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{{distinguish|benzyl}} |
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{{distinguish|benzyl}} |
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{{chembox |
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{{Chembox |
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|Watchedfields = changed |
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| verifiedrevid = 410983115 |
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|verifiedrevid = 443415454 |
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| Name = Benzil |
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|Name = Benzil |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Benzil-2D-skeletal.png |
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| ImageName = Benzil |
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|ImageFile = Benzil.svg |
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| ImageFile1 = Benzil-from-LT-monoclinic-xtal-CM-3D-balls.png |
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|ImageName = Benzil |
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|ImageFile1 = Benzil-from-LT-monoclinic-xtal-CM-3D-balls.png |
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| ImageFile2 = Benzil-from-LT-monoclinic-xtal-CM-3D-SF.png |
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|ImageFile2 = Benzil-from-LT-monoclinic-xtal-CM-3D-SF.png |
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|PIN = Diphenylethanedione <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| IUPACName = 1,2-diphenylethane-1,2-dione |
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|SystematicName = 1,2-Diphenylethane-1,2-dione |
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| OtherNames = dibenzoyl<br />bibenzoyl<br />diphenylglyoxal |
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|OtherNames = Diphenylethane-1,2-dione<br />Benzil<br />Dibenzoyl<br />Bibenzoyl<br />Diphenylglyoxal |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChEBI = 51507 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = O=C(C(=O)c1ccccc1)c2ccccc2 |
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|ChEBI = 51507 |
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| InChI = 1/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H |
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|SMILES = O=C(C(=O)c1ccccc1)c2ccccc2 |
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| InChIKey = WURBFLDFSFBTLW-UHFFFAOYAZ |
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|InChI = 1/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H |
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| SMILES1 = c1ccc(cc1)C(=O)C(=O)c2ccccc2 |
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|InChIKey = WURBFLDFSFBTLW-UHFFFAOYAZ |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|SMILES1 = c1ccccc1C(=O)C(=O)c2ccccc2 |
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| ChEMBL = 189886 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 189886 |
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| StdInChI = 1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H |
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| StdInChIKey = WURBFLDFSFBTLW-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = WURBFLDFSFBTLW-UHFFFAOYSA-N |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=8329 |
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|ChemSpiderID = 8329 |
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| CASNo = 134-81-6 |
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|CASNo = 134-81-6 |
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| PubChem = 8651 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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}} |
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|UNII = S85X61172J |
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| Section2 = {{Chembox Properties |
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|PubChem = 8651 |
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|C=14|H=10|O=2 |
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|EC_number = 205-157-0 |
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| Appearance = yellow crystals or powder |
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|RTECS = DD1925000 |
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| Density = 1.23 g/cm<sup>3</sup>, solid (1.255 g/cm<sup>3</sup>, x-ray) |
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|Beilstein = 608047 |
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| Solubility = insoluble |
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}} |
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| Solvent = ] |
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|Section2={{Chembox Properties |
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| SolubleOther = soluble |
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|C=14 | H=10 | O=2 |
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| Solvent = ] |
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|Appearance = yellow crystalline powder |
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| SolubleOther = soluble |
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|Density = 1.23 g/cm<sup>3</sup>, solid (1.255 g/cm<sup>3</sup>, x-ray) |
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| Solvent = ] |
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|Solubility = insoluble |
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| SolubleOther = soluble |
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|Solvent1 = ethanol |
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| MeltingPt = 94.43-95.08 °C, 201.97-203.14 °F, 367-368 K |
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|Solubility1 = soluble |
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| BoilingPt = 346- 348 °C, 654.8-658.4 °F, 619-621 K |
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|Solvent2 = diethyl ether |
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}} |
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|Solubility2 = soluble |
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| Section3 = {{Chembox Structure |
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|Solvent3 = benzene |
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| CrystalStruct = P3<sub>1,2</sub>21<ref>''Acta Cryst.'' B43 398 (1987)</ref> |
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|Solubility3 = soluble |
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| Dipole = 3.8 ]<ref>''Spectrochim. Acta'' A60 (8-9) 1805 (2004)</ref> |
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|MeltingPtF = 201.2 to 204.8 |
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}} |
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|BoilingPtF = 654.8 to 658.4 |
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| Section7 = {{Chembox Hazards |
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|MagSus = -118.6·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| ExternalMSDS = |
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}} |
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| MainHazards = ] |
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|Section3={{Chembox Structure |
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| FlashPt = |
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|CrystalStruct = P3<sub>1,2</sub>21<ref>''Acta Crystallogr.'' B43 398 (1987)</ref> |
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| RPhrases = |
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|Dipole = 3.8 ]<ref>''Spectrochim. Acta'' A60 (8-9) 1805 (2004)</ref> |
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| SPhrases = |
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}} |
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| NFPA-H = 2 |
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|Section7={{Chembox Hazards |
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| NFPA-F = 1 |
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|MainHazards = ] |
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| NFPA-R = 0 |
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| NFPA-O = |
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|NFPA-H = 2 |
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|NFPA-F = 1 |
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}} |
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|NFPA-R = 0 |
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| Section8 = {{Chembox Related |
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|GHSPictograms = {{GHS07}} |
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| Function = ]s |
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|GHSSignalWord = Warning |
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| OtherFunctn = ] |
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|HPhrases = {{H-phrases|315|319|335}} |
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| OtherCpds = ]<br />]<br />benzil |
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|PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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}} |
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|LD50 = >3 g/kg (mouse, oral)<ref>{{cite web |title=Benzil |url=https://pubchem.ncbi.nlm.nih.gov/compound/Benzil#section=Toxicity |language=en}}</ref> |
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}} |
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|Section8={{Chembox Related |
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|OtherFunction_label = ]s |
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|OtherFunction = ] |
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|OtherCompounds = ]<br />]<br />] |
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}} |
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}} |
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'''Benzil''' (systematically known as 1,2-diphenylethane-1,2-dione) is the ] with the formula (]])<sub>2</sub>, generally abbreviated (]CO)<sub>2</sub>. This yellow solid is one of the most common ]s. Its main use is as a ] in ].<ref name=Ullmann>Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Wienheim. {{DOI|10.1002/14356007.a15_077}}</ref> |
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'''Benzil''' (i.e. '''Bz<sub>2</sub>''', systematically known as 1,2-diphenylethane-1,2-dione) is the ] with the formula (]])<sub>2</sub>, generally abbreviated (]CO)<sub>2</sub>. This yellow solid is one of the most common ]s. Its main use is as a ] in ].<ref name=Ullmann>Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a15_077}}</ref> |
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==Structure== |
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The compound's most noteworthy structural feature is the long ] of 1.54 ], which indicates the absence of pi-bonding between the two carbonyl centers. The PhCO centers are planar, but the pair of benzoyl groups are twisted with respect to the other with a ] of 117°.<ref>Quang. Shen, Kolbjoern. Hagen "Gas-phase molecular structure and conformation of benzil as determined by electron diffraction" J. Phys. Chem., 1987, 91 (6), pp 1357–1360. {{DOI|10.1021/j100290a017}}.</ref> In less ] analogues (], ], ] derivatives), the (RCO)<sub>2</sub> groups adopts a planar, anti-conformation. |
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==Applications== |
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== Structure == |
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The compound's most noteworthy structural feature is the long ] of 1.54 ], which indicates the absence of pi-bonding between the two carbonyl centers. The PhCO centers are planar, but the pair of benzoyl groups are twisted with respect to the other with a ] of 117°.<ref>Quang. Shen, Kolbjoern. Hagen "Gas-phase molecular structure and conformation of benzil as determined by electron diffraction" J. Phys. Chem., 1987, 91 (6), pp 1357–1360. {{doi|10.1021/j100290a017}}.</ref> In less ] analogues (], ], ] derivatives), the (RCO)<sub>2</sub> group adopts a planar, anti-conformation. |
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Most benzil is consumed for use in the free-radical ] of ] networks. ] radiation decomposes benzil, generating free-radical species within the material, promoting the formation of ]s. |
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===Reactions=== |
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== Applications == |
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Most benzil can be used as a photoinitiator in the free-radical ] of ] networks. It absorbs ] radiation at a wavelength of 260 nm, leading to decomposition with formation of free-radical species and formation of ]s within the material. However, it is a relatively poor photoinitiator, and is seldom used. It undergoes ], which allows the curing light to reach deeper layers of the material on longer exposure.<ref name="Green2010">{{Cite book | url=https://books.google.com/books?id=b1jRBQAAQBAJ&dq=benzil+photoinitiator&pg=PA31 |page= 31 |title = Industrial Photoinitiators: A Technical Guide|isbn = 9781439827468|last1 = Green|first1 = W. Arthur |date = 2010-04-22 |publisher= CRC Press |access-date=2022-05-21}}</ref> ] derivatives, such as ], have better properties for this application.<ref name="Green2010"/> |
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Benzil is a standard building block in ]. It condenses with amines to give ]s ligands. A classic ] of benzil is the ], in which base catalyses the conversion of benzil to benzilic acid. This reactivity is exploited in the preparation of the drug ]. Benzil also reacts with ] in an ] to give ]. |
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Benzil is a potent ] of human ]s, ]s involved in the hydrolysis of carboxylesters and many clinically used drugs.<ref>Wadkins. R. M. et al "Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J. Med. Chem., 2005 48 pp 2906–15.</ref> |
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==Preparation== |
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Benzil is prepared from ], which in turn is easily obtained via the ] from ].<ref>{{OrgSynth | author = Clarke, H. T.; Dreger.E. E. | title = Benzil | collvol = 1 | collvolpages = 87 | year = 1941 | prep = cv1p0087}}</ref> |
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:PhC(O)CH(OH)Ph + 2 Cu<sup>2+</sup> → PhC(O)C(O)Ph + 2 H<sup>+</sup> + 2 Cu<sup>+</sup> |
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==References== |
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=== Reactions === |
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Benzil is a standard building block in ]. It condenses with amines to give ] ligands. A classic ] of benzil is the ], in which base catalyses the conversion of benzil to ]. This reactivity is exploited in the preparation of the drug ]. Benzil also reacts with ] in an ] to give ]. |
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<references/> |
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== Preparation == |
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] |
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Benzil is prepared from ], for example with ]:<ref>{{cite journal|doi=10.1021/ed065p553|title=Synthesis of benzil from benzoin with copper(II) acetate|journal=Journal of Chemical Education|volume=65|issue=6|pages=553|year=1988|last1=Depreux|first1=P.|last2=Bethegnies|first2=G.|last3=Marcincal-Lefebvre|first3=A.|bibcode=1988JChEd..65..553D}}</ref> |
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:PhC(O)CH(OH)Ph + 2 Cu<sup>2+</sup> → PhC(O)C(O)Ph + 2 H<sup>+</sup> + 2 Cu<sup>+</sup> |
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Other suitable oxidizing agents such as ] (HNO<sub>3</sub>) are used routinely. |
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] (FeCl<sub>3</sub>) can be used as an inexpensive catalyst for this chemical conversion.<ref>{{cite journal|doi=10.4067/S0717-97072011000200008|title=One-Pot Synthesis Benzils from Aldehydes Via Nhc-Catalyzed Benzoin Dimerization Under Metal-Free Conditions in Water|journal=Journal of the Chilean Chemical Society|volume=56|issue=2|pages=663|year=2011|last1=Bi|first1=Xiaoxin|last2=Wu|first2=Lintao|last3=Yan|first3=Chaoguo|last4=Jing|first4=Xiaobi|last5=Zhu|first5=Hongxiang|doi-access=free}}</ref> |
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== References == |
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<references /> |
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