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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
Preferred IUPAC name 1,2,3,4-Tetraphenylnaphthalene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.151.838 Edit this at Wikidata
EC Number
  • 623-131-0
PubChem CID
UNII
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 to 201 °C (390 to 394 °F; 472 to 474 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
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

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, which acts as the dienophile, (generated in situ) and tetraphenylcyclopentadienone, which acts as the diene. It has two crystalline forms, and therefore has two different melting points.

References

  1. 1,2,3,4-Tetraphenylnaphthalene at Sigma-Aldrich
  2. "1,2,3,4-Tetraphenylnaphthalene". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  3. Organic Syntheses, Coll. Vol. 5, p.1037 (1973); Vol. 46, p.107 (1966). Link


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