918. 2,2′-Azobisisobutyronitrile

Nomenclature

CAS number: 78-67-1
2,2′-Azobis[2-methylpropanenitrile]; AIBN; α,α′-azodiisobutyronitrile; 2,2′-dicyano-2,2′-azopropane; Porofor-57.
C8H12N4; mol wt 164.21.
C 58.51%, H 7.37%, N 34.12%.

Description and references

Prepn by oxidation of α,α′-hydrazobutyric acid dinitrile: Overberger et al., J. Am. Chem. Soc. 71, 2661 (1949); Horner, Schwenk, Ann. 566, 69 (1950); from 2-aminoisobutyronitrile + NaOCl: GB 672106 (1952 to Rohm & Haas); Anderson, US 2711405 (1955 to du Pont); from 2,2′-dichloro-2,2′-azopropane: Benzing, Ann. 631, 1 (1960); GB 929182 (1963 to Monsanto).

Chemical structure

Properties

Crystals from ethanol + water, dec 107°. uv max (ethanol): 345 nm. Soly in methanol at 0°, 20°, 40°: 1.8, 4.96, 16.06 g/100 ml. Soly in ethanol at 0°, 20°, 40°: 0.58, 2.04, 7.15 g/100 ml. Can explode when dissolved in acetone: Carlisle, Chem. Eng. News 27, 150 (1949).

Caution

In the organism, forms HCN which is found in blood, liver and brain: Rusin, C.A. 56, 2682f (1962).

Use

Blowing agent for elastomers and plastics. Initiator for free radical reactions: Griesbaum et al., J. Org. Chem. 30, 261 (1965).