Toluidine

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Toluidine

 

any of three amino derivatives of toluene.

Ortho, meta, and para isomers of toluidines are known (see Table 1). Toluidines are readily soluble in organic solvents but poorly soluble in water; they may be steam-distilled, and they darken (oxidize) upon storage in light in the presence of air.

Toluidines are obtained industrially by the reduction of nitro-toluenes using iron and hydrochloric acid. They are similar to aniline in their chemical properties. They form salts with acids and

Table 1. Selected properties of toluidines
 Melting point (°C)Boiling point (°C)Density at 20°C (g/cm3)
Ortho-toluidine(1,2-). . . . . . . . . .–24,4 (unstable)200.30.9984
Ortho-toluidine (1,6-). . . . . . . . . .–16.25 (stable)200.30.9984
Mete-toluidine(1,3-or 1,5-). . . . . . . . . .–30.4203.40.9891
Para-toluidine (1,4-). . . . . . . . . .44.5–45,0200.551.046

undergo diazotization, acylation, halogenation, sulfonation, and alkylation. Toluidines are used in the manufacture of various dyes.

B. L. DIATKIN