Chemistry:2-Cyanoguanidine
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| Names | |||
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| IUPAC name
2-Cyanoguanidine
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| Other names
Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
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| Properties | |||
| C2H4N4 | |||
| Molar mass | 84.08 g/mol | ||
| Appearance | White crystals | ||
| Density | 1.400 g/cm3 | ||
| Melting point | 209.5 °C (409.1 °F; 482.6 K) | ||
| Boiling point | 252 °C (486 °F; 525 K) | ||
| 41.3 g/l | |||
| log P | −0.52 | ||
Henry's law
constant (kH) |
2.25×10−10 atm·m3/mol | ||
| −44.55×10−6 cm3/mol | |||
| Hazards | |||
| GHS pictograms | 
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| GHS Signal word | Warning | ||
| H302, H312, H332 | |||
| P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is   ?)
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| Infobox references | |||
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]
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:[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]
Chemistry
Two tautomeric forms exist, differing in the protonation and bonding of the nitrogen to which the nitrile group is attached.
2-Cyanoguanidine can also exist in a zwitterionic form via a formal acid–base reaction among the nitrogens.
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
- ↑ 1.0 1.1 Thomas Güthner; 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.
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