The direct iodination of polyalkylbenzenes bearing bulky groups was written by Suzuki, Hitomi;Nakamura, Kiyomi;Goto, Ryozo. And the article was included in Bulletin of the Chemical Society of Japan in 1966.COA of Formula: C10H12I2 This article mentions the following:
A number of polyalkylbenzenes, bearing bulky substituents, afforded mono-iodo derivatives in high yield when treated with iodine-HIO4. HIO4 proved to be the most effective of several oxidizing agents examnd.: Ag2SO4, AgClO4, HgO, K2S2O8, HIO3, and ο-IC6H4OMe. The reaction also proceded smoothly to yield mono- and diiodo derivatives of some polymethylbenzenes, but tri- and tetraiodination of xylene was difficult to effect. In a typical preparation a mixture of 5.40 g. 5-tert-Bu-1,3-Me2C6H3, 1.54 g. HIO4.2H2O, 3.39 g. iodine, and 20 ml. 10:2:0.3 AcOH-H2O-H2SO4 was stirred 4 hrs. at 60-5°. The mixture was cooled and the solid product was crystallized from petr. ether to give 8.7 g. 4-tert-Bu-2,6-Me2C6H2I, m. 59-60°. The iodine atom was assumed to enter the ring para to the tert-Bu group. A similar procedure afforded the following compounds in good yield (compound, reaction time, reaction temperature, m.p., and b.p./mm. given): 5-tert-Bu-2,3-Me2C6H2I, 6-7 hrs., 60-5°,–, 146-7°/14; 6-tert-Bu-2,3,4-Me3C6HI, 6-7 hrs., 60-5°, 74-5°,–; 2,3,5,6-iso-Pr4C6HI, 30 hrs., 75-80°, 161-3°,–; 2,5-tert-Bu2C6H3I, ∼30 hrs., 75-80°,–, 156-7°/13-14; 4,5-I2-1,2-Me2C6H2, 3-4 hrs., 70°, 93-4°,–; 2,5-I2-1,4-Me2C6H2, 3-4 hrs., 70°, 104-5°,–; diiodoprehnitene, 1.5 hrs., 70°, 190-1°,–; diiododurene, 1.5 hrs., 70°, 140-1°,–. Where necessary, compounds were purified by chromatography over alumina and structures were verified by ir spectral examination In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1COA of Formula: C10H12I2).
1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.COA of Formula: C10H12I2
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com