Chemistry:2-Cyanoguanidine
2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared.
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][2]
- (H
2N)
2C=NCN + PhCN → 1,3-(H
2N)-5-Ph(C
3N
3)
Cyanoguanidine is also used as a nitrification inhibitor in stabilized nitrogen fertilizers.[3] It is used in the adhesive industry as a curing agent for epoxy resins.[3] Formerly, it was used as a fuel in some explosives, and may be used as a stabilizer for nitrocellulose.[4]
It was patented for use in the synthesis of methylphenobarbital.[5]
Chemistry
The structure has been confirmed by X-ray crystallography.[6] The molecule is planar with two primary amine groups attached to an imino nitrile. According to Raman spectroscopy measurements, solutions also contain a tautomer, (H
2N)HN=CN(H)CN.[7]
2-cyanoguanidine is isomeric to ammonium dicyanamide, from which it may be prepared by heating in a closed vessel.[3][8] The reaction proceeds via a zwitterionic intermediate, analogous to the Wöhler synthesis of urea from ammonium cyanate.[8]
References
- ↑ Deim, H.; Matthias, G.; Wagner, R. A.. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_115.pub2.
- ↑ Simons, J. K.; Saxton, M. R. (1953). "Benzoguanamine". Org. Synth. 33: 13. doi:10.15227/orgsyn.033.0013. http://www.orgsyn.org/demo.aspx?prep=CV4P0078.; Coll. Vol., 4, 1963, pp. 78
- ↑ 3.0 3.1 3.2 Cite error: Invalid
<ref>tag; no text was provided for refs namedUllmann - ↑ Fedoroff, Basil T.; Sheffield, Oliver E. (1 January 1966). Encyclopedia of Explosives and Related Items: Volume 3 - Chlorides through Detonating Relays. Dover, NJ: Picatinny Arsenal. p. C-587. AD0653029. https://apps.dtic.mil/sti/pdfs/AD0653029.pdf. Retrieved 25 October 2025.
- ↑ Ludwig Taub and Walter Kropp, U.S. Patent 2,061,114 (1936 to Winthrop Chemical Company Inc.).
- ↑ Hirshfeld, F. L.; Hope, H. (1980). "An X-ray determination of the charge deformation density in 2-cyanoguanidine". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 36 (2): 406–415. doi:10.1107/S0567740880003366. Bibcode: 1980AcCrB..36..406H.
- ↑ Alı́a, J.M.; Edwards, H.G.M.; Garcı́a Navarro, F.J. (2001). "The imino–amino tautomeric equilibrium in cyanoguanidine dissolved in several aprotic solvents; an FT-Raman spectroscopic study". Journal of Molecular Structure 597 (1–3): 49–55. doi:10.1016/S0022-2860(01)00579-8. Bibcode: 2001JMoSt.597...49A.
- ↑ 8.0 8.1 Lotsch, Bettina V.; Senker, Jürgen; Schnick, Wolfgang (1 February 2004). "Characterization of the Thermally Induced Topochemical Solid-State Transformation of NH4[N(CN)2 into NCN=C(NH2)2 by Means of X-ray and Neutron Diffraction as Well as Raman and Solid-State NMR Spectroscopy"]. Inorganic Chemistry 43 (3): 895–904. doi:10.1021/ic034984f. https://epub.ub.uni-muenchen.de/14479/1/ic034984f.pdf.
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