Chemical Properties
In solution, 4-Iodothioanisole shows a yellowish color due to intramolecular excitation of the cyclopentene system, while in the solid state it is orange because of free rotation around the carbon-iodine bond.It reacts with electrophiles to form carbon-iodine bonds and can be used to make cross-coupling reactions.
Uses
4-Iodothioanisole is a synthetic molecule that is used in organic chemistry as a reagent for the formation of carbon-carbon bonds. It also enhances the fluorescence of some molecules and has been used in supramolecular chemistry.
Synthesis
General procedure for the synthesis of 4-iodoanisole from 4-methylthiophenylboronic acid: KX (X = I, Br) (0.2 mmol), 4-methylthiophenylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol%), 1,10-phenanthroline (7.2 mg, 20 mol%), and DMF ( 2 mL). The reaction mixture was stirred at 80 °C or 130 °C for the reaction. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified by rapid column chromatography on silica gel to afford the target product 4-iodoanisole.
References
[1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995
[2] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1122 - 1123
[3] RSC Advances, 2015, vol. 5, # 103, p. 84910 - 84919
