Synthesis of methyl iodide

Preparation of methyl iodide

Preparation of methyl iodide from methanol and iodine

Preparation of methyl iodide from methanol and iodine

Preparation of methyl iodide from methanol and iodine

To a round bottom flask fitted with a reflux condenser 180 grams of methanol and 50 grams of red phosphorus are placed. 500 grams of iodine are gradually added to the reaction mixture. A considerable evolution of heat occurs and when the iodine has been added the reaction flask is left attached to the condenser over night. The next day crude methyl iodide is distilled, the distillate is washed in a separating funnel with the dilute solution of sodium hydroxide in order to remove iodine and hydriodic acid. If sufficient amount of sodium hydroxide is used the lower layer of methyl iodide will be colorless. Methyl iodide is separated and dried with calcium chloride, and finally purified by distillation. Yield of methyl iodide is 450 grams. Ethyl iodide and the other alkyl iodides are prepared in precisely the same manner.

Preparation of methyl iodide from dimethyl sulfate and potassium iodide

Preparation of methyl iodide from dimethyl sulfate and potassium iodide

Preparation of methyl iodide from dimethyl sulfate and potassium iodide

To a solution of 100 grams potassium iodide in 100 ml water 80 grams of dimethyl sulfate under gentle heat are dropwise added. The obtained pure methyl iodide is distilled nearly the theoretical amount.

Methyl iodide is a colorless, highly refractive liquid; Boiling point 45° C, d= 2.27 g/cm3 at 15° C.

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

IUPAC Name

iodomethane

InChI

InChI=1S/CH3I/c1-2/h1H3

InChI Key

INQOMBQAUSQDDS-UHFFFAOYSA-N

Canonical SMILES

CI

MeSH Synonyms

iodomethane, iodomethane-D3, methyl iodide, methyl iodide, 11C-labeled, methyl iodide, 131I-labeled, methyl iodide, 132I-labeled, methyl iodide, 13C-labeled, methyl iodide, 14C-labeled, methyl iodide, 2H-labeled

Depositor-Supplied Synonyms

IODOMETHANE, Methyl iodide, Methane, iodo-, Monoiodomethane, Methyljodid, 74-88-4, Jod-methan, Joodmethaan, Methyliodide, Methyljodide, Iodometano, Methyl iodine, Metylu jodek, Iodure de methyle, Halon 10001, Monoioduro di metile, iodo-methane, CH3I, RCRA waste number U138, Joodmethaan [Dutch], Iodometano [Italian], Methyljodid [German], Methyljodide [Dutch], Jod-methan [German], Metylu jodek [Polish], NSC 9366, UNII-DAT010ZJSR, RCRA waste no. U138, Iodure de methyle [French], CCRIS 395, Monoioduro di metile [Italian], CHEBI:39282, HSDB 1336, INQOMBQAUSQDDS-UHFFFAOYSA-N, Iodomethane solution, EINECS 200-819-5, UN2644, iodomethan, iodornethane, methyliodine, Methyliodid, Monoiodmethan, Iodmethan, iodo methane, metyl iodide, Methyl-iodide, meth-yl iodide, 1-iodomethane, RFDEYF@, DAT010ZJSR, AC1L1MA9, AC1Q38HY, WLN: I1, 456756_ALDRICH, CHEMBL115849, I8507_SIAL, CTK2H8218, InChI=1/CH3I/c1-2/h1H, NSC9366, MolPort-000-156-457, LTBB002606, 289566_SIAL, 456756_SIAL, ACT10179, NSC-9366, ANW-56407, BBL034228, Methyl iodide [UN2644] [Poison], STL281179, AKOS009031541, Methyl iodide [UN2644] [Poison], MCULE-1718786667, UN 2644, AN-41969, BP-11384, LS-90046, TR-024159, FT-0628742, FT-0628743, I0060, C18448, 3B4-2644, I14-5819, I14-14230, 147937-07-3

Removed Synonyms

Iodomethane-d3, 5-Iodoisatin, methyl iodide, 2H-labeled, methyl iodide, 11C-labeled, methyl iodide, 13C-labeled, methyl iodide, 14C-labeled, methyl iodide, 131I-labeled, methyl iodide, 132I-labeled, CHEMBL3228330, CID6328, C014055, MEI, 101398-43-0

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