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]