1,2,3,4-Tetraphenylnaphthalene

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

1,2,3,4-Tetraphenylnaphthalene[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
1,2,3,4-Tetraphenylnaphthalene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.151.838
EC Number
  • 623-131-0
UNII
  • 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/h1-24H checkY
    Key: UCTTYTFENYGAPP-UHFFFAOYSA-N checkY
  • 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/h1-24H
    Key: UCTTYTFENYGAPP-UHFFFAOYAS
  • 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
C34H24
Molar mass 432.55 g/mol
Melting point 199 to 201 °C (390 to 394 °F; 472 to 474 K)
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315, H319, H335
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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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