Synthesis of acetyl cyanide (pyruvonitrile)

Preparation of acetyl cyanide (pyruvonitrile)

Preparation of acetyl cyanide

Preparation of acetyl cyanide

For the preparation of acetyl cyanide copper(I) cyanide is prepared by adding potassium cyanide in portions to copper(II) sulfate 5-hydrate with cooling and vigorous stirring. The copper cyanide is filtered off, washed thoroughly, and dried in a thermostat at 60-70° C. Acetyl bromide (1 mole) is added to copper cyanide (1 mole), which causes ebullition; no solvent is used. The mixture is heated under reflux for 1.5-2 hours, then acetyl cyanide formed is separated from copper(I) bromide by distillation. Acetyl cyanide boils at 93° C, the yield is 85-87%.

Angew. Chem. Int. Ed., Engl, 4, 583, 1965.

IUPAC Name

acetyl cyanide

InChI

InChI=1S/C3H3NO/c1-3(5)2-4/h1H3

InChI Key

QLDHWVVRQCGZLE-UHFFFAOYSA-N

Canonical SMILES

CC(=O)C#N

Depositor-Supplied Synonyms

Pyruvonitrile, Acetyl cyanide, Oxopropionitrile, 2-Oxopropionitrile, 631-57-2, Oxypropionitrile, Propanenitrile, 2-oxo-, 2-Oxopropiononitrile, Pyruvic acid nitrile, .alpha.-Oxopropionitrile, QLDHWVVRQCGZLE-UHFFFAOYSA-N, NSC91482, ACETYLCYANIDE, ACMC-20ajsw, AC1L2BUQ, AC1Q4QFW, CH3C(O)CN, UNII-ULO441649V, 269212_ALDRICH, Propanenitrile, 2-oxo-(9CI), 16000_FLUKA, CTK5B7838, ULO441649V, EINECS 211-159-2, AR-1K9435, NSC-91482, AKOS015900162, SC-51001, AI3-28761, TX-017946, InChI=1/C3H3NO/c1-3(5)2-4/h1H, I14-10193

Removed Synonyms

2-Oxopropanenitrile, CID69430, 6967-21-1

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