2-Iodobenzoic acid

2-Iodobenzoic acid, or o-iodobenzoic acid, is an organic compound with the formula IC6H4COOH.[1] 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-Iodobenzoic acid
Names
Preferred IUPAC name
2-Iodobenzoic acid
Other names
o-Iodobenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.682
UNII
  • InChI=1S/C7H5IO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) checkY
    Key: CJNZAXGUTKBIHP-UHFFFAOYSA-N checkY
  • O=C(O)c1ccccc1I
Properties
C7H5IO2
Molar mass 248.018 g/mol
Density 2.25 g/cm3
Melting point 162 °C (324 °F; 435 K)
Related compounds
Related compounds
 4-Iodobenzoic acid
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

Synthesis

2-Iodobenzoic acid can be synthesized by a Sandmeyer reaction: the diazotization of anthranilic acid followed by a reaction with iodide.

Diazo replacement of anthranilic acid.
Diazo replacement of anthranilic acid.

See also

References
  1. PubChem. "2-Iodobenzoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-27.
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