Trimethylsilyl azide
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Names | |||
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IUPAC name
Azido(trimethyl)silane | |||
Identifiers | |||
4648-54-8 | |||
3D model (Jmol) | Interactive image | ||
1903730 | |||
ChemSpider | 70747 | ||
ECHA InfoCard | 100.022.798 | ||
EC Number | 225-078-5 | ||
PubChem | 78378 | ||
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Properties | |||
C3H9N3Si | |||
Molar mass | 115.21 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 | R11, R23, R24, R25, R29, R50, R51, R52, R53 | ||
S-phrases | S16,S29,S36, S37,S45,S57,S8, | ||
NFPA 704 | |||
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). | |||
verify (what is ?) | |||
Infobox references | |||
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 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.
References
- ↑ L. Birkofer and P. Wegner (1988). "Trimethylsilyl azide". Org. Synth.; Coll. Vol., 6, p. 1030
- ↑ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144. doi:10.1055/s-2007-984895.
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