Benzil
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219073303
2008-06-13T13:10:43Z
Puppy8800
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iw
{{Chembox new
| Name = Benzil
| ImageFile = Benzil-2D-skeletal-D.png
<!-- | ImageSize = 200px -->
| ImageName = Benzil
| ImageFile1 = Benzil-3D-balls.png
| ImageFile2 = Benzil-3D-vdW.png
| IUPACName = 1,2-diphenylethanedione
| OtherNames = dibenzoyl<br />bibenzoyl<br />diphenylglyoxal
| Section1 = {{Chembox Identifiers
| SMILES = O=C(C(=O)c1ccccc1)c2ccccc2
| CASNo = 134-81-6
| RTECS =
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>14</sub>H<sub>10</sub>O<sub>2</sub>
| MolarMass = 210.23 g/mol
| Appearance = yellow crystals or powder
| Density = 1.23 g/cm<sup>3</sup>, solid (1.255 g/cm<sup>3</sup>, x-ray)
| Solubility = insoluble
| Solvent = [[ethanol]]
| SolubleOther = soluble
| Solvent = [[diethyl ether]]
| SolubleOther = soluble
| Solvent = [[benzene]]
| SolubleOther = soluble
| MeltingPt = 94.43-95.08 °C
| BoilingPt = 619-621 K
}}
| Section3 = {{Chembox Structure
| CrystalStruct = P3<sub>1,2</sub>21<ref>''Acta Cryst.'' B43 398 (1987)</ref>
| Dipole = 3.8 [[Debye|D]]<ref>''Spectrochim. Acta'' A60 (8-9) 1805 (2004)</ref>
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| MainHazards = [[Irritant]]
| FlashPt =
| RPhrases =
| SPhrases =
}}<!--
| [[Refractive index|''n'']]:<I>J. Phys. D Appl. Phys.</I> 24 1187 (1991)<BR>[[Dielectric constant|ε<sub>r</sub>]]:<I>Bull. Mater. Sci.</I> 19(5) 791 (1996)
|-
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[NMR spectroscopy|NMR]], [[Mass spectrometry|MS]]<BR>
[http://www.woc.science.ru.nl/cgi-bin/view?benzil spectral data]<BR>
<I>Spectrochim. Acta</I> A58(14) 3127 (2002), IR
|-
-->
| Section8 = {{Chembox Related
| Function = [[diketone]]s
| OtherFunctn = [[biacetyl]]
| OtherCpds = [[benzophenone]]<br />[[glyoxal]]<br />benzil
}}
}}
'''Benzil''' is the [[organic compound]] with the formula ([[carbon|C]]<sub>6</sub>[[hydrogen|H]]<sub>5</sub>C[[oxygen|O]])<sub>2</sub>, generally abbreviated ([[phenyl|Ph]]CO)<sub>2</sub>. This [[diketone]] is used as an intermediate in [[organic synthesis]]. Benzil is also employed as a [[photoinitiator]] for free-radical [[Curing (chemistry)|curing]] of [[polymer]] networks. [[Uv|Ultraviolet radiation]] decomposes benzil, creating free-radical species which propagate throughout polymer material, creating [[cross-link]]s between individual polymer chains. Recently benzil has been identified as a selective inhibitor of carboxylesterase enzymes, proteins involved in the metabolism of esterified drugs and xenobiotics.
Benzil can be prepared in the laboratory by the [[benzoin condensation]] of [[benzaldehyde]] followed by oxidation of [[benzoin]] using [[copper sulfate]].<ref>{{OrgSynth | author = Clarke, H. T.; Dreger.E. E. | title = Benzil | collvol = 1 | collvolpages = 87 | year = 1941 | prep = cv1p0087}}</ref>
:PhC(O)CH(OH)Ph + 2 Cu<sup>2+</sup> → PhC(O)C(O)Ph + 2 H<sup>+</sup> + 2 Cu<sup>+</sup>
A classical [[organic reaction]] of benzil is the [[Benzilic acid rearrangement]] to benzilic acid.
==References==
<references/>
[[Category:Ketones]]
[[Category:Aromatic compounds]]
{{aromatic-stub}}
[[de:Benzil]]
[[fr:Benzile]]
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[[ja:ベンジル]]
[[zh:二苯基乙二酮]]