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Trimethylsilyl azide

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Density
  
876 kg/m³

Appearance
  
clear liquid, colorless

Melting point
  
-95 °C

Trimethylsilyl azide wwworgsynorgcontentfigurescv6p1032agif

Trimethylsilyl azide ((CH3)3SiN3) is a chemical compound used as a reagent in organic chemistry.

Contents

Preparation

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

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

Applications

It is considered a safer replacement for hydrazoic acid in many reactions. It will however over time hydrolyze to hydrazoic acid and therefore it must be stored free of moisture It has been used in the Oseltamivir total synthesis.

Safety

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

References

Trimethylsilyl azide Wikipedia