Phenyl azide

Phenyl azide is an organic compound with the formula C6H5N3. It is one of the prototypical organic azides. It is a pale yellow oily liquid with a pungent odor. The structure consists of a linear azide substituent bound to a phenyl group. The C−N=N angle is approximately 120°.

Phenyl azide
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Azidobenzene[1]
Other names
Phenyl azide[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.756
EC Number
  • 210-730-3
MeSH C014747
UNII
Properties
C6H5N3
Molar mass 119.127 g·mol−1
Appearance Pale yellow, oily liquid
Boiling point 49 to 50 °C (120 to 122 °F; 322 to 323 K) at 5 mmHg
not appreciable
Hazards
Main hazards explosive
Related compounds
Related compounds
 Aniline
Nitrobenzene
Nitrosobenzene
Phenylhydrazine
Phenylhydroxylamine
Diazonium cation
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Preparation

Phenyl azide is prepared by the diazotization of phenylhydrazine with nitrous acid:[2]

C6H5NHNH2 + HNO2 → C6H5N3 + 2 H2O

Aryl iodides bearing electron-withdrawing substituents undergo metathesis with sodium azide in the presence of Cu(I), sodium ascorbate, and N,N'-dimethylethane-1,2-diamine (DMEDA):[3]

RC6H4I + NaN3 → RC6H4N3 + NaI

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 triphenylphosphine phenylimide (C6H5NP(C6H5)3). Thermolysis induces loss of N2 to give the highly reactive phenylnitrene C6H5N.[4]

Phenyl azide and its analogues undergo the azide alkyne Huisgen cycloaddition, a classic example of click chemistry. For example, phenyl azide and phenylacetylene give diphenyl triazole.

Safety

As with many other azides, phenyl azide poses a risk of explosion,[2] so a protective blast shield is recommended during purification and handling. Distillation temperatures should be as low a possible. Organic Syntheses recommends a vacuum of 5mm Hg to give a boiling point of "66–68 °C/21 mm. with a bath temperature of 70–75 °C."[2] The pure substance may be stored in the dark, cold, and even then the shelf-life is only weeks.

gollark: Seems wasteful.
gollark: With null-terminated strings, getting the length takes `O(n)` time, and it is possible to mess up very easily.
gollark: Yes, that is the superior one.
gollark: They are the LEAST cool string type.
gollark: > null-terminated strings

References
  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 66, 1119. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. R. O. Lindsay and C. F. H. Allen (1955). "Phenyl azide". Organic Syntheses.; Collective Volume, 3, p. 710
  3. Andersen, Jacob; Madsen, Ulf; Björkling, Fredrik; Liang, Xifu (2005). "Rapid Synthesis of Aryl Azides from Aryl Halides under Mild Conditions". Synlett. 2005 (14): 2209–2213. doi:10.1055/s-2005-872248. ISSN 0936-5214.
  4. 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 issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.