Structure of Anthracene:
Anthracene is a polycyclic aromatic hydrocarbon with three fused benzene rings arranged in a linear structure.
The molecular formula is C14H10, and it is isomeric with phenanthrene.
Synthesis:
From Coal Tar:
Anthracene is also isolated from the high boiling fraction of coal tar.
Laboratory Synthesis (Elbs Reaction):
Cyclodehydration: Ortho-benzoyltoluene is cyclodehydrated to form anthracene.
Aromatization: The intermediate is aromatized to produce anthracene.
the intermediate is aromatized to produce anthracene.
O-Benzoyltoluene → Cyclodehydration → Anthracene
Reactions:
Electrophilic Substitution:
Nitration: Anthracene reacts with nitric acid to form 9-nitroanthracene.
C14H10 + HNO3 → H2SO4 (reagents) → C14H9NO2 + H2O
Sulfonation: Anthracene reacts with sulfuric acid to form anthracene sulfonic acid.
C14H10 + H2SO4 (reagents) → C14H9SO3H + H2O
Oxidation:
Anthracene can be oxidized to anthraquinone using chromic acid or other strong oxidizing agents.
C14H10 + 2[O] → C14H8(O)2
Derivatives:
Anthraquinone: An important industrial chemical used in the production of dyes and hydrogen peroxide.
Dyes: Anthracene derivatives are the basis of various dyes, especially anthraquinone dyes.
Medicinal Uses:
Anthraquinone Derivatives: Many anthraquinone derivatives are used in medicine as laxatives (e.g., senna, cascara), and some have been studied for their anti-cancer properties.