923. Azoxybenzene

Nomenclature

CAS number: 495-48-7
Diphenyldiazene 1-oxide; azoxybenzide.
C12H10N2O; mol wt 198.22.
C 72.71%, H 5.08%, N 14.13%, O 8.07%.

Description and references

Prepd by reduction of nitrobenzene with sodium arsenite: Bigelow, Palmer, Org. Synth. coll. vol. II, 57 (1943); also by treatment of nitrobenzene with glucose in alkaline medium: Opolonick, Ind. Eng. Chem. 27, 1045 (1935). Industrial prepn by heating nitrobenzene with molasses and NaOH in high flash naphtha: DE 228722. Also prepd by catalytic reduction of nitrobenzene: Busch, Schulz, Ber. 62, 1458 (1929). By peracetic acid oxidation of azobenzene: D'Ans, Kneip, Ber. 48, 1145 (1915); cf. Greenspan, Ind. Eng. Chem. 39, 847 (1947). Prepn of cis- and trans-forms by perbenzoic acid oxidation of azobenzene: G. M. Badger et al., J. Chem. Soc. 1953, 2143.

Chemical structure

Derivative

trans-Form.

Nomenclature

CAS number: 20972-43-4

Properties

Pale yellow orthorhombic needles. d426 1.1590. d450 1.1373. mp 36°. Slightly volatile with steam; easily volatile in superheated steam at 140-150°. Absorption spectrum: Müller, Ann. 493, 166 (1932). Insol in water. Sol in alcohol, ether. 100 parts of abs alc satd at 16° contain 17.5 parts (w/w) azoxybenzene. At 15° 100 g ligroin dissolves 43.5 g azoxybenzene.

Derivative

cis-Form.

Nomenclature

CAS number: 21650-65-7

Properties

mp 87°.

Use

In organic syntheses.