Benzil
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| Benzil | |
|---|---|
 |
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| 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 |
| Solubility in water | insoluble |
| Solubility in ethanol | soluble |
| Solubility in diethyl ether | soluble |
| Solubility in benzene | soluble |
| Melting point | 94-95 °C (367-368 K) |
| Boiling point | 346-348 °C (619-621 K) |
| Structure | |
| Crystal structure | P31,221 Acta Cryst. B43 398 (1987) |
| Dipole moment | ? D |
| 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, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| 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 |
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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.
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.
[edit] References
- ^ Clarke, H. T.; Dreger.E. E. "Benzil" Organic Syntheses, Collected Volume 1, p.87 (1941).
[edit] External links
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