Phenylhydroxylamine
4417228
183986586
2008-01-13T05:22:16Z
Chem-awb
4806773
chemicals pages cleanup per [[User:Beetstra/Chemicals]] using [[Project:AutoWikiBrowser|AWB]]
{{Chembox new
| Name = Phenylhydroxylamine
| ImageFile = Phenylhydroxylamine.png
<!-- | ImageSize = 100px -->
| ImageName = Phenylhydroxylamine
| IUPACName = N-phenylhydroxylamine
| OtherNames = beta-phenylhydroxylamine,<br />
N-hydroxyaniline<br /> phenylhydroxylamine<br /> N-hydroxybenzeneamine<br /> hydroxylaminobenzene
| Section1 = {{Chembox Identifiers
| SMILES = ONC1=CC=CC=C1
| RTECS =
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>7</sub>NO
| MolarMass = 109.1274 g/mol
| Appearance = yellow needles
| Density = ? g/cm<sup>3</sup>, ?
| Solubility =
| MeltingPt = 80-81 °C
| BoilingPt =
| pKa =
}}
| Section3 = {{Chembox Structure
| MolShape =
| CrystalStruct =
| Dipole =
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| MainHazards =
| FlashPt =
| RPhrases =
| SPhrases =
}}
| Section8 = {{Chembox Related
| OtherCpds = [[hydroxylamine]], [[nitrosobenzene]]
}}
}}
'''Phenylhydroxylamine''' is the [[organic compound]] with the [[chemical formula|formula]] C<sub>6</sub>H<sub>5</sub>NHOH. It is an intermediate in the redox-related pair [[aniline|C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub>]] and [[nitrosobenzene|C<sub>6</sub>H<sub>5</sub>NO]]. Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or ''O''-phenylhydroxylamine, is C<sub>6</sub>H<sub>5</sub>ONH<sub>2</sub>.
==Preparation and derivatives==
This compound can be prepared by the reduction of [[nitrobenzene|C<sub>6</sub>H<sub>5</sub>NO<sub>2</sub>]] with zinc in the presence of NH<sub>4</sub>Cl followed by crystallization as yellowish needles from salt-saturated water.<ref>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).</ref><ref>{{OrgSynth | author = O. Kamm | title = Phenylhydroxylamine | collvol = 1 | collvolpages = 445| year = 1941 | prep = CV1P0445}}</ref> Alternatively, it can be prepared by transfer hydrogenation of C<sub>6</sub>H<sub>5</sub>NO<sub>2</sub> using hydrazine as an H<sub>2</sub> source over a rhodium catalyst.<ref>{{OrgSynth | author = P. W. Oxley, B. M. Adger, M. J. Sasse, and M. A. Forth | title = N-Acetyl-N-Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon | collvol = 16 | collvolpages = 16| year = 1993 | prep = CV8P0016}}</ref> The product can be purified from contaminating NaCl by extraction into benzene followed by precipitation with petroleum ether. C<sub>6</sub>H<sub>5</sub>NHOH is unstable to heating.
The compound condenses with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipole:<ref>{{OrgSynth | author = I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl | title = 2,3,5-Triphenylisoxazolidine | collvol = 5 | collvolpages = 1124| year = 1973 | prep = CV5P1124}}</ref>
::C<sub>6</sub>H<sub>5</sub>NHOH + C<sub>6</sub>H<sub>5</sub>CHO → C<sub>6</sub>H<sub>5</sub>N(O)=CHC<sub>6</sub>H<sub>5</sub> + H<sub>2</sub>O
==References==
{{reflist}}
[[Category:Aromatic compounds]]
[[Category:Nitrogen compounds]]
{{aromatic-stub}}
[[ca:Template:Chembox]]
[[es:Plantilla:Chembox]]
[[fr:Modèle:Chimiebox général]]