2-Cyanoguanidine

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:

: 1,3--5-

Cyanoguanidine is also used as a nitrification inhibitor in stabilized nitrogen fertilizers.

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, . :[[File:Dicyandiamide tautomerism.png|class=skin-invert-image|300px]]

2-cyanoguanidine is isomeric to ammonium dicyanamide, from which it may be prepared by heating in a closed vessel.

References

References

1. "Cyanamides".
2. {{ICSC. 0650. 06
3. {{Sigma-Aldrich
4. Sakai, akira. (30 January 2004). "SIDS Initial Assessment Report, Cyanoguanidine". UNEP Publications.
5. "Amino Resins".
6. (1953). "Benzoguanamine".
7. (1 January 1966). "Encyclopedia of Explosives and Related Items: Volume 3 - Chlorides through Detonating Relays". Picatinny Arsenal.
8. Ludwig Taub and Walter Kropp, {{US patent. 2061114 (1936 to Winthrop Chemical Company Inc.).
9. (1980). "An X-ray determination of the charge deformation density in 2-cyanoguanidine". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry.
10. (2001). "The imino–amino tautomeric equilibrium in cyanoguanidine dissolved in several aprotic solvents; an FT-Raman spectroscopic study". Journal of Molecular Structure.