Synthesis of iodoform (triiodomethane)

Preparation of iodoform

Preparation of iodoform

Preparation of iodoform

To a solution of 30 g (0.19 mol) of potassium iodide in 100 ml of water, placed in 1.5 liter round-bottomed flask equipped with a stirrer, 10 ml (8 g or 0.13 mol) of acetone and with stirring is poured. In small portions, 300 ml of 5% aqueous sodium hypochlorite solution is slowly dropwise added. At the end of the reaction a yellow precipitate of iodoform forms. It usually occurs after the addition of a little more than 300 mL of sodium hypochlorite. The stirrer was turned off and the reaction mixture allowed to stand 0.5 hours. The crystals of iodoform were filtered on a Buchner funnel and washed thoroughly with water. The dried iodoform recrystallized from ethanol (300 ml) to give it in the form of yellow crystals (with melting point 119 °) and a characteristic odor. Yield, 17.5 g (35% of theory). Iodoform dissolved in methanol and ethanol, acetone, ether and chloroform; insoluble in water, distilled with steam. Under the influence of air and light iodoform gradually decomposes.

Other methods of obtaining iodoform get action on acetone in the presence of potassium iodide, as well as action on ethyl alcohol, isopropyl alcohol or acetone potassium iodide and oxidizing agents such as hypochlorites or dichloramines in alkaline solution. there also is an electrochemical method for preparation of iodoform by electrolysis of potassium iodide.

Препаративная органическая химия, Вульфсон Н.С., 184, 1959 (Preparative organic chemistry, Wolfson N. S., 184, 1959)

IUPAC Name

iodoform

InChI

InChI=1S/CHI3/c2-1(3)4/h1H

InChI Key

OKJPEAGHQZHRQV-UHFFFAOYSA-N

Canonical SMILES

C(I)(I)I

MeSH Synonyms

iodoform, tri-iodomethane

Depositor-Supplied Synonyms

IODOFORM, Triiodomethane, Methane, triiodo-, 75-47-8, Carbon triiodide, Jodoform, Trijodmethane, Dezinfekt V, NCI-C04568, Jodoform [Czech], Trijodmethane [Czech], CCRIS 346, UNII-KXI2J76489, CHEBI:37758, HSDB 4099, OKJPEAGHQZHRQV-UHFFFAOYSA-N, EINECS 200-874-5, NSC 26251, NCGC00091389-01, AI3-52396, DSSTox_CID_743, DSSTox_RID_75765, DSSTox_GSID_20743, CAS-75-47-8, Iodoform (TN), Iodoform [JAN], tris(iodanyl)methane, ACMC-20akq1, WLN: IYII, AC1L1MDX, CHI3, Iodoform (JP16/USP), KSC377O0R, 109452_ALDRICH, CHEMBL1451116, 57980_FLUKA, CTK2H7708, MolPort-001-783-761, KXI2J76489, LTBB002749, EBD19519, NSC26251, Tox21_111124, Tox21_202389, Tox21_302774, NSC-26251, AKOS009031506, LS-1666, RTR-024271, NCGC00091389-02, NCGC00091389-03, NCGC00256394-01, NCGC00259938-01, AN-23858, K290, SC-16447, AB1001960, TR-024271, FT-0627266, C13383, D01910, A838427, I14-7271, 3B3-033904

Removed Synonyms

tri-iodomethane, CID6374, C010473

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