2-Cyanoguanidine

changed 477213177 CNguanidine.png Skeletal formulaπ skin-invert-image 2-Cyanoguanidine-3D-balls.png Ball-and-stick model bg-transparent N′′-Cyanoguanidine Cyanoguanidine Dicyandiamide Dicyanodiamide N-cyanoguanidine 1-cyanoguanidine Guanidine-1-carbonitrile Didin DCD Dicy correct chemspider 9611 147423 QGBSISYHAICWAH-UHFFFAOYAY correct chemspider 1S/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) correct chemspider QGBSISYHAICWAH-UHFFFAOYSA-N correct CAS 461-58-5 correct FDA M9B1R0C16H 207-312-8 10005 N#CNC(=N)N N#CN=C(N)N isomer N#CN=C([NH-])[NH3+] zwitterion 1/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) ME9950000 C2H4N4 2 4 4 White crystals 1.4 g/cm3 209.5 252 14.8 14.4 41.3 g/LThomas Güthner Bernd Mertschenk Cyanamides 10.1002/14356007.a08_139.pub2 soluble acetone soluble ethanol −1.5 (est)0650 06 2.25 -10 atm·m3 molOctober 2025 -44.55 -6 cm3/molOctober 2025 D76609 Dicyandiamide 24 October 2025 >30000 mg/kg none (oral, rat)Sakai akira 30 January 2004 SIDS Initial Assessment Report, Cyanoguanidine http://www.inchem.org/documents/sids/sids/461585.pdf https://web.archive.org/web/20170517124709/http://www.inchem.org/documents/sids/sids/461585.pdf 2017-05-17 SIAM 17 Arona, Italy UNEP Publications 24 October 2025 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:H. Deim G. Matthias R. A. Wagner Amino Resins 10.1002/14356007.a02_115.pub2Simons J. K. Saxton M. R. 1953 Benzoguanamine 33 13 10.15227/orgsyn.033.0013 1963 4 78 CV4P0078 yes (H2N)2C\dNCN + PhCN -> 1,3-(H2N)-5-Ph(C3N3) Cyanoguanidine is also used as a nitrification inhibitor in stabilized nitrogen fertilizers. It is used in the adhesive industry as a curing agent for epoxy resins. Formerly, it was used as a fuel in some explosives, and may be used as a stabilizer for nitrocellulose.Fedoroff Basil T. Sheffield Oliver E. Encyclopedia of Explosives and Related Items: Volume 3 - Chlorides through Detonating Relays 1 January 1966 Picatinny Arsenal Dover, NJ C-587 https://apps.dtic.mil/sti/pdfs/AD0653029.pdf 25 October 2025 AD0653029 It was patented for use in the synthesis of methylphenobarbital.Ludwig Taub and Walter Kropp, 2061114 (1936 to Winthrop Chemical Company Inc.). Chemistry The structure has been confirmed by X-ray crystallography.Hirshfeld F. L. Hope H. An X-ray determination of the charge deformation density in 2-cyanoguanidine Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 1980 36 2 406–415 10.1107/S0567740880003366 1980AcCrB..36..406H The molecule is planar with two primary amine groups attached to an imino nitrile. According to Raman spectroscopy measurements, solutions also contain a tautomer, (H2N)HN\dCN(H)CN.Alı́a J.M. Edwards H.G.M. Garcı́a Navarro F.J. The imino–amino tautomeric equilibrium in cyanoguanidine dissolved in several aprotic solvents; an FT-Raman spectroscopic study Journal of Molecular Structure 2001 597 1–3 49–55 10.1016/S0022-2860(01)00579-8 2001JMoSt.597...49A class=skin-invert-image|300px 2-cyanoguanidine is isomeric to ammonium dicyanamide, from which it may be prepared by heating in a closed vessel. The reaction proceeds via a zwitterionic intermediate, analogous to the Wöhler synthesis of urea from ammonium cyanate.Lotsch Bettina V. Senker Jürgen Schnick Wolfgang 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 1 February 2004 43 3 895–904 10.1021/ic034984f https://epub.ub.uni-muenchen.de/14479/1/ic034984f.pdf https://web.archive.org/web/20170811103009/https://epub.ub.uni-muenchen.de/14479/1/ic034984f.pdf 11 August 2017 References Category:Guanidines Category:Cyanamides Category:Cyanoguanidines Category:Organic compounds with 2 carbon atoms Category:Dimers (chemistry)