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.

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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]

[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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[Merck-1] [1]
The Merck Index, 11th Edition, 1219

[2] [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] [3]
John Gorham; Motoo Tori; Yoshinori Asakawa (1995). The biochemistry of the stilbenoids. Springer. ISBN 0-412-55070-9.

[4] [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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[2]

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Bibenzyl

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Occurrences

See also

References

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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34047^Y
ChEMBL	ChEMBL440895^Y
ChemSpider	7364^Y
ECHA InfoCard	100.002.816
PubChem CID	7647
UNII	007C07V77Z^N
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^Y Key: QWUWMCYKGHVNAV-UHFFFAOYSA-N^Y 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^[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). N verify (what is ^YN ?) Infobox references