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Benzil

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Not to be confused with benzyl.
Benzil
Benzil
Names
Preferred IUPAC name Diphenylethanedione
Systematic IUPAC name 1,2-Diphenylethane-1,2-dione
Other names Diphenylethane-1,2-dione
Benzil
Dibenzoyl
Bibenzoyl
Diphenylglyoxal
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 608047
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.689 Edit this at Wikidata
EC Number
  • 205-157-0
PubChem CID
RTECS number
  • DD1925000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10HKey: WURBFLDFSFBTLW-UHFFFAOYSA-N
  • InChI=1/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10HKey: WURBFLDFSFBTLW-UHFFFAOYAZ
SMILES
  • O=C(C(=O)c1ccccc1)c2ccccc2
  • c1ccccc1C(=O)C(=O)c2ccccc2
Properties
Chemical formula C14H10O2
Molar mass 210.232 g·mol
Appearance yellow crystalline powder
Density 1.23 g/cm, solid (1.255 g/cm, x-ray)
Melting point 94.0 to 96.0 °C; 201.2 to 204.8 °F; 367.1 to 369.2 K
Boiling point 346.0 to 348.0 °C; 654.8 to 658.4 °F; 619.1 to 621.1 K
Solubility in water insoluble
Solubility in ethanol soluble
Solubility in diethyl ether soluble
Solubility in benzene soluble
Magnetic susceptibility (χ) -118.6·10 cm/mol
Structure
Crystal structure P31,221
Dipole moment 3.8 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Irritant
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Lethal dose or concentration (LD, LC):
LD50 (median dose) >3 g/kg (mouse, oral)
Related compounds
Related diketones diacetyl
Related compounds benzophenone
glyoxal
bibenzil
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Benzil (i.e. Bz2, systematically known as 1,2-diphenylethane-1,2-dione) is the organic compound with the formula (C6H5CO)2, generally abbreviated (PhCO)2. This yellow solid is one of the most common diketones. Its main use is as a photoinitiator in polymer chemistry.

Structure

The compound's most noteworthy structural feature is the long carbon-carbon bond of 1.54 Å, 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 dihedral angle of 117°. In less hindered analogues (glyoxal, biacetyl, oxalic acid derivatives), the (RCO)2 group adopts a planar, anti-conformation.

Applications

Most benzil can be used as a photoinitiator in the free-radical curing of polymer networks. It absorbs ultraviolet radiation at a wavelength of 260 nm, leading to decomposition with formation of free-radical species and formation of cross-links within the material. However, it is a relatively poor photoinitiator, and is seldom used. It undergoes photobleaching, which allows the curing light to reach deeper layers of the material on longer exposure. Acetal derivatives, such as 2,2-dimethoxy-2-phenylacetophenone, have better properties for this application.

Benzil is a potent inhibitor of human carboxylesterases, enzymes involved in the hydrolysis of carboxylesters and many clinically used drugs.

Reactions

Benzil is a standard building block in organic synthesis. It condenses with amines to give diketimine ligands. A classic organic reaction of benzil is the benzilic acid rearrangement, in which base catalyses the conversion of benzil to benzilic acid. This reactivity is exploited in the preparation of the drug phenytoin. Benzil also reacts with 1,3-diphenylacetone in an aldol condensation to give tetraphenylcyclopentadienone.

Preparation

Benzil is prepared from benzoin, for example with copper(II) acetate:

PhC(O)CH(OH)Ph + 2 Cu → PhC(O)C(O)Ph + 2 H + 2 Cu

Other suitable oxidizing agents such as nitric acid (HNO3) are used routinely.

Iron(III) chloride (FeCl3) can be used as an inexpensive catalyst for this chemical conversion.

References

  1. Acta Crystallogr. B43 398 (1987)
  2. Spectrochim. Acta A60 (8-9) 1805 (2004)
  3. "Benzil".
  4. 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
  5. 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.
  6. ^ Green, W. Arthur (2010-04-22). Industrial Photoinitiators: A Technical Guide. CRC Press. p. 31. ISBN 9781439827468. Retrieved 2022-05-21.
  7. 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.
  8. Depreux, P.; Bethegnies, G.; Marcincal-Lefebvre, A. (1988). "Synthesis of benzil from benzoin with copper(II) acetate". Journal of Chemical Education. 65 (6): 553. Bibcode:1988JChEd..65..553D. doi:10.1021/ed065p553.
  9. Bi, Xiaoxin; Wu, Lintao; Yan, Chaoguo; Jing, Xiaobi; Zhu, Hongxiang (2011). "One-Pot Synthesis Benzils from Aldehydes Via Nhc-Catalyzed Benzoin Dimerization Under Metal-Free Conditions in Water". Journal of the Chilean Chemical Society. 56 (2): 663. doi:10.4067/S0717-97072011000200008.
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