2257. Chrysoidine

Nomenclature

CAS number: 532-82-1
4-(Phenylazo)-1,3-benzenediamine monohydrochloride; 4-phenylazo-m-phenylenediamine hydrochloride; 2,4-diaminoazobenzene hydrochloride; chrysoidine orange; chrysoidine Y; C.I. 11270; C.I. Basic Orange 2.
C12H13ClN4; mol wt 248.71.
C 57.95%, H 5.27%, Cl 14.25%, N 22.53%.

Description and references

Prepn: Hofmann, Ber. 10, 213 (1877); Maximoff, US 2053095 (1935 to Azodal Co.). Prepn of salt: DE 562392 (1933 to Chem.-Pharm. Fabrik Hubold & Bartsch). See also Colour Index vol. 4 (3rd ed., 1971) p 4019; H. J. Conn's Biological Stains, R. D. Lillie, Ed. (Williams & Wilkins, Baltimore, 9th ed., 1977) p 87.

Chemical structure

Properties

Reddish-brown crystalline powder, mp 118-118.5°. Solubility at 15°: water 5.5%; abs ethanol 4.75%; cellosolve 6.0%; anhydr ethylene glycol 9.5%; xylene 0.005%; slightly sol in acetone. Practically insol in benzene. Gives yellow soln in concd H2SO4, orange soln in dil H2SO4 and in HNO3.

Derivative

Citrate.

Nomenclature

CAS number: 5909-04-6
4-Phenylazo-m-phenylenediamine hydrochloride citrate; 2,4-diaminoazobenzene hydrochloride citrate; Azoangin (Ursapharm); Azohel (Ursapharm).
C12H13ClN4.C6H8O7; mol wt 440.83.
C 49.04%, H 4.80%, Cl 8.04%, N 12.71%, O 25.41%.

Properties

Sol in water (up to 4%), alcohol.

Derivative

Free base.

Nomenclature

CAS number: 495-54-5
C.I. Solvent Orange 3.
C12H12N4; mol wt 212.25.
C 67.91%, H 5.70%, N 26.40%.

Use

Dyeing silk and cotton. Biological stain.

Therapeutic Category

Citrate as antiseptic.