Naphthalene

Naphthalene is a crystalline aromatic hydrocarbon, C₁₀H₈, whose two fused benzene rings form the simplest fused-ring aromatic system. It is obtained mainly from coal tar and petroleum and serves as a chemical feedstock.

Aromaticity: A stabilization associated with cyclic, conjugated molecules containing delocalized π electrons. Naphthalene’s ten π electrons are delocalized across both fused rings.
Phthalic anhydride: An organic anhydride used to manufacture plasticizers, resins, and dyes. Air oxidation of naphthalene is an industrial route to this chemical intermediate.
Coal tar: A complex dark liquid produced during the destructive distillation of coal. Coal tar was the historical source from which naphthalene was first isolated.
Naphthalene poisoning: Illness caused by exposure to or ingestion of naphthalene, which can damage red blood cells. Metabolism of naphthalene can trigger oxidative injury, especially in susceptible people.
Benzene: A six-carbon aromatic hydrocarbon consisting of a single six-membered ring. Benzene has one aromatic ring, whereas naphthalene fuses two rings.
Electrophilic aromatic substitution: A reaction in which an electrophile replaces hydrogen on an aromatic ring while aromaticity is restored. Naphthalene commonly reacts by substitution rather than addition, preserving its aromatic system.
Naphthalene sulfonic acid: A group of aromatic sulfonic acids derived by adding sulfonic acid groups to naphthalene. Sulfonated derivatives serve as intermediates for dyes and dispersing agents.
Michael Faraday: An English chemist and physicist whose discoveries included electromagnetic induction and benzene. Faraday isolated naphthalene from coal-tar oil in 1820.
Hemolytic anemia: Anemia caused by premature destruction of red blood cells. Naphthalene exposure can cause hemolysis and resulting anemia.
Anthracene: A polycyclic aromatic hydrocarbon composed of three linearly fused benzene rings. Anthracene extends the fused-ring series beyond naphthalene’s two rings.

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