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Sodium cyanide, granules, 98%, Thermo Scientific Chemicals
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Chemical Identifiers
CAS143-33-9
IUPAC Namesodium iminomethanide
Molecular FormulaCNNa
InChI KeyMNWBNISUBARLIT-UHFFFAOYSA-N
SMILES[Na+].[C-]#N
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Specifications
Specification Sheet
Specification SheetAppearance (Color)White to pale cream
FormGranules
Assay from Supplier's CofA≥97.5%
Sodium cyanide is used as a starting material for the preparation of Reissert compounds and cyanogen bromide, cyanuric chloride and cyanogen chloride. It acts as a catalyst for the aminolysis of esters to primary amides. Furthermore, it is used for fumigation, electroplating, extracting gold and silver in mining industry. In organic synthesis, it is involved in the cyanation reaction of alkyl halides under phase transfer conditions.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Sodium cyanide is used as a starting material for the preparation of Reissert compounds and cyanogen bromide, cyanuric chloride and cyanogen chloride. It acts as a catalyst for the aminolysis of esters to primary amides. Furthermore, it is used for fumigation, electroplating, extracting gold and silver in mining industry. In organic synthesis, it is involved in the cyanation reaction of alkyl halides under phase transfer conditions.
Solubility
Soluble in water, ammonia, methanol and ethanol. Slightly soluble in dimethylformamide. Insoluble in dimethylsulphoxide.
Notes
Hygroscopic. Do not store near acids. Incompatible with strong oxidizing agents and carbon dioxide.
Sodium cyanide is used as a starting material for the preparation of Reissert compounds and cyanogen bromide, cyanuric chloride and cyanogen chloride. It acts as a catalyst for the aminolysis of esters to primary amides. Furthermore, it is used for fumigation, electroplating, extracting gold and silver in mining industry. In organic synthesis, it is involved in the cyanation reaction of alkyl halides under phase transfer conditions.
Solubility
Soluble in water, ammonia, methanol and ethanol. Slightly soluble in dimethylformamide. Insoluble in dimethylsulphoxide.
Notes
Hygroscopic. Do not store near acids. Incompatible with strong oxidizing agents and carbon dioxide.
WARNING: Reproductive Harm - www.P65Warnings.ca.gov
RUO – Research Use Only
General References:
- Cyanations of alkyl halides are often carried out most conveniently under phase-transfer conditions: Synth. Commun., 6, 193 (1976); see: E. V. Dehmlow and S. S. Dehmlow, Phase-Transfer Catalysis, 3rd ed., VCH, N.Y. (1993), for further extensive examples. DMSO is also a good solvent for these reactions: J. Org. Chem., 25, 257, 877 (1960).
- For formation of Reissert compounds, see Quinoline, A11545.
- Mild catalyst for the aminolysis of esters to primary amides: J. Org. Chem., 52, 2033 (1987).
- For generation of cyanogen bromide by reaction with bromine, see: Org. Synth. Coll ., 7, 435 (1990).
- See also Potassium cyanide, L13273.
- Murahashi, S. I.; Nakae, T.; Terai, H.; Komiya, N. Ruthenium-Catalyzed Oxidative Cyanation of Tertiary Amines with Molecular Oxygen or Hydrogen Peroxide and Sodium Cyanide: sp3 C-H Bond Activation and Carbon- Carbon Bond Formation. J. Am. Chem. Soc. 2008, 130 (33), 11005-11012.
- Singhal, S.; Jain, S. L.; Sain, B. An efficient aerobic oxidative cyanation of tertiary amines with sodium cyanide using vanadium based systems as catalysts. Chem. Commun. 2009, 17, 2371-2372.