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

| Density = 0.9782 g/cm3

| MeltingPtC = 52.0 to 52.5

| MeltingPt_ref =

| BoilingPtC = 284

| BoilingPt_ref =

| Solubility = Insoluble

| MagSus = −126.8·10−6 cm3/mol }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC =

| AutoignitionPt =

}}

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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.}}

See also

References

{{reflist}}

Category:Hydrocarbons

Category:Benzyl compounds

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