Hexaphenylbenzene

{{#if:534.6876C₄₂H₃₀454-456 °C|! style="background: #F8EABA; text-align: center;" colspan="2" | Properties

Hexaphenylbenzene
File:Hexaphenylbenzene.png
File:Hexaphenylbenzene xtal.png
IUPAC name 1,2,3,4,5,6-hexa(phenyl)benzene
Identifiers
CAS number	992-04-1 7pxY
PubChem	70432
ChemSpider	63611 7pxY
Jmol-3D images	Image 1
SMILES c1cc(ccc1)c3c(c(c(c(c3c2ccccc2)c4ccccc4)c5ccccc5)c6ccccc6)c7ccccc7 <p><p style="word-wrap: break-word;">
InChI InChI=1S/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30H 7pxY Key: QBHWPVJPWQGYDS-UHFFFAOYSA-N 7pxY InChI=1/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30H Key: QBHWPVJPWQGYDS-UHFFFAOYAG
Molecular formula	C42H30
Molar mass	534.6876
Melting point	454-456 °C
14pxY (verify) (what is: 10pxY/10pxN?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Hexaphenylbenzene is an aromatic compound composed of a benzene ring substituted with six phenyl rings.

It may be prepared through a Diels-Alder reaction by refluxing tetraphenylcyclopentadienone and diphenylacetylene in benzophenone or other high-temperature solvent.

Hexaphenylbenzene synthesis

Structure

File:Hexaphenylbenzene xtal perspective.png

Perspective view of the crystal structure of hexaphenylbenzene, showing the rotation of the phenyl rings. Hydrogen atoms have been omitted for clarity.

Due to steric congestion among the phenyl rings, the stable conformation of this molecule has the phenyl rings rotated out of the plane of the central benzene ring. In the crystalline form shown on the left, the molecule forms a propeller-like conformation in which the phenyl rings are rotated about 65°, while in the gas phase, they are perpendicular with some slight oscillations.

References

fa:هگزافنیل‌بنزن