4-Carboxybenzaldehyde

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4-Carboxybenzaldehyde
4-Carboxybenzaldehyd Strukturformel V2.svg
Names
Preferred IUPAC name
4-Formylbenzoic acid
Systematic IUPAC name
4-Formylbenzenecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.645 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-607-4
PubChem CID
UNII
  • InChI=1S/C8H6O3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H,(H,10,11)
    Key: GOUHYARYYWKXHS-UHFFFAOYSA-N
  • InChI=1/C8H6O3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H,(H,10,11)
    Key: GOUHYARYYWKXHS-UHFFFAOYAP
  • c1cc(ccc1C=O)C(=O)O
Properties
C8H6O3
Molar mass 150.133 g·mol−1
Appearancewhite solid
Melting point 245 °C (473 °F; 518 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Carboxybenzaldehyde (CBA) is an organic compound with the formula OCHC6H4CO2H. It consists of a benzene ring substituted with both an aldehyde and a carboxylic acid, with these functional groups on opposite corners of the ring. This compound is formed in 0.5% yield as a byproduct in the production terephthalic acid from p-xylene. Since approximately 40,000,000 tons of terephthalic acid are produced per year, CBA is a relatively large scale industrial chemical. [1]

See also

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Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

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<span class="mw-page-title-main">2-Carboxybenzaldehyde</span> Chemical compound

2-Carboxybenzaldehyde is a chemical compound. It consists of a benzene ring, with an aldehyde and a carboxylic acid as substituents that are ortho to each other. The compound exhibits ring–chain tautomerism: the two substituents can react with each other to form 3-hydroxyphthalide, a cyclic lactol. This lactol reacts readily with Grignard reagents, forming alkyl- and aryl-substituted phthalides. Other benzo-fused heterocyclic compounds can be derived from 2-carboxybenzaldehyde, including isoindolinones and phthalazinones, with a variety of pharmacological properties, such as the antihistamine azelastine.

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References

  1. Barnicki, Scott D. (2012). "Synthetic Organic Chemicals". In Kent, James A. (ed.). Handbook of Industrial Chemistry and Biotechnology. Boston, MA: Springer US. pp. 307–389. doi:10.1007/978-1-4614-4259-2_10. ISBN   978-1-4614-4258-5.