9,10-Dihydroanthracene

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 as a hydrogen-donor.[2]

9,10-Dihydroanthracene
Names
Preferred IUPAC name
9,10-Dihydroanthracene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.398
UNII
  • InChI=1S/C14H12/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-8H,9-10H2
    Key: WPDAVTSOEQEGMS-UHFFFAOYSA-N
  • c1ccc2c(c1)Cc3ccccc3C2
Properties
C14H12
Molar mass 180.250 g·mol−1
Appearance white solid
Density 1.19 g mL−1[1]
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

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,[3] an application of the Bouveault–Blanc reduction. 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- carbon–hydrogen bonds are estimated at 78 kcal mol−1. Thus these bonds are about 20% weaker than typical C–H bonds.

References
  1. Reboul, J. P.; Oddon, Y.; Caranoni, C.; Soyfer, J. C.; Barbe, J.; Pèpe, G. (1987). "Structure du Dihydro-9,10 Anthracène. Support Tricyclique de Médicaments Psychotropes". Acta Crystallographica Section C Crystal Structure Communications. 43 (3): 537–539. doi:10.1107/S010827018709512X.
  2. Collin, Gerd; Höke, Hartmut; Talbiersky, Jörg (2006). "Anthracene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_343.pub2. ISBN 9783527303854.
  3. Bass, K. C. (1962). "9,10-Dihydroanthracene". Organic Syntheses. 42: 48. doi:10.15227/orgsyn.042.0048.
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