2-Cyanoguanidine

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:
 * (H2N)2C=NCN + RCN → (CNH2)2(CR)N3

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.
 * Dicyandiamide tautomerism.png

2-Cyanoguanidine can also exist in a zwitterionic form via a formal acid–base reaction among the nitrogens.


 * Cyanoguanidine zwitterion.png

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:
 * 1) Amanozine
 * 2) Azapropazone
 * 3) Buformin
 * 4) Chlorazanil
 * 5) Chlorproguanil
 * 6) Clociguanil
 * 7) Cloguanamil
 * 8) Cloquanamil
 * 9) Cycloguanil
 * 10) Dametralast
 * 11) Diallylmelamine (DAM)
 * 12) Guanazole
 * 13) Irsogladine
 * 14) Metformin
 * 15) Methylphenobarbital
 * 16) Moroxydine
 * 17) Oxonazine
 * 18) Phenformin
 * 19) Phenylbiguanide
 * 20) NSC-127755
 * 21) Triazinate