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N-Phenylhydroxylamine

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N-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 InfoCard100.002.614Edit 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 mass109.1274 g/mol
Appearanceyellow needles
Melting point80 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

N-Phenylhydroxylamine is theorganic compound with theformula C6H5NHOH. It is an intermediate in the redox-related pairC6H5NH2 andC6H5NO.N-Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine orO-phenylhydroxylamine.

Preparation

[edit]

This compound can be prepared by the reduction ofnitrobenzene 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 rhodiumcatalyst.[3]

Reactions

[edit]
Cupferron (N-nitroso-N-phenylhydroxylamine), a reagent forqualitative inorganic analysis, is prepared from phenylhydroxylamine.

Phenylhydroxylamine is unstable to heating, and in the presence of strong acids easily rearranges to4-aminophenol via theBamberger rearrangement. Oxidation of phenylhydroxylamine withdichromate givesnitrosobenzene.

Like other hydroxylamines it will react withaldehydes to formnitrones, illustrative is the condensation with benzaldehyde to form diphenylnitrone, a well-known1,3-dipolar compound:[4]

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

Phenylhydroxylamine is attacked by NO+ sources to givecupferron:[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.
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