Trimethylsilyl azide is the

organosilicon compound Organosilicon chemistry is the study of organometallic compounds containing carbon–silicon bonds, to which they are called organosilicon compounds. Most organosilicon compounds are similar to the ordinary organic compounds, being colourless, f ...

with the formula . A colorless liquid, it is a reagent in

organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, serving as the equivalent of

hydrazoic acid Hydrazoic acid, also known as hydrogen azide, azic acid or azoimide, This also contains a detailed description of the contemporaneous production process. is a compound with the chemical formula . It is a colorless, volatile, and explosive liquid ...

Preparation

Trimethylsilyl azide is commercially available. It may be prepared by the reaction of

trimethylsilyl chloride Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound ( silyl halide), with the formula , often abbreviated or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely u ...

and

sodium azide Sodium azide is an inorganic compound with the formula . This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is highly soluble in water and is acutely poisonou ...

: :

Reactions

The compound

hydrolyzes Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

: : 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.

Safety

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

air bag An airbag is a vehicle occupant-restraint system using a bag designed to inflate in milliseconds during a collision and then deflate afterwards. It consists of an airbag cushion, a flexible fabric bag, an inflation module, and an impact sensor. ...

References

{{Reflist Azido compounds Reagents for organic chemistry Trimethylsilyl compounds