| Revision as of 17:17, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476130652 of page 2-Cyanoguanidine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 18:53, 17 June 2024 edit 2.101.54.127 (talk) →Drugs List |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 432649132 |
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|verifiedrevid = 477213177 |
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| ImageFile = CNguanidine.png |
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|ImageFileL1 = CNguanidine.png |
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| ImageSize = 120px |
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|ImageAltL1 = Skeletal formulaπ |
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| IUPACName = 2-Cyanoguanidine |
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|ImageFileR1 = 2-Cyanoguanidine-3D-balls.png |
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| OtherNames = Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy |
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|ImageAltR1 = Ball-and-stick model |
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| Section1 = {{Chembox Identifiers |
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|IUPACName = 2-Cyanoguanidine |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|OtherNames = Cyanoguanidine, dicyanodiamide, ''N''-cyanoguanidine, 1-cyanoguanidine, guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy |
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| ChemSpiderID = 9611 |
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|Section1={{Chembox Identifiers |
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| InChIKey = QGBSISYHAICWAH-UHFFFAOYAY |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 9611 |
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| StdInChI = 1S/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) |
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|ChEBI = 147423 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QGBSISYHAICWAH-UHFFFAOYSA-N |
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|InChIKey = QGBSISYHAICWAH-UHFFFAOYAY |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) |
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| CASNo = 461-58-5 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| EINECS = 207-312-8 |
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|StdInChIKey = QGBSISYHAICWAH-UHFFFAOYSA-N |
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| PubChem = 10005 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = N#C\N=C(/N)N |
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|CASNo = 461-58-5 |
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| InChI = 1/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| RTECS = ME9950000 |
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|UNII = M9B1R0C16H |
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}} |
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|EINECS = 207-312-8 |
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| Section2 = {{Chembox Properties |
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|PubChem = 10005 |
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| Formula = C<sub>2</sub>H<sub>4</sub>N<sub>4</sub> |
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|SMILES = N#CNC(=N)N |
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| MolarMass = 84.08 g/mol |
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|SMILES1 = N#CN=C(N)N |
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| Appearance = White crystals |
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|SMILES1_Comment = isomer |
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| Density = 1.400 g/cm<sup>3</sup> |
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|SMILES2 = N#CNC(=) |
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| MeltingPt = 209.5 °C |
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|SMILES2_Comment = ] |
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| BoilingPt = 252 °C |
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|InChI = 1/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) |
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| Solubility = 41.3 g/l |
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|RTECS = ME9950000 |
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| LogP = -0.52 |
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| HenryConstant = 2.25·10<sup>-10</sup> atm.m³/mol |
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}} |
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| Section7 = {{Chembox Hazards |
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| MainHazards = harmful ('''Xn''') |
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| RPhrases = {{R20/21/22}} |
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| SPhrases = {{S24/25}} |
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| FlashPt = |
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| Autoignition = |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = C<sub>2</sub>H<sub>4</sub>N<sub>4</sub> |
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|MolarMass = 84.08 g/mol |
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|Appearance = White crystals |
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|Density = 1.400 g/cm<sup>3</sup> |
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|MeltingPtC = 209.5 |
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|BoilingPtC = 252 |
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|Solubility = 41.3 g/l |
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|LogP = −0.52 |
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|HenryConstant = {{val|2.25|e=-10|u=atm·m<sup>3</sup>/mol}} |
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|MagSus = {{val|-44.55|e=-6|u=cm<sup>3</sup>/mol}} |
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}} |
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|Section3={{Chembox Hazards |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|302|312|332}} |
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|PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|312|322|330|363|501}} |
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}} |
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}} |
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'''2-Cyanoguanidine''' is a ] derived from ]. It is a ] of ], from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in ], ], and ], but not nonpolar organic solvents.<ref name=Ullmann>{{cite encyclopedia|author= Thomas Güthner |author2= Bernd Mertschenk |title= Cyanamides |encyclopedia= Ullmann's Encyclopedia of Industrial Chemistry |publisher= ] |location= Weinheim |year=2006|doi=10.1002/14356007.a08_139.pub2|isbn= 3527306730}}</ref> |
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==Production and use== |
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2-Cyanoguanidine is produced by treating ] with base. It is produced in soil by decomposition of cyanamide. A variety of useful compounds are produced from 2-cyanoguanidine, ]s and ]. For example, ] and ] are prepared by condensation of cyanoguanidine with the ]:<ref>{{cite encyclopedia|author1=H. Deim |author2=G. Matthias |author3=R. A. Wagner|title=Amino Resins|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2012|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a02_115.pub2|isbn=978-3527306732 }}</ref><ref>{{cite journal|journal=Organic Syntheses|year=1953|volume=33|page=13|doi=10.15227/orgsyn.033.0013|title=Benzoguanamine|author1=J. K. Simons |author2=M. R. Saxton}}</ref> |
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:(H<sub>2</sub>N)<sub>2</sub>C=NCN + RCN → (CNH<sub>2</sub>)<sub>2</sub>(CR)N<sub>3</sub> |
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Cyanoguanidine is also used as a slow ]. Formerly, it was used as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxy resins.<ref name=Ullmann/> |
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==Chemistry== |
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Two ]ic forms exist, differing in the protonation and bonding of the nitrogen to which the ] group is attached. |
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:] |
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2-Cyanoguanidine can also exist in a ]ic form via a formal ] among the nitrogens. |
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:] |
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Loss of ammonia (NH<sub>3</sub>) from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the ] anion, <sup>−</sup>. |
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==Drugs List== |
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2-Cyanoguanidine finds use in the synthesis of the following list of agents: |
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#] (DAM) |
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#]<ref>Ludwig Taub and Walter Kropp, {{US patent|2061114}} (1936 to Winthrop Chemical Company Inc.).</ref> |
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==References== |
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{{Reflist}} |
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==External links== |
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* {{ICSC|0650|06}} |
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* {{Webarchive|url=https://web.archive.org/web/20170517124709/http://www.inchem.org/documents/sids/sids/461585.pdf |date=2017-05-17 }} |
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{{DEFAULTSORT:Cyanoguanidine, 2-}} |
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] |
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] |
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] |