p-Tolunitrile

Chemical properties

This substance is a clear colorless liquid or beige solid that exhibits toxicity and flammability. It should avoid contact with the skin.

The Uses of p-Tolunitrile

p-?Tolunitrile is a reagent used in the preparation of 1H-Indazoles from imidates and nitrosobenzenes.

Synthesis Reference(s)

Synthetic Communications, 15, p. 1299, 1985 DOI: 10.1080/00397918508077278
Tetrahedron Letters, 27, p. 1925, 1986 DOI: 10.1016/S0040-4039(00)84413-5

General Description

Beige solid at 62.6° F.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitriles, such as p-Tolunitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Fire Hazard

p-Tolunitrile is combustible.

Purification Methods

Melt the nitrile, dry it with MgSO4, fractionally crystallise it from its melt, then fractionally distil it under reduced pressure in a 6-in spinning band column. [Brown J Am Chem Soc 81 3232 1959.] It can also be crystallised from *benzene/pet ether (b 40-60o). [Beilstein 9 H 489, 9 I 194, 9 II 330, 9 III 2348, 9 IV 1738.]