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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.816
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula
 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]
Solubility in water
 Insoluble
Magnetic susceptibility (χ)
 -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: 2693–8. doi:10.1021/ja00528a029.CS1 maint: uses authors parameter (link)
  3. John Gorham; Motoo Tori; Yoshinori Asakawa (1995). The biochemistry of the stilbenoids. Springer. ISBN 0-412-55070-9.
  4. "The chemistry of macrocyclic bis(bibenzyls)". Natural Product Reports. 12: 69–75. 1995. doi:10.1039/NP9951200069.


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