Phenyl azide

Phenyl azide

Chembox new
Name = Phenyl azide
ImageFile = Phenyl-azide-A-2D-skeletal.png ImageName = Phenyl azide
IUPACName = Phenyl azide
OtherNames = Azidobenzene
Section1 = Chembox Identifiers
SMILES =
CASNo = 622-37-7
RTECS =

Section2 = Chembox Properties
Formula = C6H5N3
MolarMass = 119.14 g/mol
Appearance = pale yellow, oily
Density = ? g/cm3, liquid
Solubility = not appreciable
MeltingPt = (? K)
BoilingPt = 49–50 °C at 5 mm Hg
Viscosity =

Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = explosive
FlashPt =
RPhrases =
SPhrases =

Section8 = Chembox Related
Function = compounds
OtherFunctn = PhNHNH2
PhNO,
PhN2+

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: [R. O. Lindsay; C. F. H. Allen. "Phenyl Azide" Organic Syntheses, Collected Volume 3, page 710.] :C6H5NHNH2 + HNO2 → C6H5N3 + 2 H2OThe 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. [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.]

Other fundamental phenyl-N molecules

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

afety

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.

References


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