Ethylbenzene hydroperoxide

Ethylbenzene hydroperoxide
Names
IUPAC name
1-hydroperoxyethylbenzene
Other names
α-methylbenzyl hydroperoxide, 1-phenylethyl hydroperoxid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.402 Edit this at Wikidata
EC Number
  • 221-341-3
UNII
  • InChI=1S/C8H10O2/c1-7(10-9)8-5-3-2-4-6-8/h2-7,9H,1H3
    Key: GQNOPVSQPBUJKQ-UHFFFAOYSA-N
  • CC(C1=CC=CC=C1)OO
Properties
Appearance colorless liquid
Density 1.07500 g/cm3
Boiling point 45 °C (113 °F; 318 K) 0.05 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethylbenzene hydroperoxide is the organic compound with the formula C6H5CH(O2H)CH3. A colorless liquid, EBHP is a common hydroperoxide. It has been used as an O-atom donor in organic synthesis. It is chiral. Together with tert-butyl hydroperoxide and cumene hydroperoxide, ethylbenzene hydroperoxide is important commercially.[1]

The compound is produced by direct reaction of ethylbenzene with oxygen, an autoxidation.[2]

References

  1. ^ Roger A. Sheldon (1983). "Synthesis and uses of alkyl hydroperoxides and dialkyl peroxides". In Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 161–200. doi:10.1002/9780470771730.ch6. ISBN 978-0-471-10218-2.
  2. ^ Hermans, Ive; Peeters, Jozef; Jacobs, Pierre A. (2007). "Autoxidation of Ethylbenzene: The Mechanism Elucidated". The Journal of Organic Chemistry. 72 (8): 3057–3064. doi:10.1021/jo070040m. PMID 17362045.