Cyanamide Identifiers CAS number PubChem ChemSpider UNII EC number UN number 2811 DrugBank KEGG ChEBI ChEMBL RTECS number GS5950000 Jmol-3D images Image 1 Properties Molecular formula CH2N2 Molar mass 42.040 g/mol Appearance Crystalline solid Density 1.28 g/cm3 Melting point
260 °C (decomp.)
83 °C at 6.7 Pa
140 °C at 2.5 kPa
Solubility in water 85 g/100 ml (25 °C) Solubility in organic solvents soluble Hazards MSDS ICSC 0424 EU Index 615-013-00-2 EU classification Toxic (T) R-phrases , , , S-phrases , , , , NFPA 704 Flash point 141 °C Related compounds Related compounds Calcium cyanamide (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol deterrent drug in Canada, Europe and Japan. The molecule features a nitrile group attached to an amino group. Although it is similar in structure to hydrogen cyanide, it is not as toxic. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
Tautomers and self-condenstations
Containing both a nucleophilic and electrophilic site within the same molecule, cyanamide undergoes various reactions with itself. Cyanamide exists as two tautomers, one with the connectivity NCNH2 and the other with the formula HNCNH ("diimide" tautomer). The NCNH2 form dominates, but in a few reactions (e.g. silylation) the diimide form appears to be important.
Production, reactions, uses
Cyanamide is produced by hydrolysis of calcium cyanamide, which in turn is prepared from calcium carbide via the Frank-Caro process.
- CaCN2 + H2O + CO2 → CaCO3 + H2NCN
The conversion is conducted on slurries, consequently most commercial cyanamide is sold as an aqueous solution.
The main reaction exhibited by cyanamide involves additions of compounds containing an acidic proton. Water, hydrogen sulfide, and hydrogen selenide react with cyanamide to give urea, thiourea, and selenourea, respectively:
- H2NCN + H2E → H2NC(E)NH2 (E = O, S, Se)
In this way, cyanamide behaves as a dehydration agent and thus can induce condensation reactions. Alcohols, thiols, and amines react analogously to give alkylisoureas, "pseudothioureas," and guanidines. The anti-ulcer drug cimetidine is generated using such reactivity. Related reactions exploit the bifunctionality of cyanamide to give heterocycles, and this latter reactivity is the basis of several pharmaceutical syntheses such as the aminopyrimidine imatinib) and agrichemicals Amitrol (3-Amino-1,2,4-triazole) and Hexazinone. The hair-loss treatment Minoxidil and the anthelmintic (worm-killing) drugs Albendazole, Flubendazole, and Mebendazole feature 2-aminoimidazole substructures derived from cyanamide.
Cyanamide (U.S. trade name Dormex) is a common agricultural rest-breaking agent applied in spring to stimulate uniform opening of buds, early foliation and bloom. Dormex can effectively compensate for the moderate lack of chilling units accumulated in the previous autumn and save the harvest that would otherwise be lost. Overdosage, high concentration and error in timing of application can damage the buds (especially of peach trees).
Cyanamide degrades via hydrolysis to urea, an excellent fertilizer. Microorganisms, e.g. the bacterium Myrothecium verrucaria, accelerate this process utilizing the enzyme cyanamide hydratase.
Cyanamide has a modest toxicity in humans. Workplace exposure to hydrogen cyanamide sprays or exposure in people living in the vicinity of spraying have been reported as causing respiratory irritation, contact dermatitis, headache, and gastrointestinal symptoms of nausea, vomiting, or diarrhea.
- Carbamide, synonym of urea
- ^ Thomas Güthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2.
- ^ Powell, A. (1999). Action Program for Dormex Application on Peaches. Auburn University. Retrieved 2010-05-24.
- ^ a b Schep L, Temple W, Beasley M (January 2009). "The adverse effects of hydrogen cyanamide on human health: an evaluation of inquiries to the New Zealand National Poisons Centre". Clinical Toxicology (Philadelphia, PA) 472 (1): 58–60. doi:10.1080/15563650802459254. PMID 18951270.
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