2-Cyanoguanidine

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]

2-Cyanoguanidine
Skeletal formulaπ
Ball-and-stick model
Names
IUPAC name
2-Cyanoguanidine
Other names
Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.649
EC Number
  • 207-312-8
RTECS number
  • ME9950000
UNII
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
2.25·10−10 atm.m3/mol
-44.55·10−6 cm3/mol
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 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).
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Infobox references

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]−.

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References
  1. 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.
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