)dichloromethane.1 This intermediate is sequentially treated with nBuLi and ethanol to yield chlorobis(trimethylsilyl)methane. A number of other syntheses have been described.2-8 Purification: fractionally distilled through a Vigreaux column.1 Handling, Storage, and Precautions: flammable. Chlorobis(trimethylsilyl)methane is irritating to the eyes, skin, and respiratory system and should only be handled in a well-ventilated fume hood. In addition, proper protective clothing, gloves, and eye/face protection should be worn when title compound is in use. In case of contact with eyes, rinse immediately with water and seek medical advice.