Title: Azoxybenzene
CAS Registry Number: 495-48-7
CAS Name: Diphenyldiazene 1-oxide
Synonyms: azoxybenzide
Molecular Formula: C12H10N2O
Molecular Weight: 198.22
Percent Composition: C 72.71%, H 5.08%, N 14.13%, O 8.07%
Literature 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.
Derivative Type: trans-Form
CAS Registry 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.
Melting point: mp 36°
Density: d426 1.1590; d450 1.1373
Derivative Type: cis-Form
CAS Registry Number: 21650-65-7
Properties: mp 87°.
Melting point: mp 87°
Use: In organic syntheses.
