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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34047 ;
ChEMBL	ChEMBL440895 ;
ChemSpider	7364 ;
ECHA InfoCard	100.002.816
PubChem CID	7647;
UNII	007C07V77Z ;
CompTox Dashboard (EPA)	DTXSID8041668 ;
	InChI InChI=1S/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2 Key: QWUWMCYKGHVNAV-UHFFFAOYSA-N ; 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;
	SMILES c1ccc(cc1)CCc2ccccc2;
Properties
Chemical formula	C14H14
Molar mass	182.266 g·mol−1
Appearance	Crystalline solid
Density	0.9782 g/cm3
Melting point	52.0 to 52.5 °C (125.6 to 126.5 °F; 325.1 to 325.6 K)
Boiling point	284 °C (543 °F; 557 K)
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). verify (what is ?) Infobox references

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]

References

^ ^a ^b ^c ^d The Merck Index, 11th Edition, 1219
^ "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. 1980. doi:10.1021/ja00528a029. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
^ 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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[Merck-1] The Merck Index, 11th Edition, 1219

[2] "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. 1980. doi:10.1021/ja00528a029. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[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.

[1]

[2]

[3]

[4]

Occurrences

See also

References