Phenanthren

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with the chemical formula C14H10. It comprises three fused benzene rings arranged in an angular, non-linear fashion, giving a planar, highly conjugated molecule. It is an isomer of anthracene, which shares the same formula but has a linear arrangement of rings.

Occurrence and synthesis: Phenanthrene occurs naturally in coal tar and crude oil and is formed during incomplete combustion of organic matter. It is also produced industrially as a standard reference material and as a precursor in some organic synthesis pathways.

Physical properties: A colorless to pale-yellow solid at room temperature, phenanthrene is hydrophobic and has very low water solubility. It dissolves in many organic solvents and has a relatively high boiling point. Its molecular weight is 178.23 g/mol. Its melting point is around 100–102 °C.

Reactivity and derivatives: As a polycyclic aromatic hydrocarbon, it undergoes typical electrophilic substitution reactions and can be oxidized to various phenanthrene derivatives, including quinones and hydroxylated forms, under appropriate conditions.

Applications and significance: In environmental and toxicological research, phenanthrene is used as a model compound for polycyclic aromatic hydrocarbons to study fate, transport, and biological effects of PAHs. It serves as a reference material in chromatographic analyses and as a building block for the synthesis of dyes and organic pigments.

Safety: Phenanthrene poses health and environmental risks as part of PAH mixtures. Handling requires appropriate protective equipment to avoid inhalation and dermal exposure, and it should be managed under standard laboratory safety practices.