Phenylhydroxylamine

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.

Phenylhydroxylamine
Skeletal formula of phenylhydroxylamine
Ball-and-stick model of the phenylhydroxylamine molecule
Names
IUPAC name
N-phenylhydroxylamine
Other names
beta-phenylhydroxylamine; N-hydroxyaniline; phenylhydroxylamine; N-hydroxybenzeneamine; hydroxylaminobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.614
EC Number
  • 209-711-2
KEGG
UNII
Properties
C6H7NO
Molar mass 109.1274 g/mol
Appearance yellow needles
Melting point 80 to 81 °C (176 to 178 °F; 353 to 354 K)
-68.2·10−6 cm3/mol
Related compounds
Related compounds
 hydroxylamine, nitrosobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

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.[3]

Reactions

Phenylhydroxylamine is unstable to heating, and in the presence of strong acids easily rearranges to 4-aminophenol via the Bamberger rearrangement. Oxidation of phenylhydroxylamine with dichromate gives nitrosobenzene.

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

C6H5NHOH + C6H5CHO → C6H5N(O)=CHC6H5 + H2O
Cupferron (N-nitroso-N-phenylhydroxylamine), a reagent for qualitative inorganic analysis, is prepared from phenylhydroxylamine.

Phenylhydroxylamine is attacked by NO+ sources to give cupferron:[5]

C6H5NHOH + C4H9ONO + NH3 → NH4[C6H5N(O)NO] + C4H9OH

References
  1. E. Bamberger “Ueber das Phenylhydroxylamin” Chemische Berichte, volume 27 1548-1557 (1894). E. Bamberger, "Ueber die Reduction der Nitroverbindungen" Chemische Berichte, volume 27 1347-1350 (1894) (first report).
  2. O. Kamm (1941). "Phenylhydroxylamine". Organic Syntheses. 4: 57. doi:10.15227/orgsyn.004.0057.
  3. P. W. Oxley, B. M. Adger, M. J. Sasse, M. A. Forth (1989). "N-Acetyl-N-Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon". Organic Syntheses. 67: 187. doi:10.15227/orgsyn.067.0187.CS1 maint: multiple names: authors list (link)
  4. I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl (1966). "2,3,5-Triphenylisoxazolidine". 46: 127. doi:10.15227/orgsyn.046.0127. Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
  5. C. S. Marvel (1925). "Cupferron". Organic Syntheses. 4: 19. doi:10.15227/orgsyn.004.0019.
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