Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
|Molar mass||84.08 g/mol|
|Melting point||209.5 °C (409.1 °F; 482.6 K)|
|Boiling point||252 °C (486 °F; 525 K)|
|Main hazards||harmful (Xn)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
2-Cyanoguanidine 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 nonpolar organic solvents.
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 used as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxies.
Tautomers and salts
One tautomer of 2-cyanoguanidine has the connectivity NC-NH-C(NH)NH2. Further tautomerization gives NC-NH-C(N−)NH3+. Formal loss of ammonia (NH3) from this latter tautomer, followed by deprotonation gives the dicyanamide anion, [N(CN)2]−. The dicyanamide anion has been used extensively as a counterion of organic and inorganic salts, such as in the synthesis of what was, in 1990, a superconductor with novel properties.
In September 2012, traces of dicyandiamide were found in milk produced by New Zealand company Fonterra. Fonterra, Federated Farmers, and the Government moved quickly to reassure the public and overseas buyers there was no risk to health. Fonterra has received praise for its handling of the DCD issue. The levels were very low and attempts were made to prevent the test results from being reported in the media.
- Thomas Güuthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2.
- Shapiro, S. L.; Parrino, V. A.; Freedman, L. (1959). "Hypoglycemic Agents. III.1—3N1-Alkyl- and Aralkylbiguanides". Journal of the American Chemical Society 81 (14): 3728. doi:10.1021/ja01523a060.
- A new ambient-pressure organic superconductor, κ-(ET)2Cu[N(CN)2]Br, 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.
- "Government downplays DCD risk". 3 News NZ. January 27, 2013.
- Astley, Mark (January 28, 2013). "Government defends Fonterra's safety". 3 News NZ.
- "DCD concerns: NZ handling of crisis was ‘textbook’ - Rabobank". Dairy Reporter. February 21, 2013.
- Watkins, Tracy (14 April 2013). "Secrecy Over DCD In Milk Scare Revealed". Sunday Star-Times. Retrieved 13 April 2013.