Trimethylsilyl azide

Trimethylsilyl azide

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 [Organic Syntheses, Coll. Vol. 6, p.1030 (1988); Vol. 50, p.107 (1970). [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p1030 Link] .] 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 ["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] . For an example of its use: see Oseltamivir total synthesis.

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