Sodium cyanate
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| Identifiers | |
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CAS Number |
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3D model (JSmol) |
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Beilstein Reference | 3655041 |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.011.846  |
| EC Number |
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| MeSH | C009281 |
PubChem CID |
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| UNII |
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CompTox Dashboard (EPA) |
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InChI
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| Properties | |
Chemical formula | 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) |
Solubility in water | 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 | |
Heat capacity (C) | 86.6 J/mol K |
Std molar entropy (S⦵298) | 119.2 J/mol K |
Std enthalpy of formation (ΔfH⦵298) | −400 kJ/mol |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H412 | |
| P264, P270, P273, P301+P312, P330, P501 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 1500 mg/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references | |
Chemical compound
Sodium cyanate is the inorganic compound with the formula NaOCN. A white solid, it is the sodium salt of the cyanate anion.
Structure
The anion is described by two resonance structures: N≡C−O− and −N=C=O
The salt adopts a body centered rhombohedral crystal lattice structure (trigonal crystal system) at room temperature.[1]
Preparation
Sodium cyanate is prepared industrially by the reaction of urea with sodium carbonate at elevated temperature.
- 2OC(NH2)2 + Na2CO3 → 2Na(NCO) + CO2 + 2NH3 + H2O
Sodium allophanate is observed as an intermediate:[2]
- H2NC(O)NHCO2Na → NaOCN + NH3 + CO2
It can also be prepared in the laboratory by oxidation of a cyanide in aqueous solution by a mild oxidizing agent such as lead oxide.[3]
Uses and reactions
The main use of sodium cyanate is for steel hardening.[2]
Sodium cyanate is used to produce cyanic acid, often in situ:
- NaOCN + HCl → HOCN + NaCl
This approach is exploited for condensation with amines to give unsymmetrical ureas:
- HOCN + RNH2 → RNHC(O)NH2
Such urea derivatives have a range of biological activity.[4]
See also
References
- ^ Waddington, T.C. "Journal of the Chemical Society (Resumed)." 499. Lattice Parameters and Infrared Spectra of Some Inorganic Cyanates - (RSC Publishing). N.p., n.d. Web. 09 Nov. 2014.
- ^ a b Schalke, Peter M. (2006). "Cyanates, Inorganic Salts". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_157.pub2. ISBN 3527306730.
- ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. p. 324. ISBN 978-0-08-037941-8.
- ^ Vinogradova, Ekaterina V.; Fors, Brett P.; Buchwald, Stephen L. (11 July 2012). "Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas". Journal of the American Chemical Society. 134 (27): 11132–11135. doi:10.1021/ja305212v. PMC 3472423. PMID 22716197.
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| Halides | |
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| Chalcogenides | |
| Pnictogenides |
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| Oxyhalides | |
| Oxychalcogenides |
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| Oxypnictogenides |
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| Others |
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- CH3ONa
- C2H5ONa
- HCOONa
- C2H5COONa
- C3H7COONa
- Na2C4H4O6
- C4H5NaO6
- NaCH3COO
- NaC6H5CO2
- NaC6H4(OH)CO2
- NaC12H23O2
- NaC10H8
- Na2[Fe[CN5]NO]
- C6H16AlNaO4
- NaC6H7O6
- C5H8NO4Na
- C6H5Na
- C4H9Na
- NaC5H5
- C15H31COONa
- C17H33COONa
- C18H35O2Na
- C164H256O68S2Na2
