Phenylhydroxylamine

Names

IUPAC name

N-phenylhydroxylamine

Other names

beta-henylhydroxylamine; N-hydroxyaniline; phenylhydroxylamine; N-hydroxybenzeneamine; hydroxylaminobenzene

Identifiers

CAS Number

100-65-2^Y

3D model (Jmol)

Interactive image

ChEBI

CHEBI:28902^N

ChemSpider

7237^N

209-711-2

C02720^N

PubChem CID

7518

UNII

282MU82Z9A^N

InChI

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

SMILES

ONC1=CC=CC=C1

Properties

Chemical formula

C₆H₇NO

Molar mass

109.1274 g/mol

Appearance

yellow needles

Melting point

80 to 81 °C (176 to 178 °F; 353 to 354 K)

Magnetic susceptibility (χ)

-68.2·10⁻⁶ cm³/mol

Related compounds

hydroxylamine, nitrosobenzene

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox 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.

This compound can be prepared by the reduction of nitrobenzene with zinc in the presence of NH₄Cl followed by crystallization as yellowish needles from salt-saturated water. The product can be purified from contaminating NaCl by extraction into benzene followed by precipitation with petroleum ether.

Alternatively, it can be prepared by transfer hydrogenation of nitrobenzene using hydrazine as an H₂ source over a rhodium catalyst.

Phenylhydroxylamine is unstable to heating, and in the presence of strong acids easily rearranges to 4-aminophenol. Oxidation of phenylhydroxylamine with dichromate is a useful method of preparation of nitrosobenzene.

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

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