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Azoxybenzene

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Azoxybenzene
Names
Other names
Fenazox, diphenyldiazene Oxide
Identifiers
ECHA InfoCard 100.007.094 Edit this at Wikidata
UNII
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).

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]

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 + H2O

References

  1. ^ a b "Azoxybenzene". Organic Syntheses. 11: 16. 1931. doi:10.15227/orgsyn.011.0016. {{cite journal}}: Unknown parameter |authors= ignored (help)
  2. ^ "trans-Diphenyldiazene Oxide". Acta Crystallographica Section E. 63 (8): o3639. 2007. doi:10.1107/S1600536807035787. {{cite journal}}: Unknown parameter |authors= ignored (help)