2-Cyanoguanidine
2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared.
Production and use
2-Cyanoguanidine is produced by treating cyanamide with base. It is produced in soil by decomposition of cyanamide. A variety of useful compounds are produced from 2-cyanoguanidine, guanidines and melamine. For example, acetoguanamine and benzoguanamine are prepared by condensation of cyanoguanidine with the nitrile:Cyanoguanidine is also used as a nitrification inhibitor in stabilized nitrogen fertilizers. It is used in the adhesive industry as a curing agent for epoxy resins. Formerly, it was used as a fuel in some explosives, and may be used as a stabilizer for nitrocellulose.
It was patented for use in the synthesis of methylphenobarbital.
Chemistry
The structure has been confirmed by X-ray crystallography. The molecule is planar with two primary amine groups attached to an imino nitrile. According to Raman spectroscopy measurements, solutions also contain a tautomer,.2-cyanoguanidine is isomeric to ammonium dicyanamide, from which it may be prepared by heating in a closed vessel. The reaction proceeds via a zwitterionic intermediate, analogous to the Wöhler synthesis of urea from ammonium cyanate.