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.

Bibenzyl
Names
Preferred IUPAC name
1,1′-(Ethane-1,2-diyl)dibenzene
Other names
1,2-Diphenylethane
Dibenzil
Dibenzyl
Dihydrostilbene
sym-Diphenylethane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.816
UNII
  • InChI=1S/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2 checkY
    Key: QWUWMCYKGHVNAV-UHFFFAOYSA-N checkY
  • InChI=1/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2
    Key: QWUWMCYKGHVNAV-UHFFFAOYAL
  • c1ccc(cc1)CCc2ccccc2
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]

See also

References
  1. The Merck Index, 11th Edition, 1219
  2. 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.
  3. John Gorham; Motoo Tori; Yoshinori Asakawa (1995). The biochemistry of the stilbenoids. Springer. ISBN 0-412-55070-9.
  4. 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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