Cyanamide
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| Names | |||
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| IUPAC names
Cyanamide,
aminomethanenitrile | |||
| Other names
Amidocyanogen, carbamonitrile, carbimide, carbodiimide, cyanoamine, cyanoazane, N-cyanoamine, cyanogenamide, cyanogen amide, cyanogen nitride, diiminomethane, hydrogen cyanamide, methane diimide
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| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.006.358 | ||
| EC Number |
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| KEGG | |||
PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 2811 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| CH2N2 | |||
| Molar mass | 42.040 g/mol | ||
| Appearance | Crystalline solid | ||
| Density | 1.28 g/cm3 | ||
| Melting point | 44 °C (111 °F; 317 K) | ||
| Boiling point | 260 °C (500 °F; 533 K) (decomposes) 83 °C at 6.7 Pa 140 °C at 2.5 kPa | ||
| 85 g/100 ml (25 °C) | |||
| Solubility in organic solvents | soluble | ||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 141 °C (286 °F; 414 K) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[1] | ||
REL (Recommended)
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TWA 2 mg/m3 | ||
IDLH (Immediate danger)
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N.D.[1] | ||
| Safety data sheet (SDS) | ICSC 0424 | ||
| Related compounds | |||
Related compounds
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Calcium cyanamide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[citation needed] 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-condensations
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.
Cyanamide dimerizes to give 2-cyanoguanidine (dicyandiamide). This decomposition process is disfavored by acids and is inhibited by low temperatures. The cyclic trimer is called melamine.
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.[2]
Cyanamide is a common agricultural rest-breaking agent applied in spring to stimulate uniform opening of buds, early foliation and bloom. Cyanamide can effectively compensate for the moderate lack of chilling units accumulated in the previous autumn and save the harvest that would otherwise be lost. It is particularly effective for woody plants such as berries, grapes, apples, peaches and kiwifruit. Overdosage, high concentration and error in timing of application can damage the buds (especially of peach trees).[3]
Environmental aspects
Cyanamide degrades via hydrolysis to urea, an excellent fertilizer. Fungi, like Myrothecium verrucaria, accelerate this process utilizing the enzyme cyanamide hydratase.[4]
Safety
Cyanamide has a modest toxicity in humans.[5] 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.[5]
References
- ^ a b NIOSH Pocket Guide to Chemical Hazards. "#0160". National Institute for Occupational Safety and Health (NIOSH).
- ^ 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.
- ^ Stransky H and Amberger A (1973). "Isolation and properties of a cyanamide hydratase (EC 4.2.1) from Myrothecium verrucaria". Z. Pflanzenphysiol. 70: 74–87.
- ^ 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. 472 (1). Philadelphia, PA: 58–60. doi:10.1080/15563650802459254. PMID 18951270.
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External links
- International Chemical Safety Card 0424
- NIOSH Pocket Guide to Chemical Hazards. "#0160". National Institute for Occupational Safety and Health (NIOSH).
- OSHA guideline for cyanamide
