Trimethylsilyl azide ((CH
3)
3SiN
3) is a
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one ele ...
used as 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 materials, i.e., matter in its various forms that contain carbon atoms.Clay ...
.
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 (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. I ...
and
sodium azide:
: TMSCl + NaN
3 → TMSN
3 + NaCl (TMS = (CH
3)
3Si)
Applications
It is considered a safer alternative to
hydrazoic acid
Hydrazoic acid, also known as hydrogen azide 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 at room tem ...
in many reactions; however, over time it will
hydrolyze
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysis ...
to
hydrazoic acid
Hydrazoic acid, also known as hydrogen azide 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 at room tem ...
, and therefore 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. In 2014, a graduate student at the University of Minnesota was injured in an explosion that occurred in the synthesis of a large batch of trimethylsilyl azide.
[http://cenblog.org/the-safety-zone/2014/07/more-details-on-the-university-of-minnesota-explosion-and-response/]
References
{{Reflist
Azido compounds
Reagents for organic chemistry
Trimethylsilyl compounds