Trimethylsilyl azide
Trimethylsilyl azide is the organosilicon compound with the formula. 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:Reactions
The compound hydrolyzes to hydrazoic acid:The compound adds to ketones and aldehydes to give the siloxy azides and subsequently tetrazoles:
It ring-opens epoxides to give azido alcohols.
It has been used in the Oseltamivir total synthesis.