Thursday, June 7, 2012 at 9:54AM
Drew Wolfe

Tetramethylsilane

"Tetramethylsilane (abbreviated as TMS) is the chemical compound with the formula Si(CH3)4. It is the simplest tetraorganosilane. Like all silanes, the TMS framework is tetrahedral. TMS is a building block in organometallic chemistry but also finds use in diverse niche applications."

"TMS is a by-product of the production of methyl chlorosilanes, SiClx(CH3)4−x, via the direct process of reacting methyl chloride with silicon. The more useful products of this reaction are those for x = 1, 2, and 3."

"TMS undergoes deprotonation upon treatment with butyllithium to give (H3C)3SiCH2Li. The latter, trimethylsilylmethyl lithium, is a relatively common alkylating agent."

Tetramethylsilane is the accepted internal standard for calibrating chemical shift for 1H13C and 29Si NMR spectroscopy in organic solvents (where TMS is soluble). In water, where it is not soluble, sodium salts of DSS, 2,2-dimethyl-2-silapentane-5-sulfonate, are used instead. Because of its high volatility, TMS can easily be evaporated, which is convenient for recovery of samples analyzed by NMR spectroscopy.

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