2-Cyanoguanidine

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2-Cyanoguanidine
Skeletal formulaπ Ball-and-stick model
Identifiers
CAS number 461-58-5 YesY
PubChem 10005
ChemSpider 9611 YesY
EC number 207-312-8
RTECS number ME9950000
Jmol-3D images Image 1
Properties
Molecular formula C2H4N4
Molar mass 84.08 g/mol
Appearance White crystals
Density 1.400 g/cm3
Melting point 209.5 °C
Boiling point 252 °C
Solubility in water 41.3 g/l
log P -0.52
kH 2.25·10-10 atm.m³/mol
Hazards
R-phrases R20/21/22
S-phrases S24/25
Main hazards harmful (Xn)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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.[1]

Production and use[edit]

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.[1]

Tautomers and salts[edit]

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 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[2] where we can see the anion depicted as N(CN)2-.

Controversy[edit]

In September 2012, traces of dicyandiamide were found in milk produced by New Zealand company Fonterra.[3] Fonterra, Federated Farmers, and the Government moved quickly to reassure the public and overseas buyers there was no risk to health.[4] Fonterra has received praise for its handling of the DCD issue.[5] The levels were very low and attempts were made to prevent the test results from being reported in the media.[6]

References[edit]

  1. ^ a b Thomas Güuthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2. 
  2. ^ 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.
  3. ^ "Government downplays DCD risk". 3 News NZ. January 27, 2013. 
  4. ^ Astley, Mark (January 28, 2013). "Government defends Fonterra's safety". 3 News NZ. 
  5. ^ "DCD concerns: NZ handling of crisis was ‘textbook’ - Rabobank". Dairy Reporter. February 21, 2013. 
  6. ^ Watkins, Tracy (14 April 2013). "Secrecy Over DCD In Milk Scare Revealed". Sunday Star-Times. Retrieved 13 April 2013. 

External links[edit]