Trimethylsilyl azide is a chemical compound

Chemical compound

A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

 used as a reagent in organic chemistry

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

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Preparation

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

Trimethylsilyl chloride

Trimethylsilyl chloride, also known as chlorotrimethylsilane is a silyl halide, with a variety of different uses in chemistry. It has the formula 3SiCl, and under standard conditions it is a colourless liquid, which is stable in the absence of water...

 and sodium azide

Sodium azide

Sodium azide is the inorganic compound with the formula NaN3. This colourless azide salt is the gas-forming component in many car airbag systems. It is used for the preparation of other azide compounds. It is an ionic substance and is highly soluble in water. It is extremely...

:

TMSCl + NaN₃ → TMSN₃ + NaCl (TMS = (CH₃)₃Si)

Applications

It is considered a safer replacement for hydrazoic acid

Hydrazoic acid

Hydrazoic acid, also known as hydrogen azide or azoimide, is a colorless, volatile, and extremely explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, having chemical formula HN3. It was first isolated in 1890 by Theodor Curtius...

 in many reactions. It will however over time hydrolyze

Hydrolysis

Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

 to hydrogen azide and therefore it must be stored free of moisture It has been used in the Oseltamivir total synthesis

Oseltamivir total synthesis

Oseltamivir total synthesis concerns the total synthesis of the antiinfluenza drug oseltamivir marketed by Hoffmann-La Roche under the trade name Tamiflu. Its commercial production starts from the biomolecule shikimic acid harvested from Chinese star anise with a limited worldwide supply...

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Safety

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids.