7252. Phenothiazine

Nomenclature

CAS number: 92-84-2
10H-Phenothiazine; thiodiphenylamine; dibenzothiazine; AFI-Tiazin; Antiverm; Fentiazin; Helmetina; Lethelmin; Nemazine; Orimon; Phénégic; Phenoverm; Phenovis; Phenoxur; Reconox; Souframine; Vermitin.
C12H9NS; mol wt 199.27.
C 72.33%, H 4.55%, N 7.03%, S 16.09%.

Description and references

Prepd by fusing diphenylamine with sulfur: Bernthsen, Ber. 16, 2896 (1883); Ann. 230, 73 (1885); DE 25150 (1883), Frdl. 1, 252. Improved yields with iodine as catalyst: Knoevenagel, J. Prakt. Chem. [2] 89, 11 (1914); Mitchell, Webb, US 2415363 (1947 to Koppers). Purification: Vierling, US 2887482 (1959); Rigby, US 3000887 (1961 to Shell Oil). Crystal structure: J. D. Bell et al., Chem. Commun. 1968, 1656.

Chemical structure

Properties

Yellow, rhombic leaflets or diamond-shaped plates from toluene or butanol, mp 185.1°. Sublimes at 130° at 1 mm. bp760 371°; bp40 290°. Freely sol in benzene; sol in ether, in hot acetic acid; slightly sol in alcohol and in mineral oils. Practically insol in petr ether, chloroform, water. Readily oxidized by sunlight or when in presence of a finely divided inert carrier, acquiring a greenish-brown tint. This can be prevented by the admixture of 0.3-1.0% methenamine.

Caution

Potential symptoms of overexposure are itching, irritation and reddening skin; hepatitis, hemolytic anemia, abdominal cramps, tachycardia; kidney damage; skin sensitization and photophobia. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 248.

Use

Insecticide; manuf pharmaceuticals.

Therapeutic Category (Veterinary)

Anthelmintic.