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
Dimer may refer to:
* Dimer (chemistry), a chemical structure formed from two similar sub-units
** Protein dimer, a protein quaternary structure
** d-dimer
* Dimer model, an item in statistical mechanics, based on ''domino tiling''
* Julius Dimer ...
of
cyanamide
Cyanamide is an organic compound with the chemical formula, formula carbon, Cnitrogen, N2hydrogen, H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcoho ...
, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in
water
Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...
,
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 miscib ...
, and
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
, but not nonpolar organic solvents.
Production and use
2-Cyanoguanidine is produced by treating
cyanamide
Cyanamide is an organic compound with the chemical formula, formula carbon, Cnitrogen, N2hydrogen, H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcoho ...
with base. It is produced in soil by decomposition of cyanamide. A variety of useful compounds are produced from 2-cyanoguanidine,
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 ...
s and
melamine
Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire retardant properties due t ...
. 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
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 ...
:
:(H
2N)
2C=NCN + RCN → (CNH
2)
2(CR)N
3
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 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 ...
group is attached.
:
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
An acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their applica ...
among the nitrogens.
:
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 org ...
anion, 2">(CN)2sup>−.
References
External links
*
OECD document
{{DEFAULTSORT:Cyanoguanidine, 2-
Guanidines
Cyanamides
Cyanoguanidines