2,4,6-Trimethyliodobenzene

Chemical properties

yellow crystalline low melting solid

The Uses of 2,4,6-Trimethyliodobenzene

suzuki reaction

The Uses of 2,4,6-Trimethyliodobenzene

Iodomesitylene can be used as a good catalyst for living radical polymerization due to its good molecular weight distribution.

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 2427, 1969 DOI: 10.1017/S0009838800024678

Hazard

May cause eye, skin, and respiratory tract irritation. Light sensitive.

Health effects

Eye: May cause eye irritation.
Skin: May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion: May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.

Synthesis

The synthesis of 2,4,6-Trimethyliodobenzene is as follows:
A 10 mL glass flask equipped with a magnetic stir bar wascharged with a methyl ketone (1 mmol) and dissolved in MeCN (2 mL). To thermostat solution NH4NO3 (10-25 mol%), I2 (50 mol%) and H2SO4 (aqueous 96% solution, 10-20 mol%) were added and the flask was furtherequipped with a balloon filled with air (1 L) and magnetically stirred at 60 C.The consumption of starting material was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, diluted withEtOAc (10 mL), and insoluble material identified as ammonium sulfate filtered off. The filtrate neutralized with NaHCO3 (aqueous 10% solution, 2 mL)and Na2S2O3 (aqueous 10% solution, 2 mL) and phase was separated. The waterphase was washed with EtOAc additionally two times (2 5 mL). The combined organic phase was dried over anhydrous Na2SO4 and the solvent distilled under reduced pressure. The crude product obtained was analyzed by 1H NMR. Finally, the crude product was purified using column chromatography (SiO2, n-hexane/CH2Cl2 elution) and preparative thin layer chromatography to afford purematerial.

Storage

Store in a cool, dry place. Store in a tightly closed container. Store protected from light.