Cinnamonitrile

Chemical properties

Clear colourless to yellow liquid, ractical}y insoluble in water, soluble in alcohol and oils.

Occurrence

Has apparently not been reported to occur in nature.

The Uses of Cinnamonitrile

Cinnamonitrile is a parent compound whose derivatives can be applied as corrosion inhibitors for API J55 steel.

The Uses of Cinnamonitrile

The parent compound whose derivatives can be applied as corrosion inhibitors for API J55 steel.

Preparation

From styryl bromide and potassium cyanide (Arctander, 1969).

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 6340, 1959 DOI: 10.1021/ja01532a069
Tetrahedron Letters, 21, p. 2161, 1980 DOI: 10.1016/S0040-4039(00)78986-6

Toxicity evaluation

The acute oral LD₅₀ value in rats was reported as 4.15g/kg (3.67-4.63 g/kg) and the acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Moreno, 1974). In rabbits, iv injection of cinnamyl nitrile (20.3 mg/kg) caused death in 10 min. In guinea-pigs and rabbits, cinnamyl nitrile was found to produce the same effects as hydrogen cyanide, with almost equal toxicity, and rabbits given doses higher than the lethal dose were found to die almost as rapidly as those given hydrogen cyanide (Hunt, 1923).

Flammability and Explosibility

Not classified

Metabolism

The toxicity of organic cyanides appears to depend almost entirely on whether they can be metabolized in the body to the free cyanide ion, and on the rate and extent of this conversion and the rate of detoxication of cyanide to thiocyanate. In general, alkyl and arylalkyl cyanides are metabolized with the formation of hydrogen cyanide, while the nitrile group of aryl cyanides is relatively stable. The high toxicity of iv-administered cinnamyl nitrile and the rapidity of death suggest that in rabbits this compound is metabolically converted to hydrogen cyanide (Hunt, 1923; Williams, 1959).