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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.
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.
Hazard Statements: H290-H300-H310-H330-H372
May be corrosive to metals. Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes damage to organs through prolonged or repeated exposure.
Precautionary Statements: P301+P310a-P304+P340-P320-P330-P405-P501a
IF SWALLOWED: Immediately call a POISON CENTER/doctor IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.