3317. Diphenylamine

Nomenclature

CAS number: 122-39-4
N-Phenylbenzeneamine.
C12H11N; mol wt 169.22.
C 85.17%, H 6.55%, N 8.28%.

Description and references

Prepd by heating aniline with aniline hydrochloride.

Chemical structure

Properties

Crystals; floral odor. d 1.16. mp 53-54°. bp 302°. Flash pt 153°C. Discolors in light. One gram dissolves in 2.2 ml alcohol, 4.5 ml propyl alcohol; freely sol in benzene, ether, glacial acetic acid, carbon disulfide. Insol in water. Forms salts with strong acids. Keep protected from light.

Derivative

Hydrochloride.

Nomenclature

CAS number: 537-67-7
C12H11N.HCl; mol wt 205.68.
C 70.07%, H 5.88%, N 6.81%, Cl 17.24%.

Properties

Crystals, turn blue in air. Freely sol in water, alcohol.

Derivative

Sulfate.

Nomenclature

CAS number: 587-84-8
C12H11N.H2SO4; mol wt 267.30.
C 53.92%, H 4.90%, N 5.24%, S 12.00%, O 23.94%.

Properties

White to yellowish powder, mp 123-125°. Practically insol in water. Sol in alc, in H2SO4.

Caution

Potential symptoms of overexposure to diphenylamine are irritation of eyes, skin, mucous membranes; eczema; tachycardia, hypertension; cough, sneezing; methemoglobinemia; increased blood pressure and heart rate; proteinuria, hematuria, bladder injury. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 120.

Use

Manuf dyes; stabilizing nitrocellulose explosives and celluloid. In analytical chemistry for the detection of NO3, ClO3 and other oxidizing substances with which, in the presence of H2SO4, it gives a deep-blue color. Indicator for redox titrations.

Therapeutic Category (Veterinary)

Topically in antiscrewworm mixtures. In tests for nitrate or nitrite poisoning.