Phenylhydroxylamine is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula C₆H₅NHOH. It is an intermediate in the redox-related pair C₆H₅NH₂ and C₆H₅NO. Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or ''O''-phenylhydroxylamine.

Preparation

This compound can be prepared by the reduction of nitrobenzene with zinc in the presence of NH₄Cl. Alternatively, it can be prepared by transfer hydrogenation of nitrobenzene using hydrazine as an H₂ source over a rhodium

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

Reactions

Phenylhydroxylamine is unstable to heating, and in the presence of strong acids easily rearranges to 4-aminophenol via the

Bamberger rearrangement The Bamberger rearrangement is the chemical reaction of phenylhydroxylamines with strong aqueous acid, which will rearrange to give 4-aminophenols. It is named for the German chemist Eugen Bamberger (1857–1932). The starting phenylhydroxylam ...

. Oxidation of phenylhydroxylamine with dichromate gives

nitrosobenzene Nitrosobenzene is the organic compound with the chemical formula, formula C6H5NO. It is one of the prototypical organic nitroso compounds. Characteristic of its functional group, it is a dark green species that exists in equilibrium with its pale ...

. The compound condenses with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipole: C₆H₅NHOH + C₆H₅CHO → C₆H₅N(O)=CHC₆H₅ + H₂O Phenylhydroxylamine is attacked by NO⁺ sources to give

cupferron Cupferron is jargon for the ammonium salt of the conjugate base derived from ''N''-nitroso-N-phenylhydroxylamine. It once was a common reagent for the complexation of metal ions, being of interest in the area of qualitative inorganic analysis. Its ...

: :C₆H₅NHOH + C₄H₉ONO + NH₃ → NH₄ ₆H₅N(O)NO+ C₄H₉OH

References

{{reflist Hydroxylamines