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

Names
IUPAC name 2-Cyanoguanidine
Other names Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, guanidine-1-carbonitrile, dicyanamide, Didin, DCD, Dicy
Identifiers
CAS Number	461-58-5 Y
3D model (JSmol)	Interactive image isomer: Interactive image zwitterion: Interactive image
ChEBI	CHEBI:147423
ChemSpider	9611 Y
ECHA InfoCard	100.006.649
EC Number	207-312-8
PubChem CID	10005
RTECS number	ME9950000
UNII	M9B1R0C16H Y
CompTox Dashboard (EPA)	DTXSID1020354
InChI InChI=1S/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) Y Key: QGBSISYHAICWAH-UHFFFAOYSA-N Y InChI=1/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) Key: QGBSISYHAICWAH-UHFFFAOYAY
SMILES N#CNC(=N)N isomer: N#CN=C(N)N zwitterion: N#CNC(=[N-])[NH3+]
Properties
Chemical formula	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)
Solubility in water	41.3 g/l
log P	−0.52
Henry's law constant (kH)	2.25×10−10 atm·m3/mol
Magnetic susceptibility (χ)	−44.55×10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Y verify (what is YN ?) 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]⁻.

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^[4]
16. Moroxydine
17. Oxonazine
18. Phenformin
19. Phenylbiguanide
20. NSC-127755
21. Triazinate