C14H10, melting point 216°C. A colourless, cancer-causing, aromatic compound isolated from coal tar. Its blue fluorescence is used in scintillation counters to detect ?-particles. Oxidized to anthraquinone, it is the raw material for the alizarin series of dyestuffs.
Synthesis
A classis method for the preparation of anthracene in the laboratory is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction (Karl Elbs, 1858-1933).
Reactions
Anthracene has the ability to photodimerize with irradiation by UV light. The reversible bonding and photochromic properties of anthracenes is the basis of many potential applications using poly and monosubstituted anthracene derivatives.
In most other reactions of anthracene, the central ring is also targeted, as it is the most highly reactive. Electrophilic substitution occurs at the "9" and "10" positions of the center ring, and oxidation of anthracene occurs readily, giving anthraquinone, C14H8O2 (below).
Uses
Anthracene can also have a hydroxyl group to form 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and napthol, and hydroxyanthracene is also called anthrol, and anthracenol.
Anthracene is an organic semiconductor.
Anthracene is used as a scintillator for detectors of electrons and alpha particles.
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