Phenyl azide

Phenyl azide

Skeletal formula Ball-and-stick model
Names
Preferred IUPAC name Azidobenzene
Other names Phenyl azide
Identifiers
CAS Number	622-37-7 Y
3D model (JSmol)	Interactive image
ChemSpider	62529 N
ECHA InfoCard	100.009.756
EC Number	210-730-3
MeSH	C014747
PubChem CID	69319
UNII	2G0EH7N6YB Y
CompTox Dashboard (EPA)	DTXSID30878870
InChI InChI=1S/C6H5N3/c7-9-8-6-4-2-1-3-5-6/h1-5H N Key: CTRLRINCMYICJO-UHFFFAOYSA-N 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
Occupational safety and health (OHS/OSH):
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

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:

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):

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.

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, 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." The pure substance may be stored in the dark, cold, and even then the shelf-life is only weeks.