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]]