1867.] 



Homologous to Hydrocyanic Acid. 



149 



interrupt for tlie time the preparation in the pure state of the cyanide of 

 ethyl, and to resume it at a more favourable season. 



I was nevertheless curious to study, even now, a true homologue of 

 cyanide of ethyl in order to compare its properties with those of cyanide of 

 phenyl. The boiling-points of the amy lie compounds being within con- 

 venient limits, I was induced to select the amyl-series as presenting the 

 greatest chance of success. 



On submitting amylamine to the action of chloroform, the same pheno- 

 mena are observed as in the analogous reaction between chloroform and 

 aniline. One molecule of amylamine and one molecule of chloroform con- 

 tain the elements of one molecule of cyanide of amyl and three of hydro- 

 chloric acid : — 



C^H.gN + CHCI3 = C^H^.N + SHCl. 



Amylamine. Chloroform. Cyanide of amyl. 



The cyanide of amyl is a transparent colourless liquid lighter than water, 

 insoluble in water, but dissolved by alcohol and ether, of an oppressive odour, 

 resembling at the same time that ofamylic alcohol and of hydrocyanic acid. 

 Its vapour possesses, in a still higher degree than that of the cyanide of 

 phenyl, the property of producing on the tongue an insupportably bitter 

 taste, and of giving rise in the throat to the sensation of suffocation, so 

 characteristic of hydrocyanic acid. 



The cyanide of amyl may be distilled without decomposition. It boils 

 at 137° C, that is, at a temperature 8° lower than the boiling-point of its 

 isomer, capronitrile. It will be remembered that the boiling-point of 

 cyanide of phenyl is lower than that of benzonitrile. 



Under the influence of alkalies and acids, the cyanide of amyl behaves in 

 the same manner as the phenylic cyanide. Though only slightly attacked 

 by alkalies, it is decomposed by acids with a violence which is almost ex- 

 plosive ; a short ebullition with water is sufficient to transform it into for- 

 mic acid and amylamine : — 



C^H^.N + 211,0 = CH^O, + C,H,3N. 



, Cyanide of amyl. Formic acid. Amylamine. 



In order to fix this equation by numbers, I have carried out the reaction 

 by means of dilute sulphuric acid. The formic acid was then distilled off 

 and transformed into a sodium-salt, and analyzed as formate of silver ; the 

 residue in the retort furnished, on addition of an alkali, amylamine in 

 considerable quantities. It was identified with that obtained from cyanate 

 of amyl, both by the determination of its boihng-point and by the analysis 

 of the platinum-salt. 



The transformation of the cyanide of amyl, like that of the cyanide of 

 phenyl, docs not take place at a single step ; intermediate combinations 

 corresponding to methenyldiphenyldiamine and to phenylformamide are 

 produced, but I have not yet obtained them in a state of purity. 



