|Jmol-3D images||Image 1|
|Molar mass||107.11 g mol−1|
|Melting point||65 to 69 °C (149 to 156 °F; 338 to 342 K)|
|Boiling point||59 °C (138 °F; 332 K) (at 18 mmHg)|
|Solubility in water||Low|
|Solubility in other solvents||Sol. in organic solvents|
|Molecular shape||N is sp2|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
- (C6H5)2Hg + BrNO → C6H5NO + C6H5HgBr
Nitrosobenzene can also be prepared by oxidation of aniline using peroxymonosulfuric acid (Caro's acid). It is usually purified by steam distillation, where it comes over as a green liquid that solidifes to a colorless solid.
Nitrosobenzene undergoes Diels–Alder reactions with dienes. Condensation with anilines affords azobenzene derivatives in a reaction known as the Mills reaction. Reduction of nitrosobenzene produces aniline.
Most characteristically, nitrosobenzene condenses with active methylene groups, such as those of malonic esters and benzyl cyanide. For example, condensation with benzylcyanide (PhCH2CN) gives the imine (PhC(CN)=NPh) in a reaction known as the Ehrlich-Sachs Reaction:
- Ph–CH2-CN + Ph–NO → Ph–CH(CN)–N(OH)–Ph (oxyamination adduct) → PhC(CN)=N–Ph
Sometimes condensation with active methylene compounds could give products of O-nitroso-aldol reaction:
- R–CH2-CHO + Ph–NO → R–CH(CHO)–O–NHPh (aminoxylation adduct)
- Baeyer, A. (1874). "Nitrosobenzol und Nitrosonaphtalin". Chemische Berichte 7: 1638–1640.
- G. H. Coleman, C. M. McCloskey, F. A. Stuart (1955), "Nitrosobenzene", Org. Synth.; Coll. Vol. 3: 668
- H. Caro (1898). Z. angew. Chem. 11: 845ff.
- H. Yamamoto, N. Momiyama "Rich Chemistry of Nitroso Compounds" Chemical Communications 2005, pp.3514–25.
- H. D. Anspon (1955), "p-Phenylazobenzoic Acid", Org. Synth.; Coll. Vol. 3: 711
- H. Feuer. S. Patai, ed. The Chemistry of the Nitro and Nitroso Groups Part 1 (New York: Wiley). pp. 278–283.
- "Asymmetric O− and N− Nitroso Aldol Reaction – an efficient access to a-oxy and a-amino carbonyl compound".