Trimethylsilyl azide

Trimethylsilyl azide is the organosilicon compound with the formula (CH3)3SiN3. A colorless liquid, it is a reagent in organic chemistry, serving as the equivalent of hydrazoic acid.

Preparation
Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:
 * (CH3)3Si\sCl + NaN3 → (CH3)3Si\sN3 + NaCl

Reactions
The compound hydrolyzes to hydrazoic acid:
 * (CH3)3SiN3 + H2O → (CH3)3SiOH + HN3

The compound adds to ketones and aldehydes to give the siloxy azides and subsequently tetrazoles:
 * (CH3)3SiN3 + R2CO → R2C(N3)OSi(CH3)3

It ring-opens epoxides to give azido alcohols.

It has been used in the Oseltamivir total synthesis.

Safety
Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids. Azides are often explosive, as illustrated by their use in air bags.