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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.[1]

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:[2][3]

(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.[1]

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:

  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[4]
  16. Moroxydine
  17. Oxonazine
  18. Phenformin
  19. Phenylbiguanide
  20. NSC-127755
  21. Triazinate

References

  1. ^ a b Thomas Güthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2. ISBN 3527306730.
  2. ^ H. Deim; G. Matthias; R. A. Wagner (2012). "Amino Resins". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_115.pub2. ISBN 978-3527306732.
  3. ^ J. K. Simons; M. R. Saxton (1953). "Benzoguanamine". Organic Syntheses. 33: 13. doi:10.15227/orgsyn.033.0013.
  4. ^ Ludwig Taub and Walter Kropp, U.S. patent 2,061,114 (1936 to Winthrop Chemical Company Inc.).

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