Trimethylsilyl azide

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

Trimethylsilyl azide
Skeletal formula of Trimethylsilyl azide
Ball-and-stick model of the trimethylsilyl azide molecule
Names
IUPAC name
Azido(trimethyl)silane
Identifiers
3D model (JSmol)
1903730
ChemSpider
ECHA InfoCard 100.022.798
EC Number
  • 225-078-5
Properties
C3H9N3Si
Molar mass 115.211 g·mol−1
Appearance clear liquid, colorless
Density 0.8763 g/cm3 (20 °C)
Melting point −95 °C (−139 °F; 178 K)
Boiling point 52 to 53 °C (126 to 127 °F; 325 to 326 K) at 175 mmHg (92 to 95 °C at 760 mmHg)
reacts to form dangerous hydrazoic acid
Hazards
R-phrases (outdated) R11, R23, R24, R25, R29, R50, R51, R52, R53
S-phrases (outdated) S16,S29,S36, S37,S45,S57,S8,
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
4
0
Flash point 6 °C (43 °F; 279 K)
> 300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:[1]

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 [2] 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.[3]

References
  1. L. Birkofer and P. Wegner (1988). "Trimethylsilyl azide". Organic Syntheses.; Collective Volume, 6, p. 1030
  2. Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144. doi:10.1055/s-2007-984895.
  3. http://cenblog.org/the-safety-zone/2014/07/more-details-on-the-university-of-minnesota-explosion-and-response/
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