2-Iodobenzoic acid

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2-Iodobenzoic acid
2-Iodobenzoic acid.svg
Identifiers
CAS number 88-67-5 YesY
PubChem 6941
ChemSpider 6675 YesY
ChEBI CHEBI:287979 YesY
ChEMBL CHEMBL112424 YesY
Jmol-3D images Image 1
Properties
Molecular formula C7H5IO2
Molar mass 248.018
Melting point 162 °C (324 °F; 435 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

2-Iodobenzoic acid, or o-iodobenzoic acid, is an organic compound with the formula IC6H4COOH. The synthesis of 2-iodobenzoic acid via the diazotization of anthranilic acid is a common 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.

Synthesis[edit]

2-Iodobenzoic acid can be synthesized via a Sandmeyer reaction consisting of the diazotization of anthranilic acid followed by a diazo replacement. First anthranilic acid is treated with nitrous acid in order to convert the amino group into the diazo group. The diazo group is ejected, yielding a carbocation which is then attacked by the highly nucleophilic I- anion.

Diazo replacement of anthranilic acid.

The nitrous acid is usually generated in situ from sodium nitrite.

References[edit]