My watch list  

Phenyl azide

Phenyl azide
Systematic name Phenyl azide
Other names Azidobenzene
Molecular formula C6H5N3
Molar mass 119.14 g/mol
Appearance pale yellow, oily
CAS number [622-37-7]
Density and phase  ? g/cm3, liquid
Solubility in water not appreciable
Other solvents common organic solvents
Melting point  ? °C (? K)
Boiling point 49–50 °C at 5 mm Hg
Viscosity  ? cP at ? °C
MSDS External MSDS
Main hazards explosive
NFPA 704
Flash point  ? °C
R/S statement R: ?
S: ?
RTECS number  ?
Supplementary data page
Structure and
n, εr, etc.
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related compounds PhNHNH2
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Phenylazide is an organic compound with the formula C6H5N3. It is one of the prototypical organic azides. It has a pungent odor.

It is prepared by the diazotization of phenylhydrazine with nitrous acid:[1]

C6H5NHNH2 + HNO2 → C6H5N3 + 2 H2O

The structure consists of a linear N=N=N substituent bound to a phenyl group. The C-N=N angle is approximately 120°.


Chemical reactions

C6H5N3 is used to make heterocycles via cycloaddition to alkenes and especially alkynes, particularly those bearing electronegative substituents. It reacts with triphenylphosphine to give the Staudinger reagent C6H5NP(C6H5)3. Thermolysis induces loss of N2 to give the highly reactive phenylnitrene C6H5N.[2]

Other fundamental phenyl-N molecules

Related phenyl-N building blocks include C6H5NH2, C6H5NO, C6H5NO2, C6H5NHOH, C6H5NHNH2, and C6H5N2+.


A protective blast shield is needed during purification and handling. Distillation temperatures should be as low a possible. Organic Syntheses recommends 5mm Hg to give a boiling point of “66–68 °C/21 mm. with a bath temperature of 70–75 °C.” The pure substance may be stored in the dark, cold, and even then the shelf-life is only weeks.


  1. ^ R. O. Lindsay; C. F. H. Allen. "Phenyl Azide" Organic Syntheses, Collected Volume 3, page 710.
  2. ^ W. H. Pearson, P. S. Ramamoorthyin “Phenyl Azide” Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phenyl_azide". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE