2-Cyanoguanidine
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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: | |||
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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).
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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]
Production and use
[edit]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
[edit]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
[edit]2-Cyanoguanidine finds use in the synthesis of the following list of agents:
- Amanozine
- Azapropazone
- Buformin
- Chlorazanil
- Chlorproguanil
- Clociguanil
- Cloguanamil
- Cloquanamil
- Cycloguanil
- Dametralast
- Diallylmelamine (DAM)
- Guanazole
- Irsogladine
- Metformin
- Methylphenobarbital[4]
- Moroxydine
- Oxonazine
- Phenformin
- Phenylbiguanide
- NSC-127755
- Triazinate
References
[edit]- ^ a b Thomas Güthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2. ISBN 3527306730.
- ^ 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.
- ^ J. K. Simons; M. R. Saxton (1953). "Benzoguanamine". Organic Syntheses. 33: 13. doi:10.15227/orgsyn.033.0013.
- ^ Ludwig Taub and Walter Kropp, U.S. patent 2,061,114 (1936 to Winthrop Chemical Company Inc.).