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]
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]
Chemistryedit
Two tautomeric forms exist, differing in the protonation and bonding of the nitrogen to which the nitrile group is attached.
Loss of ammonia (NH3) from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the dicyanamide anion, [N(CN)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. ISBN978-3527306732.
^J. K. Simons; M. R. Saxton (1953). "Benzoguanamine". Organic Syntheses. 33: 13. doi:10.15227/orgsyn.033.0013.
cyanoguanidine, nitrile, derived, from, guanidine, dimer, cyanamide, from, which, prepared, colourless, solid, that, soluble, water, acetone, alcohol, nonpolar, organic, solvents, namesiupac, name, other, names, cyanoguanidine, dicyanodiamide, 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 1 2 Cyanoguanidine NamesIUPAC name 2 CyanoguanidineOther names Cyanoguanidine dicyanodiamide N cyanoguanidine 1 cyanoguanidine guanidine 1 carbonitrile dicyandiamin Didin DCD DicyIdentifiersCAS Number 461 58 5 Y3D model JSmol Interactive imageisomer Interactive imagezwitterion Interactive imageChEBI CHEBI 147423ChemSpider 9611 YECHA InfoCard 100 006 649EC Number 207 312 8PubChem CID 10005RTECS number ME9950000UNII M9B1R0C16H YCompTox Dashboard EPA DTXSID1020354InChI InChI 1S C2H4N4 c3 1 6 2 4 5 h H4 4 5 6 YKey QGBSISYHAICWAH UHFFFAOYSA N YInChI 1 C2H4N4 c3 1 6 2 4 5 h H4 4 5 6 Key QGBSISYHAICWAH UHFFFAOYAYSMILES N CNC N Nisomer N CN C N Nzwitterion N CNC N NH3 PropertiesChemical formula C2H4N4Molar mass 84 08 g molAppearance White crystalsDensity 1 400 g cm3Melting point 209 5 C 409 1 F 482 6 K Boiling point 252 C 486 F 525 K Solubility in water 41 3 g llog P 0 52Henry s lawconstant kH 2 25 10 10 atm m3 molMagnetic susceptibility x 44 55 10 6 cm3 molHazardsGHS labelling PictogramsSignal word WarningHazard statements H302 H312 H332Precautionary statements P261 P264 P270 P271 P280 P301 P312 P302 P352 P304 P312 P304 P340 P312 P322 P330 P363 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production and use 2 Chemistry 3 References 4 External linksProduction and use edit2 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 N3Cyanoguanidine 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 editTwo tautomeric forms exist differing in the protonation and bonding of the nitrogen to which the nitrile group is attached nbsp 2 Cyanoguanidine can also exist in a zwitterionic form via a formal acid base reaction among the nitrogens nbsp Loss of ammonia NH3 from the zwitterionic form followed by deprotonation of the remaining central nitrogen atom gives the dicyanamide anion N CN 2 References edit a b Thomas Guthner Bernd Mertschenk 2006 Cyanamides Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a08 139 pub2 ISBN 3527306730 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 J K Simons M R Saxton 1953 Benzoguanamine Organic Syntheses 33 13 doi 10 15227 orgsyn 033 0013 External links editInternational Chemical Safety Card 0650 OECD document Archived 2017 05 17 at the Wayback Machine Entry at chemicalland21 com Retrieved from https en wikipedia org w index php title 2 Cyanoguanidine amp oldid 1175229384, wikipedia, wiki, book, books, library,
