anthracene

Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) with the chemical formula C14H10. It consists of three linearly fused benzene rings, making a planar, highly conjugated molecule. It is the simplest linear acene and serves as a reference compound in PAH chemistry and applications.

Occurrence and production: Anthracene occurs in coal tar and, to a lesser extent, in certain crude petroleum fractions. It is produced commercially by distillation and processing of coal tar, with additional recovery from heavy fractions of petroleum and related byproducts. It can also be obtained from the purification of coal tar pitches.

Properties: It is a colorless to white crystalline solid with a melting point around 216°C. It is sparingly soluble in water but soluble in many organic solvents. Under ultraviolet light, anthracene exhibits blue fluorescence, a feature exploited in some fluorescence studies and optical applications.

Chemistry: The central 9,10-positions of anthracene are particularly reactive in Diels–Alder reactions, enabling the formation of diverse adducts. The compound readily undergoes oxidation to give anthraquinone (C14H8O2), a key intermediate in dye production. Hydrogenation yields 9,10-dihydroanthracene. These reactivities make anthracene a versatile precursor for dyes, organic pigments, and various functional materials.

Applications: The principal industrial use of anthracene is as a precursor to anthraquinone, which is widely used to manufacture anthraquinone-based dyes and related products. It also serves as a building block in the development of organic semiconductors, scintillators, and other materials in chemical and materials research.

Safety: Anthracene is a PAH and can pose environmental and health concerns if released or inhaled as dust. Handling should minimize inhalation and skin contact, and appropriate safety and environmental controls should be used when processing or storing the material.