Trimethylsilyl azide
Appearance
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Names | |||
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Preferred IUPAC name
Azidotri(methyl)silane | |||
Identifiers | |||
3D model (JSmol)
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1903730 | |||
ChemSpider | |||
ECHA InfoCard | 100.022.798 | ||
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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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: | |||
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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) | |||
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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Trimethylsilyl azide ((CH3)3SiN3) is a chemical compound used as a reagent in organic chemistry.
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
- ^ L. Birkofer and P. Wegner (1988). "Trimethylsilyl azide". Organic Syntheses; Collected Volumes, vol. 6, p. 1030.
- ^ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144–2145. doi:10.1055/s-2007-984895.
- ^ http://cenblog.org/the-safety-zone/2014/07/more-details-on-the-university-of-minnesota-explosion-and-response/