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Iodobenzoic acid isomers Common name and systematic name 2-Iodobenzoic acid [1] 3-Iodobenzoic acid [2] 4-Iodobenzoic acid [3] Structure Molecular formula: C 7 H 5 IO 2 (IC 6 H 4 COOH) Molar mass: 248.018 g/mol Appearance white solid white solid white solid CAS number [88-67-5] [618-51-9] [619-58-9] Properties Density and phase: 2.25 g/ml, solid ...
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]
It may be prepared via the Schiemann reaction, in which a 4-aminobenzoic acid, protected as the ethyl ester, is diazotised and then fluoride introduced using tetrafluoroborate. Hydrolysis of the ester converts it back to the free acid. [2] 4-Fluorobenzoic acid has been observed to form by the aerobic biotransformation of 4-fluorocinnamic acid. [3]
[1] 11,000 pounds (5,000 kg) of bentranil was used in the US in 1974. [2] Bentranil has excellent selectivity on germinaceous crops, potatoes and soybeans, but was never commercialised due to the high doses needed to control broadleaf weeds. [3] Bentranil is synthesised from 2-iodobenzoic acid and benzonitrile. [1]
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 separated by steam distillation. [2] Alternatively, it can be produced by refluxing iodine and nitric acid with benzene. [3]
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.
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] IBX acid is unstable and explosive, but acetylation tempers it to the stabler Dess-Martin periodinane. [10]
2-Fluorobenzoic acid is an aromatic organic compound with the formula FC 6 H 4 CO 2 H. It is one of three isomeric fluorobenzoic acids. Its conjugate base is 2-fluorobenzoate. The compound is an irritant. Its metabolism has been studied extensively in the field of microbiology.