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| Names | |
|---|---|
| IUPAC name 2-Cyanoguanidine | |
| Other names Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.006.649 
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| EC Number |
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| PubChem CID | |
| RTECS number |
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| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C2H4N4 |
| Molar mass | 84.08 g/mol |
| Appearance | White crystals |
| Density | 1.400 g/cm |
| Melting point | 209.5 °C |
| Boiling point | 252 °C |
| Solubility in water | 41.3 g/l |
| log P | -0.52 |
| Henry's law constant (kH) |
2.25·10 atm.m³/mol |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
| Main hazards | harmful (Xn) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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Infobox references
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2-Cyanoguanidine or commonly dicyanamide is an 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 in diethyl ether or chloroform.
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. It is also used as a slow fertilizer. Formerly, it was as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxies.
Tautomers and salts
It is possible to draw a tautomer of 2-cyanoguanidine with the structure NC-NH-C(NH)NH2. Further tautomerization gives NC-NH-C(N)NH3. Formal loss of neutral ammonia (NH3) from this latter tautomer followed by deprotonation gives the anion commonly referred to the dicyanamide ion, (NC)2N. The dicyanamide ion has been used extensively as a counterion in the chemistry of organic and inorganic salts, for example in the synthesis of what was, in 1990, a superconductor with novel properties where we can see the anion depicted as N(CN)2.
References
- Thomas Güuthner (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2.
{{cite encyclopedia}}: Unknown parameter|coauthor=ignored (|author=suggested) (help) - A new ambient-pressure organic superconductor, κ-(ET)2CuBr, with the highest transition temperature yet observed (inductive onset Tc= 11.6 K, …, AM Kini, U Geiser, HH Wang, KD Carlson…, Inorganic Chemistry 1990, 29, 2555-2557.