Trimethylsilyl chloride

Trimethylsilyl chloride, also known as TMS chloride or trimethylchlorosilane, is a chemical compound of silicon, chlorine, and organic methyl groups. It has the chemical formula Si(CH3)3Cl. It is mostly used in organic synthesis as a source of the trimethylsilyl group.

Preparation

Trimethylsilyl chloride is one of several related compounds (methylchlorosilanes) made in the direct process using methyl chloride and elemental silicon. This reaction can use a catalyst that mostly makes trimethylsilyl chloride, but it is normally made as a byproduct of using the process to make dimethyldichlorosilane.

Uses

Trimethylsilyl chloride reacts with many different organic functional groups, especially in basic environments. The base removes a labile hydrogen atom, which is replaced by trimethylsilyl with chloride as a leaving group. Trimethylsilyl is very bulky, making this a good protecting group for acidic hydrogen in groups like alcohols, primary or secondary amines, carboxylic acids, and terminal alkynes.

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