Bibenzyl
Bibenzyl is the organic compound with the formula (C6H5CH2)2. It can be viewed as a derivative of ethane in which one phenyl group is bonded to each carbon atom. It is a colorless solid.
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| Names | |
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| Preferred IUPAC name
1,1'-(Ethane-1,2-diyl)dibenzene | |
| Other names
1,2-Diphenylethane Dibenzil Dibenzyl Dihydrostilbene sym-Diphenylethane | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.816 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C14H14 | |
| Molar mass | 182.266 g·mol−1 |
| Appearance | Crystalline solid[1] |
| Density | 0.9782 g/cm3[1] |
| Melting point | 52.0 to 52.5 °C (125.6 to 126.5 °F; 325.1 to 325.6 K)[1] |
| Boiling point | 284 °C (543 °F; 557 K)[1] |
| Insoluble | |
| -126.8·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Occurrences
The compound is the product from the coupling of a pair of benzyl radicals.[2]
Bibenzyl forms the central core of some natural products like dihydrostilbenoids[3] and isoquinoline alkaloids. Marchantins are a family of bis(bibenzyl)-containing macrocycles.[4]
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References
- The Merck Index, 11th Edition, 1219
- Girard, P.; Namy, J. L.; Kagan, H. B. (1980). "Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents". Journal of the American Chemical Society. 102: 2693–8. doi:10.1021/ja00528a029.CS1 maint: uses authors parameter (link)
- John Gorham; Motoo Tori; Yoshinori Asakawa (1995). The biochemistry of the stilbenoids. Springer. ISBN 0-412-55070-9.
- "The chemistry of macrocyclic bis(bibenzyls)". Natural Product Reports. 12: 69–75. 1995. doi:10.1039/NP9951200069.
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