Chemistry:9,10-Dihydroanthracene

9,10-Dihydroanthracene

Names
Preferred IUPAC name 9,10-Dihydroanthracene
Identifiers
CAS Number	613-31-0
3D model (JSmol)	Interactive image
ChemSpider	11446
PubChem CID	11940
InChI 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
SMILES c1ccc2c(c1)Cc3ccccc3C2
Properties
Chemical formula	C14H12
Molar mass	180.250 g·mol−1
Appearance	white solid
Density	0.88 g mL−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

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.

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, an application of the Bouveault–Blanc reduction developed by Louis Bouveault and Gustave Louis Blanc in 1903. 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.