Ethylbenzene hydroperoxide

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]

Ethylbenzene hydroperoxide
Names
IUPAC name
1-hydroperoxyethylbenzene
Other names
α-methylbenzyl hydroperoxide, 1-phenylethyl hydroperoxid
Identifiers
3D model (JSmol)
ECHA InfoCard 100.019.402
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).
Infobox references

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

References
  1. Roger A. Sheldon (1983). Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771730.ch6.
  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.
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