Nitrosobenzene
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| Nitrosobenzene | |
|---|---|
| |
| General | |
| Systematic name | Nitrosobenzene |
| Other names | ? |
| Molecular formula | C6H5NO |
| SMILES | O=Nc1ccccc1 |
| Molar mass | 107.11 g/mol |
| Appearance | colourless solid |
| CAS number | [586-96-9] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | low |
| Other solvents | sol. in organic solvents |
| Melting point | 65-69 °C |
| Boiling point | 59 °C, 18 mm Hg |
| Acidity (pKa) | ? |
| Viscosity | ? cP at ? °C |
| Structure | |
| Molecular shape | N is sp2 |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | toxic |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: 20/21-25 S: 26-36/37-45 |
| RTECS number | DA6497525 |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related Nitroso compounds | ? |
| Related compounds | Nitrobenzene Aniline |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Nitrosobenzene is the organic compound C6H5NO. The compound can be viewed as hybrid of singlet O2 and azobenzene. This diamagnetic species exists in equilibrium with its dimer.
Preparation
C6H5NO was first reported by Adolf Baeyer in 1874,[1] who prepared it by the reaction of diphenylmercury and nitrosylbromide, "Bringt man eine Loesung von NOBr in Benzol in eine Loesung von Quecksilberphenyl in Benzol …"
- [C6H5]2Hg + BrNO → C6H5NO + C6H5HgBr
The modern synthesis entails reduction of nitrobenzene to phenylhydroxylamine, C6H5NHOH, which is then oxidized by Na2Cr2O7.[1] C6H5NO was also prepared by Caro via oxidation of aniline using peroxymonosulfuric acid, Caro's acid.[1] It is usually purified by steam distillation, where it comes over as a green liquid that solidifes to a colorless solid.
Characteristic reactions
The monomer undergoes Diels-Alder reactions with dienes.[1] Most characteristically nitrosobenzene condenses with "active" methylene and amine groups, e.g. of malonic esters. Condensation with anilines affords azobenzene derivatives (Mills reaction) and condensation with benzylcyanide PhCH2CN the imine PhC(CN)=NPh (The Ehrlich-Sachs Reaction, 1899) [1] [1]
Reduction of PhNO produces C6H5NH2.
See also
References
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Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
