Trimethylsilyl azide

From Wikipedia, the free encyclopedia
  (Redirected from Trimethylsilylazide)
Jump to: navigation, search
Trimethylsilyl azide
Trimethylsilyl azide.png
Trimethylsilyl-azide-3D-spacefill.png
Identifiers
CAS number 4648-54-8 YesY
PubChem 78378
ChemSpider 70747 YesY
EC number 225-078-5
Beilstein Reference 1903730
Jmol-3D images Image 1
Properties
Molecular formula C3H9N3Si
Molar mass 115.21 g mol−1
Appearance clear liquid, color less
Density 0.8763 g/cm3 (20 C)
Melting point -95°C
Boiling point 52-53°C at 175mmHg; 92-95°C at 760mmHg
Solubility in water 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
Flash point 6 °C (43 °F; 279 K)
Autoignition temperature > 300 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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

Preparation[edit]

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[edit]

It is considered a safer replacement for hydrazoic acid in many reactions. It will however over time hydrolyze to hydrogen azide and therefore it must be stored free of moisture [2] It has been used in the Oseltamivir total synthesis.

Safety[edit]

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids.

References[edit]

  1. ^ L. Birkofer and P. Wegner (1988), "Trimethylsilyl azide", Org. Synth. ; Coll. Vol. 6: 1030 
  2. ^ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis". Synlett 2007 (13): 2144. doi:10.1055/s-2007-984895.