Trimethylsilylamine

Trimethylsilylamine, also known as bis(trimethylsilyl)amine or (TMS)2NH, is an organosilicon compound with the chemical formula [(CH3)3Si]2NH. It is a colorless liquid with a pungent odor and is highly reactive. This compound is often used as a silylating agent in organic synthesis. Silylation is a process where a silyl group, such as the trimethylsilyl group, is introduced into an organic molecule. This can alter the molecule's properties, such as its volatility or reactivity.

Trimethylsilylamine is prepared by reacting hexamethyldisilazane with ammonia. It is sensitive to moisture and will hydrolyze to form hexamethyldisiloxane and ammonia. Due to its reactivity, it is typically handled under an inert atmosphere. Its primary applications lie in organic chemistry laboratories for derivatizing alcohols, amines, and carboxylic acids to make them more amenable to analysis by gas chromatography. It can also be used in the synthesis of other organosilicon compounds and as a precursor for nitrogen-containing silicon materials.