Bis(trimethylsilyl)acetamide


Bisacetamide is an organosilicon compound with the formula Me3SiNCMe. It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with compounds, including solvents and moisture, containing OH and NH functional groups. It is used in analytical chemistry for the derivatisation of compounds in analysis to increase their volatility, e.g. for gas chromatography. It is also used to introduce the trimethylsilyl protecting group in organic synthesis. A related reagent is N,O-bistrifluoroacetamide.

Synthesis and reactions

BSA is prepared by treating acetamide with trimethylsilyl chloride in the presence of a base:
The reaction of BSA with alcohols gives the corresponding trimethylsilyl ether, together with N-acetamide as a byproduct: