Benzil 2920473 219073303 2008-06-13T13:10:43Z Puppy8800 5404759 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> &rarr; 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]] [[lv:Benzils]] [[ja:ベンジル]] [[zh:二苯基乙二酮]]