Bibenzyl

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
  • 103-29-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34047 checkY
ChEMBL
  • ChEMBL440895 checkY
ChemSpider
  • 7364 checkY
ECHA InfoCard 100.002.816 Edit this at Wikidata
PubChem CID
  • 7647
UNII
  • 007C07V77Z ☒N
CompTox Dashboard (EPA)
  • DTXSID8041668 Edit this at Wikidata
InChI
  • 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
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
Chemical compound

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.

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. ^ a b c d 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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