Peroxybenzoic acid

Peroxybenzoic acid is an organic compound with the formula C6H5CO3H. It is the simplest aryl peroxy acid. It may be synthesized from benzoic acid and hydrogen peroxide,[3] or by the treatment of benzoyl peroxide with sodium methoxide, followed by acidification.[4]

Peroxybenzoic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Benzenecarboperoxoic acid[1]
Systematic IUPAC name
Oxobenzoic acid
Oxidobenzoic acid
Other names
Peroxybenzoic acid
Perbenzoic acid
Benzoperoxoic acid
Hydroxy benzoate
Benzoyl hydroperoxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.056
EC Number
  • 202-260-2
MeSH C017611
UNII
  • InChI=1S/C7H6O3/c8-7(10-9)6-4-2-1-3-5-6/h1-5,9H ☒N
    Key: XCRBXWCUXJNEFX-UHFFFAOYSA-N ☒N
  • InChI=1/C7H6O3/c8-7(10-9)6-4-2-1-3-5-6/h1-5,9H
    Key: XCRBXWCUXJNEFX-UHFFFAOYAA
  • OOC(=O)c1ccccc1
Properties
C7H6O3
Molar mass 138.12 g/mol
Melting point 41 to 42 °C (106 to 108 °F; 314 to 315 K)[2]
Acidity (pKa) 7.8[2]
Related compounds
Related compounds
 m-Chloroperoxybenzoic acid
Hydrogen peroxide
Benzoic 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

Like other peroxyacids, it may be used to generate epoxides, such as styrene oxide from styrene:[5]

Prilezhaev Reaction

References
  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 749, 761. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. Elvers, B. et al. (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A19, Wiley, p. 206
  3. Silbert, L. S.; Siegel, E.; Swern, D. (1964). "Peroxybenzoic Acid". Org. Synth. 44: 81. doi:10.15227/orgsyn.044.0081.
  4. Géza Braun (1928). "Perbenzoic Acid". Org. Synth. 8: 30. doi:10.15227/orgsyn.008.0030.
  5. Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Organic Syntheses.; Collective Volume, vol. 1, p. 494
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