[13475-12-6] · C5H13NOSi · N-Trimethylsilylacetamide · (MW 131.28)
Alternate Name: MSA.
Physical Data: mp 46-49 °C; bp 84 °C/18 mmHg; fp 57 °C.
Form Supplied in: moist white crystals.
Handling, Storage, and Precautions: handle and store under nitrogen; combustible and easily hydrolyzed.
N-Trimethylsilylacetamide has poor silylation potential1 and although not as frequently used as N,O-Bis(trimethylsilyl)acetamide (BSA) as a silylating agent, this reagent has found a number of uses. N-Trimethylsilylacetamide has been used to silylate alcohols,2 the hydroxy groups of sugars,3 carboxylic acids,4 amino groups,5 and the oxygen of phosphate esters (eqs 1 and 2).6
The dianion of N-trimethylsilylacetamide can be used as a soluble alternate to the insoluble acetamide dianion. The dianion can be alkylated or acylated at carbon (eqs 3-5).7
In an unusual reaction, N-trimethylsilylacetamide in the presence of Trifluoromethanesulfonic Anhydride can be used to N-glycosylate the anomeric positions of sugars (eq 6).8
Janet Wisniewski Grissom
University of Utah, Salt Lake City, UT, USA