Sodium cyanate

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Sodium cyanate
Sodium Cyanate.svg
Identifiers
917-61-3 YesY
ChEBI CHEBI:1159669
ChemSpider 12922
EC Number 213-030-6
Jmol 3D model Interactive image
MeSH C009281
PubChem 517096
  • InChI=1S/CHNO.Na/c2-1-3;/h3H;/q;+1/p-1
    Key: ZVCDLGYNFYZZOK-UHFFFAOYSA-M
  • C(#N)[O-].[Na+]
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
119.2 J/mol K
−400 kJ/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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.[1]

Preparation

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.

2NaCN + O2 → 2 NaOCN

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.[2]

Chemical Uses

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.[3]

Medical Applications

Sodium cyanate is a useful reagent in producing asymmetrical urea that have a range of biological activity mostly in aryl isocyanate intermediates.[4] Such intermediates as well as sodium cyanate have been used in medicine as a means of counterbalancing carcinogenic effects on the body,[5] possibly helping people with sickle cell anemia,[6] and blocking certain receptors for melanin which has been shown to help with obesity.[7] 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. Lua error in package.lua at line 80: module 'strict' not found.

See also

References

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  1. ↑ 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.
  2. ↑ Kamlet, Jonas "Patent US2563044 A - Concurrent manufacture of sodium cyanate and fatty alcohols." Google Books. N.p., n.d. Web. 09 Nov. 2014.
  3. ↑ Expedient Synthesis of Chiral Oxazolidinone Scaffolds via Rhodium-Catalyzed Asymmetric Ring-Opening with Sodium Cyanate Gavin Chit Tsui, Nina M. Ninnemann, Akihito Hosotani, and Mark Lautens Organic Letters 2013 15 (5), 1064-1067
  4. ↑ see 7.)
  5. ↑ Inhibition of Carcinogen-induced Neoplasia by Sodium Cyanate, tert-Butyl Isocyanate, and Benzyl Isothiocyanate Administered Subsequent to Carcinogen Exposure Lee W. Wattenberg Cancer Res August 1981 41:2991-2994
  6. ↑ STUDIES WITH INTRAVENOUS SODIUM CYANATE IN PATIENTS WITH SICKLE CELL ANEMIA Charles M. Peterson, Yang S. Lu, John T. Herbert, Anthony Cerami, and Peter N. Gillette J Pharmacol Exp Ther June 1974 189:577-584; published online June 1, 1974,
  7. ↑ Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas Ekaterina V. Vinogradova, Brett P. Fors, and Stephen L. Buchwald Journal of the American Chemical Society 2012 134 (27), 11132-11135
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