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1,2,3,4-Tetraphenylnaphthalene

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1,2,3,4-Tetraphenylnaphthalene
Skeletal formula
Ball-and-stick model
Names
IUPAC name 1,2,3,4-Tetra(phenyl)naphthalene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.151.838 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C34H24/c1-5-15-25(16-6-1)31-29-23-13-14-24-30(29)32(26-17-7-2-8-18-26)34(28-21-11-4-12-22-28)33(31)27-19-9-3-10-20-27/h1-24HKey: UCTTYTFENYGAPP-UHFFFAOYSA-N
  • InChI=1/C34H24/c1-5-15-25(16-6-1)31-29-23-13-14-24-30(29)32(26-17-7-2-8-18-26)34(28-21-11-4-12-22-28)33(31)27-19-9-3-10-20-27/h1-24HKey: UCTTYTFENYGAPP-UHFFFAOYAS
SMILES
  • C1=CC=C(C=C1)C2=C(C(=C(C3=CC=CC=C32)C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6
  • c15ccccc1c(c2ccccc2)c(c3ccccc3)c(c4ccccc4)c5c6ccccc6
Properties
Chemical formula C34H24
Molar mass 432.55 g/mol
Melting point 199-201 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1,2,3,4-Tetraphenylnaphthalene is a polycyclic aromatic hydrocarbon commonly prepared in the undergraduate teaching laboratory as an introduction to the Diels-Alder reaction, in this case between benzyne (generated in situ) and tetraphenylcyclopentadienone. It has two crystalline forms, and therefore has two different melting points.

References

  1. 1,2,3,4-Tetraphenylnaphthalene at Sigma-Aldrich
  2. Organic Syntheses, Coll. Vol. 5, p.1037 (1973); Vol. 46, p.107 (1966). Link


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