2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not nonpolar organic solvents.

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 slow fertilizer. Formerly, it was used as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxy resins.

Chemistry

Two tautomeric forms exist, differing in the protonation and bonding of the nitrogen to which the nitrile group is attached. 2-Cyanoguanidine can also exist in a zwitterionic form via a formal acid–base reaction among the nitrogens. Loss of ammonia (NH3) from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the dicyanamide anion, [N(CN)2]−.

Drugs List

2-Cyanoguanidine finds use in the synthesis of the following list of agents: