Trimethylsilyl azide

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Trimethylsilyl azide ((CH3)3SiN3) is a chemical compound used as a reagent in organic chemistry. It can be produced from trimethylsilyl chloride and sodium azide [1] It is considered a safer replacement for hydrazoic acid in many reactions. It will however over time hydrolyze to hydrogen azide and therefore it must be stored free of moisture [2]. For an example of its use: see Oseltamivir total synthesis.

[edit] References

  1. ^ Organic Syntheses, Coll. Vol. 6, p.1030 (1988); Vol. 50, p.107 (1970). Link.
  2. ^ Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis Mohammad Jafarzadeh SYNLETT 2007, No. 13, pp 2144–2145 doi:10.1055/s-2007-984895 Open access