Anthracene

Anthracene
Chemical name	Anthracene
Chemical formula	C14H10
Molecular mass	178.23 g/mol
Density	1.099 g/ml
Melting point	217.5 °C
Boiling point	340 °C
CAS number	120-12-7
SMILES	C1(C=C(C=CC=C2)C2=C3)=C3C=CC=C1

In chemistry, anthracene is a solid polycyclic aromatic hydrocarbon consisting of three benzene rings derived from coal-tar. Anthracene is used in the artificial production of the red dye alizarin. It is also used in wood preservatives, insecticides, and coating materials. Anthracene is colorless but exhibits a blue fluorescence under ultraviolet light.

Anthracene has the ability to photodimerize with irradiation by UV light. This results in considerable changes in the physical properties of the material.

The dimer is connected by two covalent bonds resulting from the [4+4] cycloaddition. The dimer reverts to anthracene thermally or with UV irradiation below 300 nm. The reversible bonding and photochromic properties of anthracenes is the basis of many potential applications using poly and monosubstituted anthracene derivatives. The reaction is sensitive to oxygen.

In most other reactions of anthracene, the central ring is also targeted. Electrophilic substitution occurs at the "9" and "10" positions of the center ring, and oxidation of anthracene occurs readily, giving anthraquinone, C₁₄H₈O₂ (below).