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 ;
3D model (JSmol)	Interactive image; isomer: Interactive image; zwitterion: Interactive image;
ChEBI	CHEBI:147423;
ChemSpider	9611 ;
ECHA InfoCard	100.006.649
EC Number	207-312-8;
PubChem CID	10005;
RTECS number	ME9950000;
UNII	M9B1R0C16H ;
CompTox Dashboard (EPA)	DTXSID1020354 ;
	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 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). verify (what is ?) 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.^[1]

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:

References

^ ^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.).

External links

International Chemical Safety Card 0650
OECD document Archived 2017-05-17 at the Wayback Machine
Entry at chemicalland21.com

[Ullmann-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.).

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