orthoiodophenol

Ortho-iodophenol, or 2-iodophenol, is an organic compound in which a hydroxyl group and an iodine atom are attached to adjacent positions on a benzene ring. Its empirical formula is C6H5IO and its molecular weight is about 220 g/mol. As a substituted phenol, it behaves as a weak acid and can form phenoxide salts with bases.

It is typically prepared by electrophilic iodination of phenol under controlled conditions. The hydroxyl group directs electrophilic substitution to the ortho and para positions, with ortho isomer often forming preferentially, though mixtures are common and require purification by crystallization or chromatography.

The carbon–iodine bond in o-iodophenol is reactive in palladium- and copper-catalyzed cross-coupling reactions, making it a useful building block for the synthesis of more complex aromatic compounds. The phenolic OH can be derivatized, for example by alkylation or acylation, to give ether or ester derivatives. The iodide substituent can be substituted by nucleophiles under appropriate conditions, enabling further functionalization.

Handling requires standard precautions for organic iodides and phenols: avoid inhalation and contact with skin or eyes, and dispose of waste in accordance with local regulations.