2-Iodobenzoic acid

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2-Iodobenzoic acid
2-Iodobenzoic acid.svg
Names
Preferred IUPAC name
2-Iodobenzoic acid
Other names
o-Iodobenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.682 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H5IO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) Yes check.svgY
    Key: CJNZAXGUTKBIHP-UHFFFAOYSA-N Yes check.svgY
  • O=C(O)c1ccccc1I
Properties
C7H5IO2
Molar mass 248.018 g/mol
Appearancewhite solid
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

2-Iodobenzoic acid, or o-iodobenzoic acid, is an isomer of iodobenzoic acid. [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.

Contents

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 Coupling Of Anthranilic Acid.png
Diazo replacement of anthranilic acid.

See also

Related Research Articles

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Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions, shorter reaction times, higher yields, simplified workups, high chemoselectivity, tolerance of sensitive functional groups, and a long shelf life. However, use on an industrial scale is made difficult by its cost and its potentially explosive nature. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin who developed the reagent in 1983. It is based on IBX, but due to the acetate groups attached to the central iodine atom, DMP is much more reactive than IBX and is much more soluble in organic solvents.

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Benzenediazonium tetrafluoroborate is an organic compound with the formula [C6H5N2]BF4. It is a salt of a diazonium cation and tetrafluoroborate. It exists as a colourless solid that is soluble in polar solvents. It is the parent member of the aryldiazonium compounds, which are widely used in organic chemistry.

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Diphenic acid, also known as Dibenzoic acid, is an organic compound with the formula (C6H4CO2H)2. It is the most studied of several isomeric dicarboxylic acids of biphenyl. It is a white solid that can be prepared in the laboratory from anthranilic acid via the diazonium salt. It is the product of the microbial action on phenanthrene.

References

  1. "2-Iodobenzoic acid". PubChem. Retrieved 2022-11-27.