9,10-Dihydroanthracene is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
that is derived from the
polycyclic aromatic hydrocarbon anthracene
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is ...
. 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 H
2 as a
hydrogen-donor.
Preparation
Because the
aromaticity is not compromised for the flanking rings, anthracene is susceptible to
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate org ...
at the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a h ...
, 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.
References
{{DEFAULTSORT:Dihydroanthracene, 9,10-
Anthracenes