Phenylhydroxylamine

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Phenylhydroxylamine
IUPAC name	N-phenylhydroxylamine
Other names	beta-phenylhydroxylamine, N-hydroxyaniline phenylhydroxylamine N-hydroxybenzeneamine hydroxylaminobenzene
Identifiers
CAS number
SMILES	ONC1=CC=CC=C1
Properties
Molecular formula	C6H7NO
Molar mass	109.1274 g/mol
Appearance	yellow needles
Density	? g/cm3, ?
Melting point	80-81 °C
Related compounds
Related compounds	hydroxylamine, nitrosobenzene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Phenylhydroxylamine is the organic compound 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, is C₆H₅ONH₂.

[edit] Preparation and derivatives

This compound can be prepared by the reduction of C₆H₅NO₂ with zinc in the presence of NH₄Cl followed by crystallization as yellowish needles from salt-saturated water.^[1][2] Alternatively, it can be prepared by transfer hydrogenation of C₆H₅NO₂ using hydrazine as an H₂ source over a rhodium catalyst.^[3] The product can be purified from contaminating NaCl by extraction into benzene followed by precipitation with petroleum ether. C₆H₅NHOH is unstable to heating.

The compound condenses with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipole:^[4]

C₆H₅NHOH + C₆H₅CHO → C₆H₅N(O)=CHC₆H₅ + H₂O

[edit] References