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]
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 (8): 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.
- Keserű, G. M.; Nógrádi, M. (1995). "The chemistry of macrocyclic bis(bibenzyls)". Natural Product Reports. 12: 69–75. doi:10.1039/NP9951200069.
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