Phenylhydroxylamine
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| Phenylhydroxylamine | |
|---|---|
 |
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| General | |
| Systematic name | N-phenylhydroxylamine |
| Other names | beta-phenylhydroxylamine, N-hydroxyaniline |
| Molecular formula | C6H7NO |
| SMILES | ONC1=CC=CC=C1 |
| Molar mass | 109.1274 g/mol |
| Appearance | yellow needles |
| CAS registry number | [100-65-2] [1] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | ? g/100 ml (? °C) |
| Melting point | 80-81 °C |
| Boiling point | ? °C (? K) |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Chiral rotation [α]D | ?° |
| Viscosity | ? cP at ? °C |
| Structure | |
| Molecular shape | ? |
| Coordination geometry |
? |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | ? |
| Other cations | ? |
| Related ? | ? |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Phenylhydroxylamine, sometimes called β-phenylhydroxylamine or N-phenylhydroxylamine, is 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, is C6H5ONH2.
[edit] Preparation and derivatives
This compound can be prepared by the reduction of C6H5NO2 with zinc in the presence of NH4Cl followed by crystallization as yellowish needles from salt-saturated water. Alternatively, it can be prepared by transfer hydrogenation of C6H5NO2 using hydrazine as an H2 source over a rhodium catalyst. The product can be purified from contaminating NaCl by extraction into benzene followed by precipitation with petroleum ether. C6H5NHOH is unstable to heating.
The compound condenses with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipole:
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- C6H5NHOH + C6H5CHO → C6H5N(O)=CHC6H5 + H2O
[edit] References
- 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).
- O. Kamm, "É¿-Phenylhydroxylamine" Organic Syntheses Collective Volume 1, page 445 (1941).
- P. W. Oxley, B. M. Adger, M. J. Sasse, and M. A. Forth, N-Acetyl-N-Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon” Organic Syntheses, Coll. Vol. 8, p.16; Vol. 67, p.187.
- I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl, “2,3,5-Triphenylisoxazolidine” Organic Syntheses, Coll. Vol. 5, p.1124 (1973); Vol. 46, p.127 (1966). (describing the condensation of PhNHOH with PhCHO). I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl “2-Phenyl-3-n-propylisoxazolidine-4,5-cis-dicarboxylic Acid N-Phenylimide” Organic Syntheses, Coll. Vol. 5, p.957 (1973); Vol. 46, p.96 (1966) (condensation of PrCHO and PhNHOH).
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