Bis(trimethylsilyl)acetamide

Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula MeC(OSiMe3)NSiMe3 (Me = CH3).

It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with moisture and solvents containing OH and NH groups.

[1] It is also used to introduce the trimethylsilyl protecting group in organic synthesis.

[2] A related reagent is N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA).

BSA is prepared by treating acetamide with trimethylsilyl chloride in the presence of a base (Me = CH3, Et = C2H5):[2] The reaction of BSA with alcohols gives the corresponding trimethylsilyl ether, together with acetamide as a byproduct (Me = CH3):[3]

Structural formula of (E)-bis(trimethylsilyl)acetamide
Structural formula of (E)-bis(trimethylsilyl)acetamide
Ball and stick model of (E)-bis(trimethylsilyl)acetamide
Ball and stick model of (E)-bis(trimethylsilyl)acetamide