Sodium cyanate

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Sodium cyanate
Sodium Cyanate.svg
Identifiers
  • 917-61-3 checkY
3D model (JSmol)
3655041
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.011.846 Edit this at Wikidata
EC Number
  • 213-030-6
MeSH C009281
UNII
  • 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
Std enthalpy of
formation (ΔfH⦵298)
 −400 kJ/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Signal word
 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

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 is prepared industrially by the reaction of urea with sodium carbonate at elevated temperature.

2OC(NH2)2 + Na2CO3 → 2Na(NCO) + CO2 + 2NH3 + H2O

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.[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 derivatives 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.[4]

See also[]

References[]

  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. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. p. 324. ISBN 978-0-08-037941-8.
  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. ^ a b 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.
  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. Journal of Pharmacological Experimental Therapy June. 1974 189:577-584; published online June 1, 1974,


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