2-Cyanoguanidine is a

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...

derived from

guanidine Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experie ...

. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in

water Water (chemical formula ) is an Inorganic compound, inorganic, transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living ...

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...

, and alcohol, but not nonpolar organic solvents.

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,

s and

melamine Melamine is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millio ...

. For example, acetoguanamine and

benzoguanamine Benzoguanamine is an organic compound with the chemical formula (CNH2)2(CC6H5)N3. It is related to melamine but with one amino group replaced by phenyl. Benzoguanamine is used in the manufacturing of melamine resins. Unlike melamine ((CNH2)3N3), ...

are prepared by condensation of cyanoguanidine with the

: :(H₂N)₂C=NCN + RCN → (CNH₂)₂(CR)N₃ Cyanoguanidine is also used as a slow

fertilizer A fertilizer (American English) or fertiliser (British English; see spelling differences) is any material of natural or synthetic origin that is applied to soil or to plant tissues to supply plant nutrients. Fertilizers may be distinct from ...

. Formerly, it was used as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxy resins.

Chemistry

Two

tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...

ic forms exist, differing in the protonation and bonding of the nitrogen to which the

group is attached. : Dicyandiamide tautomerism

2-Cyanoguanidine can also exist in a

zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium wil ...

ic form via a formal acid–base reaction among the nitrogens. : Cyanoguanidine zwitterion

Loss of ammonia (NH₃) from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the

dicyanamide Dicyanamide, also known as dicyanamine, is an anion having the formula . It contains two cyanide groups bound to a central nitrogen anion. The chemical is formed by decomposition of 2-cyanoguanidine. It is used extensively as a counterion of orga ...

anion, (CN)₂sup>−.

References

External links

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OECD document

{{DEFAULTSORT:Cyanoguanidine, 2- Guanidines Cyanamides Cyanoguanidines