Synthesis of cyanogen iodide

Preparation of cyanogen iodide

Cyanogen iodide, similarly to cyanogen bromide and cyanogen chloride, is prepared by the action of iodine on sodium cyanide.

Preparation of cyanogen iodide

Preparation of cyanogen iodide

To the round bottom flask fitted with dropping funnel containing 100 ml 5% aqueous solution of sodium cyanide, stirrer, inlet and outlet tubes for gas 12 g iodine and 20 g water are placed. The reaction mixture is stirred and 50 ml of the sodium cyanide solution are added slowly drop-wise. The NaI formed in the reaction dissolves the iodine and the liquid in the flask is continuously decolorized. When the 50 ml sodium cyanide solution have been added, a slow current of chlorine is passed into the flask, and while continuing to stir the liquid the other 50 ml cyanide solution are added from the dropping-funnel at such a rate that there is always an excess of iodine present. The current of chlorine is then stopped and a little more sodium cyanide is added. Cyanogen iodide is then extracted with ether, the ethereal extract dried over calcium chloride and filtered. The ether distilled off and a crystalline residue of cyanogen iodide collected yielding 80-85% of theoretical. Cyanogen iodide forms white crystals which gradually decompose. It melts at 140-146° C. Cyanogen iodide dissolves slightly in cold water, soluble in alcohol and ether.

The war gases chemistry and analysis, by M. Sartory, 193-194, 1939.

IUPAC Name

carbononitridic iodide

InChI

InChI=1S/CIN/c2-1-3

InChI Key

WPBXOELOQKLBDF-UHFFFAOYSA-N

Canonical SMILES

C(#N)I

Depositor-Supplied Synonyms

CYANOGEN IODIDE, Iodine cyanide, carbononitridic iodide, Iodocyanide, Jodcyan, cyanic iodide, Iodine cyanide (I(CN)), Iodine monocyanide, Cyanogen monoiodide, 506-78-5, HSDB 6328, EINECS 208-053-3, BRN 1697297, AI3-28744, QMbDkDfp@, CYANOGENIODIDE, AC1L1VAD, AC1Q4P4B, UNII-81ESV254UF, 81ESV254UF, WPBXOELOQKLBDF-UHFFFAOYSA-N, LS-84142, FT-0654480, 4-03-00-00093 (Beilstein Handbook Reference), A828244, S14-1188

Removed Synonyms

CID10478, ICN

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