N-Phenylhydroxylamine

N-Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or O-phenylhydroxylamine.

This compound can be prepared by the reduction of nitrobenzene with zinc in the presence of NH4Cl.

[1][2] Alternatively, it can be prepared by transfer hydrogenation of nitrobenzene using hydrazine as an H2 source over a rhodium catalyst.

Oxidation of phenylhydroxylamine with dichromate gives nitrosobenzene.

Like other hydroxylamines it will react with aldehydes to form nitrones, illustrative is the condensation with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipolar compound:[4] Phenylhydroxylamine is attacked by NO+ sources to give cupferron:[5]

Skeletal formula of phenylhydroxylamine
Ball-and-stick model of the phenylhydroxylamine molecule
Cupferron ( N -nitroso-N-phenylhydroxylamine), a reagent for qualitative inorganic analysis , is prepared from phenylhydroxylamine.