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1,1'-Binaphthyl

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1,1'-Binaphthyl
Names
Preferred IUPAC name 1,1′-Binaphthalene
Other names 1-Naphthalen-1-ylnaphthalene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.155 Edit this at Wikidata
EC Number
  • 210-070-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H14/c1-3-11-17-15(7-1)9-5-13-19(17)20-14-6-10-16-8-2-4-12-18(16)20/h1-14HKey: ZDZHCHYQNPQSGG-UHFFFAOYSA-N
SMILES
  • C1=CC=C2C(=C1)C=CC=C2C3=CC=CC4=CC=CC=C43
Properties
Chemical formula C20H14
Molar mass 254.332 g·mol
Appearance Colorless solid
Density 1.299 g/cm
Melting point 160 °C (320 °F; 433 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,1'-Binaphthyl is an organic compound with the formula (C10H7)2. It is one of the dimers of naphthalene (or literally: dimers of naphthyl). A colorless solid, it has attracted some attention because the atropisomers can be isolated due to hindered rotation between the two naphthyl subunits. The halflife of the racemization is 14.5 min. at 50 °C. Substituted derivatives of this parent species, e.g. binaphthol, exhibit much higher barriers to racemization.

References

  1. Pu, Lin (1998). "1,1'-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials". Chemical Reviews. 98 (7): 2405–2494. doi:10.1021/cr970463w. PMID 11848968.
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