9,10-Dihydroanthracene

9,10-Dihydroanthracene
Identifiers
613-31-0
Properties
C14H12
Molar mass 180.25
Appearance white solid
Density 0.88 g/mL
Melting point 108 to 109 °C (226 to 228 °F; 381 to 382 K)
Boiling point 312 °C (594 °F; 585 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

9,10-Dihydroanthracene is an organic compound that is derived from the polycyclic aromatic hydrocarbon anthracene. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a carrier of H2 in various chemical reactions.[1]

Preparation

Because the aromaticity is not compromised for the flanking rings, anthracene is susceptible to hydrogenation at the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/ethanol under Bouveault–Blanc reduction.[2] The reduction can be effected by magnesium as well. Finally, it can also be prepared by the coupling of benzyl chloride using aluminium chloride as a catalyst.

The bond dissociation energy for the 9- and 10-C-H bonds are estimated at 78 kcal/mol. Thus these bonds are about 20% weaker than typical C-H bonds.

References

  1. Gerd Collin, Hartmut Höke and Jörg Talbiersky "Anthracene" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a02_343.pub2
  2. K. C. Bass "9,10-Dihydroanthracene" Organic Syntheses, 1962, Vol. 42, p.48ff. doi:10.15227/orgsyn.042.0048
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