1,2,3,4-Tetraphenylnaphthalene

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1,2,3,4-Tetraphenylnaphthalene[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1,2,3,4-Tetra(phenyl)naphthalene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.151.838
Properties
C34H24
Molar mass 432.55 g/mol
Melting point 199 to 201 °C (390 to 394 °F; 472 to 474 K)
Hazards
R-phrases (outdated) R36/37/38
S-phrases (outdated) S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2] It has two crystalline forms, and therefore has two different melting points.

References[edit]

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