Phenyl azide

Phenyl azide
Skeletal formula	Ball-and-stick model
Names
	Preferred IUPAC name Azidobenzene[1]
	Other names Phenyl azide[1]
Identifiers
CAS Number	622-37-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	62529 ;
ECHA InfoCard	100.009.756
EC Number	210-730-3;
MeSH	C014747
PubChem CID	69319;
UNII	2G0EH7N6YB ;
CompTox Dashboard (EPA)	DTXSID30878870 ;
	InChI InChI=1S/C6H5N3/c7-9-8-6-4-2-1-3-5-6/h1-5H Key: CTRLRINCMYICJO-UHFFFAOYSA-N ; InChI=1/C6H5N3/c7-9-8-6-4-2-1-3-5-6/h1-5H Key: CTRLRINCMYICJO-UHFFFAOYAH;
	SMILES [N-]=[N+]=NC1=CC=CC=C1;
Properties
Chemical formula	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
Solubility in water	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).
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	Infobox references

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°.

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.

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References

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.
R. O. Lindsay and C. F. H. Allen (1955). "Phenyl azide". Organic Syntheses.; Collective Volume, 3, p. 710
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.
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.

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[iupac2013-1] 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.

[OrgSynth-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.