Benzil
| Benzil | |
|---|---|
| Benzil | |
| General | |
| Systematic name | 1,2-diphenylethanedione |
| Other names | dibenzoyl bibenzoyl diphenylglyoxal |
| Molecular formula | C14H10O2 |
| SMILES | O=C(C(=O)c1ccccc1)c2ccccc2 |
| Molar mass | 210.23 g/mol |
| Appearance | yellow crystals or powder |
| CAS number | [134-81-6] |
| Properties | |
| Density and phase | 1.23 g/cm3, solid (1.255 g/cm3, x-ray) |
| Solubility in water | insoluble |
| Solubility in ethanol | soluble |
| Solubility in diethyl ether | soluble |
| Solubility in benzene | soluble |
| Melting point | 94.43-95.08 °C |
| Boiling point | 346-348 °C (619-621 K) |
| Structure | |
| Crystal structure | P31,221 Acta Cryst. B43 398 (1987) |
| Dipole moment | 3.8 D Spectrochim. Acta A60 (8-9) 1805 (2004) |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Irritant |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n: J. Phys. D Appl. Phys. 24 1187 (1991) εr: Bull. Mater. Sci. 19(5) 791 (1996) |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS spectral data |
| Related compounds | |
| Related diketones | biacetyl |
| Related compounds | benzophenone glyoxal benzil |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Benzil is the organic compound with the formula (C6H5CO)2, generally abbreviated (PhCO)2. This diketone is used as an intermediate in organic synthesis. Benzil is also employed as a photoinitiator for free-radical curing of polymer networks. Ultraviolet radiation decomposes benzil, creating free-radical species which propagate throughout polymer material, creating cross-links 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.[1]
- PhC(O)CH(OH)Ph + 2 Cu2+ → PhC(O)C(O)Ph + 2 H+ + 2 Cu+
A classical organic reaction of benzil is the Benzilic acid rearrangement to benzilic acid.
References
- ↑ Clarke, H. T.; Dreger.E. E. (1941). "Benzil". Org. Synth.; Coll. Vol. 1: 87.
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