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Revision as of 00:59, 6 April 2012 editRezabot (talk | contribs)Extended confirmed users48,194 editsm r2.7.1) (Robot: Adding fa:بی‌بنزیل← Previous edit Latest revision as of 22:48, 26 April 2023 edit undoTrappist the monk (talk | contribs)Administrators479,902 editsm →Occurrences: cite repair;Tag: AWB 
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{{Chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 486407303
| ImageFile = Bibenzyl.svg | ImageFile = Bibenzyl.svg
| ImageSize = 200px | ImageSize = 200px
| IUPACName = 1,1’-Ethane-1,2-diyldibenzene | PIN = 1,1′-(Ethane-1,2-diyl)dibenzene
| OtherNames = Dibenzil; Dibenzyl; Dihydrostilbene; 1,2-Diphenylethane; ''sym''-Diphenylethane | OtherNames = 1,2-Diphenylethane<br />Dibenzil<br />Dibenzyl<br />Dihydrostilbene<br />''sym''-Diphenylethane
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 103-29-7 | CASNo = 103-29-7
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem = 7647
| ChemSpiderID = 7364 | ChEMBL = 440895
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | SMILES = c1ccc(cc1)CCc2ccccc2
| ChEBI = 34047
⚫ | 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
| UNII_Ref = {{fdacite|changed|FDA}}
⚫ | StdInChI = 1S/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2
| UNII = 007C07V77Z
⚫ | StdInChIKey = QWUWMCYKGHVNAV-UHFFFAOYSA-N
⚫ | 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 |Section2={{Chembox Properties
| C=14|H=14 | C=14|H=14
| Appearance = Crystalline solid<ref name=Merck>'']'', 11th Edition, '''1219'''</ref> | Appearance = Crystalline solid<ref name=Merck>'']'', 11th Edition, '''1219'''</ref>
| Density = 0.9782 g/cm<sup>3</sup><ref name=Merck/> | Density = 0.9782 g/cm<sup>3</sup><ref name=Merck/>
| MeltingPtCL = 52.0 | MeltingPtC = 52.0 to 52.5
⚫ | MeltingPt_ref = <ref name=Merck/>
| MeltingPtCL = 52.5
⚫ | BoilingPtC = 284
⚫ | Melting_notes = <ref name=Merck/>
⚫ | BoilingPt_ref = <ref name=Merck/>
⚫ | BoilingPtC = 284
⚫ | Solubility = Insoluble
⚫ | Boiling_notes = <ref name=Merck/>
| MagSus = -126.8·10<sup>−6</sup> cm<sup>3</sup>/mol }}
⚫ | Solubility = Insoluble
⚫ |Section3={{Chembox Hazards
}}
| MainHazards =
⚫ | Section3 = {{Chembox Hazards
| MainHazards = | FlashPtC =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}


'''Bibenzyl''' ('''1,2-diphenylethane''') is an ] ] that can be considered a derivative of ] in which one ] is attached to each carbon atom. '''Bibenzyl''' is the ] with the formula (C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>)<sub>2</sub>. It can be viewed as a derivative of ] in which one ] is bonded to each carbon atom. It is a colorless solid.


==Occurrences ==
⚫ Bibenzyl forms the central core of some ] ]s<ref>{{cite book | title = The biochemistry of the stilbenoids | author = John Gorham, Motoo Tori, Yoshinori Asakawa | publisher = Springer | year = 1995 | isbn = 0-412-55070-9 }}</ref> and ] ]s.
The compound is the product from the coupling of a pair of ] radicals.<ref>{{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=], H. B. |journal=Journal of the American Chemical Society|year=1980|volume=102|issue=8|pages=2693–8|doi=10.1021/ja00528a029}}</ref>


⚫ Bibenzyl forms the central core of some ]s like ]s<ref>{{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 }}</ref> and ] ]s. Marchantins are a family of bis(bibenzyl)-containing macrocycles.<ref>{{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.}}</ref>
⚫ ==See also==

⚫ == See also ==
* ] * ]
* ] * ]


==References== == References ==
{{reflist}} {{reflist}}


] ]
] ]




{{hydrocarbon-stub}} {{hydrocarbon-stub}}

]
]

Latest revision as of 22:48, 26 April 2023

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.816 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2Key: QWUWMCYKGHVNAV-UHFFFAOYSA-N
  • InChI=1/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2Key: QWUWMCYKGHVNAV-UHFFFAOYAL
SMILES
  • c1ccc(cc1)CCc2ccccc2
Properties
Chemical formula C14H14
Molar mass 182.266 g·mol
Appearance Crystalline solid
Density 0.9782 g/cm
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 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) 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.

Bibenzyl forms the central core of some natural products like dihydrostilbenoids and isoquinoline alkaloids. Marchantins are a family of bis(bibenzyl)-containing macrocycles.

See also

References

  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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