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Names | |||
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IUPAC name
2-Cyanoguanidine
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Other names
Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
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Identifiers | |||
3D model (
JSmol)
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ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.006.649 | ||
EC Number |
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PubChem
CID
|
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RTECS number |
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UNII | |||
CompTox Dashboard (
EPA)
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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 | ||
Henry's law
constant (kH) |
2.25×10−10 atm·m3/mol | ||
−44.55×10−6 cm3/mol | |||
Hazards | |||
GHS labelling: | |||
Warning | |||
H302, H312, H332 | |||
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).
|
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 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]
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.
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−.
2-Cyanoguanidine finds use in the synthesis of the following list of agents:
| |||
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 |
| ||
PubChem
CID
|
|||
RTECS number |
| ||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
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 | ||
Henry's law
constant (kH) |
2.25×10−10 atm·m3/mol | ||
−44.55×10−6 cm3/mol | |||
Hazards | |||
GHS labelling: | |||
Warning | |||
H302, H312, H332 | |||
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).
|
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 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]
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.
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−.
2-Cyanoguanidine finds use in the synthesis of the following list of agents: