Regioselective iodination of aromatic compounds with potassium iodide in the presence of benzyltriphenylphosphonium perchlorate was written by Albadi, Jalal;Abedini, Masoumeh;Iravani, Nasir. And the article was included in Chinese Chemical Letters in 2012.SDS of cas: 75581-11-2 This article mentions the following:
A simple and efficient method for the selective iodination of various aromatic compounds by using potassium iodide in the presence of benzyltriphenylphosphonium perchlorate, is reported. This method provides several advantages such as good selectivity between ortho and para positions of aromatic compounds and high yields of the products. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).
4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).SDS of cas: 75581-11-2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem