Bibenzyl
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 486407303
| ImageFile = Bibenzyl.svg
| ImageSize = 200px
| PIN = 1,1′-(Ethane-1,2-diyl)dibenzene
| OtherNames = 1,2-Diphenylethane
Dibenzil
Dibenzyl
Dihydrostilbene
sym-Diphenylethane
|Section1={{Chembox Identifiers
| CASNo = 103-29-7
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 440895
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34047
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 007C07V77Z
| PubChem = 7647
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7364
| SMILES = c1ccc(cc1)CCc2ccccc2
| InChI = 1/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2
| InChIKey = QWUWMCYKGHVNAV-UHFFFAOYAL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QWUWMCYKGHVNAV-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=14|H=14
| Appearance = Crystalline solidThe Merck Index, 11th Edition, 1219
| MeltingPtC = 52.0 to 52.5
| BoilingPtC = 284
| Solubility = Insoluble
| MagSus = −126.8·10−6 cm3/mol }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC =
| AutoignitionPt =
}}
}}
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.{{cite journal|title=Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents|author1=Girard, P. |author2=Namy, J. L. |author3=Kagan, H. B. |journal=Journal of the American Chemical Society|year=1980|volume=102|issue=8|pages=2693–8|doi=10.1021/ja00528a029}}
Bibenzyl forms the central core of some natural products like dihydrostilbenoids{{cite book | title = The biochemistry of the stilbenoids |author1=John Gorham |author2=Motoo Tori |author3=Yoshinori Asakawa | publisher = Springer | year = 1995 | isbn = 0-412-55070-9 }} and isoquinoline alkaloids. Marchantins are a family of bis(bibenzyl)-containing macrocycles.{{cite journal|title=The chemistry of macrocyclic bis(bibenzyls)|journal=Natural Product Reports|year=1995|volume=12|pages=69–75|doi=10.1039/NP9951200069|last1=Keserű|first1=G. M.|last2=Nógrádi|first2=M.}}