7283. m-Phenylenediamine

Nomenclature

CAS number: 108-45-2
1,3-Benzenediamine; m-diaminobenzene.
C6H8N2; mol wt 108.14.
C 66.64%, H 7.46%, N 25.90%.

Description and references

Prepd by the reduction of m-dinitrobenzene: Kuhn, US 2768209 (1956 to Ringwood); Faust, J. Prakt. Chem. 6, 14 (1958); Neilson et al., J. Chem. Soc. 1962, 371; Tallee, Peltier, Compt. Rend. 259, 400 (1964). Toxicity study: C. Burnett et al., J. Toxicol. Environ. Health 2, 657 (1977).

Chemical structure

Properties

White crystals becoming red on exposure to air. d 1.139; mp 62-63°; bp 284-287°; dipole moment 1.79. Fire point: 175°. Sol in water, methanol, ethanol, chloroform, acetone, dimethylformamide, methyl ethyl ketone, dioxane. Slightly sol in ether, carbon tetrachloride, dibutyl phthalate, isopropanol. Very slightly sol in benzene, toluene, xylene, butanol. Keep well closed and protected from light. LD50 in rats (mg/kg): 650 orally; 283 i.p. (Burnett).

Derivative

Hydrochloride.

Properties

White or slightly red, crystalline powder; becomes darker on exposure to air. Freely sol in water; sol in alcohol.

Use

Manuf dyes; rubber curing agents, ion exchange resins, decolorizing resins, formaldehyde condensates, resinous polyamides, block polymers, textile fibers, urethanes, petroleum additives, rubber chemicals, corrosion inhibitors; in photography; as reagent for gold and bromine. The hydrochloride chiefly as a reagent for nitrite.