Peroxybenzoic acid

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 Edit this at Wikidata
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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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]

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

Prilezhaev Reaction
  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. ^ a b 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; Collected Volumes, vol. 1, p. 494.