2-Cyanoguanidine

2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not nonpolar organic solvents.

It is used in the adhesive industry as a curing agent for epoxy resins.

[1] 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]−.

Skeletal formulaπ
Ball-and-stick model