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
Preferred IUPAC name
Azidotri(methyl)silane
Identifiers
3D model (JSmol)
1903730
ChemSpider
ECHA InfoCard 100.022.798
EC Number
  • 225-078-5
  • InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 checkY
    Key: SEDZOYHHAIAQIW-UHFFFAOYSA-N checkY
  • InChI=1/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3
    Key: SEDZOYHHAIAQIW-UHFFFAOYAJ
  • [N-]=[N+]=N[Si](C)(C)C
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
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS09: Environmental hazard
Danger
H225, H301, H311, H331, H410
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P311, P312, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
4
3
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).
checkY verify (what is checkY☒N ?)
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 alternative to hydrazoic acid in many reactions; however, over time it will hydrolyze to hydrazoic acid, and therefore 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, vol. 6, p. 1030
  2. Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144–2145. 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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