Harman Patil (Editor)

2 Iodobenzoic acid

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Formula  C7H5IO2
Density  2.25 g/cm³
2-Iodobenzoic acid 2Iodobenzoic acid8867513CNMR

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.

2-Iodobenzoic acid 2Iodobenzoic acid88675IR2

Synthesis

2-Iodobenzoic acid 2Iodobenzoic acid88675IR1

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.

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

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References

2-Iodobenzoic acid Wikipedia


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