2-Iodobenzoic acid

2-Iodobenzoic acid

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Names
IUPAC name 2-Iodobenzoic acid
Other names o-Iodobenzoic acid
Identifiers
CAS Number	88-67-5 Y
ChEBI	CHEBI:287979 Y
ChEMBL	ChEMBL112424 Y
ChemSpider	6675 Y
Jmol 3D model	Interactive image
PubChem	6941
InChI InChI=1S/C7H5IO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) Y Key: CJNZAXGUTKBIHP-UHFFFAOYSA-N Y
SMILES O=C(O)c1ccccc1I
Properties
Chemical formula	C7H5IO2
Molar mass	248.018
Density	2.25 g/cm3
Melting point	162 °C (324 °F; 435 K)
Vapor pressure	{{{value}}}
Vapor pressure	{{{value}}}
Except where otherwise noted, 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 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

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.