Phenanthrene

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) consisting of three fused benzene rings. The name 'phenanthrene' is derived from the two terms 'phenyl' and 'anthracene'. It is a white crystalline substance, which is insoluble in water but soluble in organic solvents. Phenanthrene is used in the production of drugs, explosives, and pesticides.

Structure and Properties[edit | edit source]

Phenanthrene is a planar molecule, with the molecular formula C14H10. The carbon atoms in phenanthrene are arranged in a three-ring system, with the central ring sharing two sides with the other two rings. This structure is reflected in its IUPAC name: 1,2:3,4-dibenzonaphthalene.

Phenanthrene has a molar mass of 178.23 g/mol and a density of 1.179 g/cm3. It has a melting point of 100.2 °C and a boiling point of 340 °C. It is less reactive than its isomer anthracene.

Synthesis[edit | edit source]

Phenanthrene can be synthesized by various methods, including the Haworth reaction, the Barton-Zard synthesis, and the Friedel-Crafts reaction. It can also be obtained from coal tar, a by-product of the production of coke and coal gas from coal.

Uses[edit | edit source]

Phenanthrene is used in the synthesis of various drugs, including phenanthridine derivatives, which have anti-cancer properties. It is also used in the production of explosives and pesticides. In addition, it is used as a starting material in the synthesis of other polycyclic aromatic hydrocarbons.

Health Effects[edit | edit source]

Exposure to phenanthrene can cause skin and eye irritation. Ingestion can lead to nausea, vomiting, and abdominal pain. Long-term exposure can lead to respiratory problems and may have carcinogenic effects.

Environmental Impact[edit | edit source]

Phenanthrene is a common pollutant in the environment, mainly due to the incomplete combustion of fossil fuels. It is toxic to aquatic life and can bioaccumulate in the food chain.