2-Iodobenzoic acid

2-Iodobenzoic acid
Names
	IUPAC name 2-Iodobenzoic acid
	Other names o-Iodobenzoic acid
Identifiers
CAS Number	88-67-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:287979 ;
ChEMBL	ChEMBL112424 ;
ChemSpider	6675 ;
ECHA InfoCard	100.001.682
PubChem CID	6941;
UNII	7Q00V80J7Q ;
CompTox Dashboard (EPA)	DTXSID6058976 ;
	InChI InChI=1S/C7H5IO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) Key: CJNZAXGUTKBIHP-UHFFFAOYSA-N ;
	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)
	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 highly nucleophilic I⁻ anion.

Diazo replacement of anthranilic acid.

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

References

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