Synthesis of methylene iodide

Preparation of methylene iodide

Preparation of methylene iodide from iodoform with hydriodic acid

Preparation of methylene iodide by reacting iodoform with hydriodic acid

Preparation of methylene iodide by reacting iodoform with hydriodic acid

To a 1-liter round bottom flask  fitted with a reflux condenser, 120 ml of concentrated (57%) hydriodic acid and 50 grams iodoform are added. The reaction mixture is heated and the evaluation of hydrogen iodide begins. Then to the reaction mixture, in very small pieces, 1.5 grams of white phosphorus are added. Once after prolonged boiling the liquid no longer turns brown, it is again charged with 100 g iodoform and 3 g of white phosphorus. For the completion of the reaction in total 450 grams of iodoform and 13.5 grams of white phosphorus are added. After cooling, the reaction mixture is poured in water, the heavy oily layer is separated, washed and dried with solid potassium carbonate. Final purification is achieved by distillation under reduced pressure.

Handbuch der präparativen chemie, by Ludwig Vanilo, 1922, 34.

Preparation of methylene iodide from iodoform and sodium arsenite

By refluxing iodoform with an aqueous solution of sodium arsenite and sodium hydroxide gives a very smooth reaction with 90% yield of pure methylene iodide.

Preparation of methylene iodide by reacting iodoform with sodium arsenite

Preparation of methylene iodide by reacting iodoform with sodium arsenite

To a round bottom flask fitted with a mechanical stirrer, a reflux condenser and a dropping funnel 1000 grams of iodoform are placed. To the flask with the iodiform a solution of 500 ml of sodium arsenite from a dropping funnel are added. The solution of sodium arsenite is prepared by reacting 274 grams of arsenic trioxide with 532 grams of sodium hydroxide in 2600 ml of water. The reaction mixture is started to heat until the reaction begins. To complete the reaction, the mixture is refluxed for one hour. Then the warm mixture (40-60° C) is filtered. The methylene iodide is separated, dried with calcium chloride and purified by distillation in vacuum at 106-107° C/70 mm. The yield of crude methylene iodide is 610 grams or 90 % theory. Pure methylene iodide may be obtained by redistillation of crude product.

Organic chemical reagents, R. Adams, 29, 1919

IUPAC Name

diiodomethane

InChI

InChI=1S/CH2I2/c2-1-3/h1H2

InChI Key

NZZFYRREKKOMAT-UHFFFAOYSA-N

Canonical SMILES

C(I)I

MeSH Synonyms

diiodoethane, diiodomethane, methylene diiodide, methylene iodide, methylene iodide, 14C-labeled

Depositor-Supplied Synonyms

DIIODOMETHANE, Methylene iodide, Methane, diiodo-, 75-11-6, Methylene diiodide, MI-Gee, Dijodmethan, Methylenjodid, diiodo-methane, Dijodmethan [Czech], Methylenjodid [Czech], NSC 35804, NZZFYRREKKOMAT-UHFFFAOYSA-N, EINECS 200-841-5, Di-iodomethane; Methylene iodide, methvleneiodide, methyleneiodide, Methyl diiodide, Mi-gee brand, bis(iodanyl)methane, QMABlZqIh@, ACMC-1BGAZ, AC1L1MBR, SCHEMBL185, WLN: I1I, CH2I2, KSC377G1H, CCRIS 8551, UNII-3J731705OX, CTK2H7313, MolPort-000-150-264, BB_SC-6852, 158429_SIAL, NSC35804, STR03006, ANW-13590, BBL011419, KM1670, NSC-35804, STL146526, AKOS002664705, 3J731705OX, MCULE-8023612181, RTR-024206, AK121968, AN-23838, BP-21047, FS000809, K284, KB-76592, LS-90036, Diiodomethane, stabilized with Copper chip, ST2406799, TR-024206, D0610, FT-0628875, A838327, I14-0204, 3B3-033693, 103883-81-4

Removed Synonyms

CID6346

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