1,1'-Azobis(cyanocyclohexane)

Chemical Properties

faintly beige crystalline powder

Uses

A more efficient radical initiator than AIBN has been employed to initiate primary radical reactions.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2661, 1949 DOI: 10.1021/ja01176a018
Organic Syntheses, Coll. Vol. 4, p. 66, 1963

General Description

A white to light colored solid substance. Insoluble in water and more dense that water. May cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. If exposed to high temperatures or flames 1,1'-Azobis(cyanocyclohexane) may ignite and burn with an intense flame. Dust may form an explosive mixture in air.

Air & Water Reactions

Dust may form an explosive mixture in air. Insoluble in water.

Reactivity Profile

Self-decomposition or self-ignition may be triggered by heat, chemical reaction, friction or impact. May be ignited by heat, sparks or flames. 1,1'-Azobis(cyanocyclohexane) is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Health Hazard

Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.

Purification Methods

Purify the nitrile by dissolving it in boiling 95%EOH as rapidly as possible, cool overnight at 0o, filter, wash with a little EtOH and dry it in a vacuum desiccator over CaCl2. Note that prolonged heating >80o causes decomposition. Recrystallise it from EtOH. It should be regarded as potentially explosive. It is a radical initiator. [Overberger et al. Org Synth Coll Vol IV 66 1963, Beilstein 16 II 97.]