Trimethylsilyl azide

Trimethylsilyl azide
Skeletal formula of Trimethylsilyl azide
Ball-and-stick model of the trimethylsilyl azide molecule
Names
IUPAC name
Azido(trimethyl)silane
Identifiers
4648-54-8 YesY
3D model (Jmol) Interactive image
1903730
ChemSpider 70747 YesY
ECHA InfoCard 100.022.798
EC Number 225-078-5
PubChem 78378
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
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., gasoline) Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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

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

  1. L. Birkofer and P. Wegner (1988). "Trimethylsilyl azide". Org. Synth.; Coll. Vol., 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.
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