Description
2-iodobenzoic acid and its derivatives are important pharmaceutical and chemical raw materials, which are necessary for the synthesis of various high-iodine reagents. It is commonly used as a precursor for the synthesis of 2-Iodoxybenzoic acid (IBX) and Dess-Martin peridinane, which are used as mild oxidants. It is also used in Suziki reaction.
Chemical Properties
white crystal powder. Soluble in alcohol and ether, insoluble in water.
Uses
Reagent for detection of sulfhydryl groups in proteins. 2-Iodobenzoic acid acts as a precursor in the preparation of 2-Iodoxybenzoic acid (IBX) and Dess-Martin periodinane, which finds application as an oxidizing agent in synthetic chemistry. It is also used in Suzuki reaction.
Preparation
2-Iodobenzoic acid is obtained from Anthranilic acid by diazotization and substitution. Diazotization of Anthranilic acid with sodium nitrite in the presence of sulfuric acid, control the temperature below 10℃, filter the diazotization solution, add the mixture of potassium iodide and sulfuric acid, stir for 10min after addition, and boil. Filter, wash with sodium thiosulfate solution, 2-Iodobenzoic acid can be recrystallized from water.
Definition
ChEBI: An iodobenzoic acid with a single iodo substituent placed at the 2-position.
Synthesis Reference(s)
Journal of the American Chemical Society, 93, p. 4841, 1971
DOI: 10.1021/ja00748a029
Purification Methods
Crystallise the acid repeatedly from water and EtOH. Sublime it under vacuum at 100o. [Beilstein 9 IV 1030.]
