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2-Cyanoguanidine

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.649 Edit this at Wikidata
EC Number
  • 207-312-8
PubChem CID
RTECS number
  • ME9950000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6)Key: QGBSISYHAICWAH-UHFFFAOYSA-N
  • InChI=1/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6)Key: QGBSISYHAICWAH-UHFFFAOYAY
SMILES
Properties
Chemical formula C2H4N4
Molar mass 84.08 g/mol
Appearance White crystals
Density 1.400 g/cm
Melting point 209.5 °C (409.1 °F; 482.6 K)
Boiling point 252 °C (486 °F; 525 K)
Solubility in water 41.3 g/l
log P −0.52
Henry's law
constant (kH) 		2.25×10 atm·m/mol
Magnetic susceptibility (χ) −44.55×10 cm/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H312, H332
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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:

(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.

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, .

Drugs List

2-Cyanoguanidine finds use in the synthesis of the following list of agents:

  1. Amanozine
  2. Azapropazone
  3. Buformin
  4. Chlorazanil
  5. Chlorproguanil
  6. Clociguanil
  7. Cloguanamil
  8. Cloquanamil
  9. Cycloguanil
  10. Dametralast
  11. Diallylmelamine (DAM)
  12. Guanazole
  13. Irsogladine
  14. Metformin
  15. Methylphenobarbital
  16. Moroxydine
  17. Oxonazine
  18. Phenformin
  19. Phenylbiguanide
  20. NSC-127755
  21. Triazinate

References

  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.
  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. ISBN 978-3527306732.
  3. J. K. Simons; M. R. Saxton (1953). "Benzoguanamine". Organic Syntheses. 33: 13. doi:10.15227/orgsyn.033.0013.
  4. Ludwig Taub and Walter Kropp, U.S. patent 2,061,114 (1936 to Winthrop Chemical Company Inc.).

External links

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