2-Cyanoguanidine

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2-Cyanoguanidine
Skeletal formulaπ
Ball-and-stick model
Names
IUPAC name
2-Cyanoguanidine
Other names
Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
Identifiers
461-58-5 YesY
ChemSpider 9611 YesY
EC Number 207-312-8
Jmol 3D model Interactive image
PubChem 10005
RTECS number ME9950000
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
2.25·10−10 atm.m3/mol
Hazards
Main hazards harmful (Xn)
R-phrases R20/21/22
S-phrases S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2-Cyanoguanidine is an 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. 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.[1]

Chemistry[edit]

There are two tautomeric forms, differing in the protonation and bonding of the nitrogen to which the nitrile group is attached.

Dicyandiamide tautomerism.png

2-Cyanoguanidine can also exist in a zwitterionic form via a formal acid–base reaction among the nitrogens.

Cyanoguanidine zwitterion.png

Loss of ammonia (NH3) from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the dicyanamide anion, [N(CN)2].

References[edit]

  1. ^ a b Thomas Güuthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2. 

External links[edit]