''N''-Phenylhydroxylamine is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

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

Preparation

This compound can be prepared by the reduction of

nitrobenzene Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5 NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced ...

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 increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

Reactions

Phenylhydroxylamine is unstable to heating, and in the presence of strong acids easily rearranges to

4-aminophenol 4-Aminophenol (or ''para''-aminophenol or ''p''-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal. ...

via the Bamberger rearrangement. 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 ...

. Like other hydroxylamines it will react with

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

s to form nitrones, illustrative is the condensation with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipolar compound: :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. This conjugate base is abbreviated as CU−. It once was a common reagent for the complexation of metal ions, being of interest i ...

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

References

{{reflist Hydroxylamines