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Skeletal formulaπ
Ball-and-stick model
IUPAC name
Other names
Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
3D model (JSmol)
ECHA InfoCard 100.006.649
EC Number 207-312-8
RTECS number ME9950000
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
2.25·10−10 atm.m3/mol
-44.55·10−6 cm3/mol
Main hazards harmful (Xn)
R-phrases (outdated) R20/21/22
S-phrases (outdated) S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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[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, 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]


Two tautomeric forms exist, differing in the protonation and bonding of the nitrogen to which the nitrile group is attached.

Dicyandiamide tautomerism.png

2-Cyanoguanidine can also exist in a zwitterionic form via a formal acid–base reaction among the nitrogens.

Cyanoguanidine zwitterion.png

Loss of ammonia (NH3) from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the dicyanamide anion, [N(CN)2].


  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. ^ 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. 
  3. ^ J. K. Simons, M. R. Saxton (1953). "Benzoguanamine". Organic Syntheses. 33: 13. doi:10.15227/orgsyn.033.0013. 

External links[edit]