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Phenylhydroxylamine
Skeletal formula of phenylhydroxylamine
Ball-and-stick model of the phenylhydroxylamine molecule
Names
Preferred IUPAC name
N-Hydroxyaniline
Other names
beta-phenylhydroxylamine; phenylhydroxylamine; N-hydroxybenzeneamine; hydroxylaminobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.614 Edit this at Wikidata
EC Number
  • 209-711-2
KEGG
UNII
  • InChI=1S/C6H7NO/c8-7-6-4-2-1-3-5-6/h1-5,7-8H ☒N
    Key: CKRZKMFTZCFYGB-UHFFFAOYSA-N ☒N
  • InChI=1/C6H7NO/c8-7-6-4-2-1-3-5-6/h1-5,7-8H
    Key: CKRZKMFTZCFYGB-UHFFFAOYAK
  • ONC1=CC=CC=C1
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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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.

Preparation[edit]

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[edit]

Cupferron (N-nitroso-N-phenylhydroxylamine), a reagent for qualitative inorganic analysis, is prepared from phenylhydroxylamine.

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.

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]

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

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

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

References[edit]

  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl (1966). "2,3,5-Triphenylisoxazolidine". Organic Syntheses. 46: 127. doi:10.15227/orgsyn.046.0127.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ C. S. Marvel (1925). "Cupferron". Organic Syntheses. 4: 19. doi:10.15227/orgsyn.004.0019.
source: https://en.wikipedia.org/wiki/Phenylhydroxylamine

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