Azoxybenzene is organic compound with the formula C6H5N(O)NC6H5. It is a yellow, low-melting solid.[1] The molecule has a planar C2N2O core. The N-N and N-O bond lengths are nearly the same at 1.23 Å.[2]
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Other names Fenazox, diphenyldiazene Oxide | |
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Properties | |
C12H10N2O | |
Molar mass | 198.225 g·mol−1 |
Appearance | yellow solid |
Density | 1.318 g/cm3 |
Melting point | 35.5–36.5 °C (95.9–97.7 °F; 308.6–309.6 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Preparation
It can be prepared by partial reduction of nitrobenzene. This reaction is proposed to proceed via the intermediacy of phenylhydroxylamine and nitrosobenzene:[1]
- PhNHOH + PhNO → PhN(O)NPh + H 2O
Another option is the oxidation of aniline by hydrogen peroxide, in acetonitrile at 50 ºC. In this reaction, the pH should be kept around 8, to activate the hydrogen peroxide and avoid too much oxygen evolution at the same time. First, the acetonitrile is oxidized, forming an imine hydroperoxide. Then, this intermediate oxidizes the aniline to azoxybenzene. [3]
- CH 3CN + H 2O 2 → [CH 3C(OOH)=NH]
- 2 PhNH 2 + 3 [CH 3C(OOH)=NH] → PhN(O)NPh + 3 CH 3C(O)NH 2 + 2 H 2O
References
- ^ a b H. E. Bigelow, Albert Palmer (1931). "Azoxybenzene". Organic Syntheses. 11: 16. doi:10.15227/orgsyn.011.0016.CS1 maint: uses authors parameter (link)
- ^ S. P. G. Martínez, S. Bernès (2007). "trans-Diphenyldiazene Oxide". Acta Crystallographica Section E. 63 (8): o3639. doi:10.1107/S1600536807035787.CS1 maint: uses authors parameter (link)
- ^ George B. Payne, Philip H. Deming, Paul H. Williams (1961). "Reactions of Hydrogen Peroxide. VII. Alkali-Catalyzed Epoxidation and Oxidation Using a Nitrile as Co-reactant". The Journal of Organic Chemistry. 26: 659-663. doi:10.1021/jo01062a004.CS1 maint: uses authors parameter (link)