2-Iodobenzoic acid

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2-Iodobenzoic acid
2-Iodobenzoic acid.svg
Names
IUPAC name
2-Iodobenzoic acid
Other names
o-Iodobenzoic acid
Identifiers
88-67-5 YesY
ChEBI CHEBI:287979 YesY
ChEMBL ChEMBL112424 YesY
ChemSpider 6675 YesY
Jmol-3D images Image
PubChem 6941
Properties
C7H5IO2
Molar mass 248.018
Melting point 162 °C (324 °F; 435 K)
Except where noted otherwise, data is 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 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.

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]