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Iodobenzoic acids are any of three organic compounds with the formula IC 6 H 4 COOH, consisting of a carboxylic acid group and an iodine atom bonded to a central benzene ring. They can be considered as iodinated derivatives of benzoic acid , or as carboxylated variants of iodobenzene .
In hot water (or, in Willgerodt's original preparation, steam distillation), iodosobenzene instead disproportionates to iodoxybenzene and iodobenzene: [7] 2 PhIO → PhIO 2 + PhI. 2-Iodobenzoic acid reacts with oxone [8] or a combination of potassium bromate and sulfuric acid to produce the insoluble λ 5 ‑iodane 2-iodoxybenzoic (IBX) acid. [9]
Iodobenzene is commercially available, or it can be prepared in the laboratory from aniline via the diazotization reaction. In the first step, the amine functional group is diazotized with hydrochloric acid and sodium nitrite. Potassium iodide is added to the resultant phenyldiazonium chloride, causing nitrogen gas to evolve. The product is ...
The synthesis of 2-iodobenzoic acid via the diazotization of anthranilic acid is commonly performed in university organic chemistry labs. One of its most common uses is as a precursor for the preparation of IBX and Dess–Martin periodinane , both used as mild oxidants.
PIDA can also be prepared from iodosobenzene and glacial acetic acid: [5] C 6 H 5 IO + 2 CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 + H 2 O. More recent preparations direct from iodine, acetic acid, and benzene have been reported, using either sodium perborate [6] or potassium peroxydisulfate [7] as the oxidizing agent: [8]
One method involves its conversion to the Grignard reagent, phenylmagnesium bromide. This reagent can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid. [4] Other methods involve palladium-catalyzed coupling reactions, such as the Suzuki reaction. Bromobenzene is used as a precursor in the manufacture of phencyclidine.
An example published in Organic Syntheses is the conversion of cyclobutanecarboxamide, easily synthesized from cyclobutylcarboxylic acid, to cyclobutylamine. [2] The primary amine is initially present as its trifluoroacetate salt, which can be converted to the hydrochloride salt to facilitate product purification. [1] [2]
4-iodobenzoic acid crystallization [4] X-ray crystallography of 4-iodobenzoic acid has shown that it crystallizes in the solid state as hydrogen-bonded dimers which stack perpendicular to their aromatic rings. The iodine atoms of adjacent dimers are also oriented towards each other due to van der Waals forces. [4]