2-cyanoguanidine

2-Cyanoguanidine

Names
IUPAC name 2-Cyanoguanidine
Other names Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
Identifiers
CAS Number	461-58-5 Y
3D model (Jmol)	Interactive image
ChemSpider	9611 Y
ECHA InfoCard	100.006.649
EC Number	207-312-8
PubChem CID	10005
RTECS number	ME9950000
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#C\N=C(/N)N
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
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R-phrases (outdated)	R20/21/22
S-phrases (outdated)	S24/25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).
Y  (what is YN ?)
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.

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.

There are two tautomeric forms, 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]⁻.