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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