Sodium cyanate
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.011.846 |
| EC Number | 213-030-6 |
| MeSH | C009281 |
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PubChem CID
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| Properties | |
| NaOCN | |
| Molar mass | 65.01 g/mol |
| Appearance | white crystalline solid |
| Odor | odorless |
| Density | 1.893 g/cm3 |
| Melting point | 550 °C (1,022 °F; 823 K) |
| 11.6 g/100 mL (25 °C) | |
| Solubility |
ethanol: 0.22 g/100 mL (0 °C) dimethylformamide: 0.05 g/100 mL (25 °C) slightly soluble in ammonia, benzene insoluble in diethyl ether |
| Structure | |
| body centered rhombohedral | |
| Thermochemistry | |
| 86.6 J/mol K | |
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Std molar
entropy (S |
119.2 J/mol K |
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Std enthalpy of
formation (ΔfH |
−400 kJ/mol |
| Hazards | |
| Lethal dose or concentration (LD, LC): | |
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LD50 (median dose)
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1500 mg/kg (rat, oral) |
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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 | |
Sodium cyanate (NaOCN) is a white crystalline solid that adopts a body centered rhombohedral crystal lattice structure (trigonal crystal system) at room temperature.
Sodium cyanate can be prepared by the reaction between urea and sodium carbonate.
Alternatively, it can be prepared by the oxidation of sodium cyanide. This can be done by passing oxygen through molten sodium cyanide.
One of the more recent methods of synthesis involves modifying a procedure in the production of fatty alcohols. Instead of quenching the reaction with water, ammonia is added. This allows for the ammonia to evolve into cyanate and drop out of solution as a precipitate. The precipitate is 95-97% pure with traces of bicarbonate in it. This solid is then rinsed off with water leaving sodium cyanate that has a high purity.
Sodium cyanate is an ideal nucleophile, and these nucleophilic properties make it a major contributor to the stereospecificity in certain reactions such as in the production of chiral oxazolidone.
Sodium cyanate is a useful reagent in producing asymmetrical urea derivatives that have a range of biological activity mostly in aryl isocyanate intermediates. Such intermediates as well as sodium cyanate have been used in medicine as a means of counterbalancing carcinogenic effects on the body, possibly helping people with sickle cell anemia, and blocking certain receptors for melanin which has been shown to help with obesity. In most cases the intermediates produced with sodium cyanide are used for medicinal study however, in the cases of sickle cell anemia and anti-carcinogenic research Sodium Cyanate itself was the compound of interest.
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