3-Cyanopyridine

Chemical Properties

The cyanopyridines are as follows: 2-cyano-: A white to tan liquid or solid. Almond odor. Boiling point=2213℃ ; freezing/melting point=27℃ ; flash point=89℃ . 3-cyano-: a colorless liquid or gray crystal- line solid.

Chemical Properties

white to beige solid

Uses

3-Cyanopyridine is used in the preparation of arylthiazolines and arylimidazolines via dibromodimethylhydantoin-catalyzed condensation of aryl nitriles with ethylene diamine or aminoethanethiol.

Definition

ChEBI: A nitrile that is pyridine substituted by a cyano group at position 3.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 2155, 1988 DOI: 10.1016/S0040-4039(00)86697-6

Potential Exposure

Limits in Air NIOSH IDLH525 mg/m3 NIOSH REL: (nitriles) 2 ppm, Ceiling Concentration, not to be exceeded in any 15-minute work period.

Shipping

UN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5).

Purification Methods

It is recrystallised to constant melting point from o-xylene/hexane. [Beilstein 22/2 V 115.]

Incompatibilities

Oxidizing agents, such as perchlorates, peroxides, and permanganates. Nitriles 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 car- boxylic 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 .