Dibenzofuran

Error creating thumbnail:

Dibenzofuran-numbering-2D-skeletal.png

Dibenzofuran is a chemical compound with the molecular formula C₁₂H₈O. It is a polycyclic aromatic compound consisting of two benzene rings fused to a central furan ring. Dibenzofuran is a white solid that is insoluble in water but soluble in many organic solvents.

Structure and Properties

Dibenzofuran has a planar structure, which contributes to its stability and its ability to participate in π-π interactions. The compound has a melting point of 81-85°C and a boiling point of 285°C. It is relatively stable under normal conditions but can undergo various chemical reactions typical of aromatic compounds.

Synthesis

Dibenzofuran can be synthesized through several methods, including the dehydration of o-phenylphenol and the cyclization of biphenyl ether. Industrially, it is often produced as a byproduct in the manufacture of other chemicals.

Applications

Dibenzofuran is used in the production of polymers, dyes, and pharmaceuticals. It is also a component in some pesticides and herbicides. Additionally, dibenzofuran derivatives are studied for their potential use in organic electronics and light-emitting diodes (LEDs).

Environmental Impact

Dibenzofuran is a persistent organic pollutant and can be found in the environment as a result of industrial processes and the combustion of organic materials. It is known to be toxic to aquatic life and can accumulate in the food chain.

Health Effects

Exposure to dibenzofuran can occur through inhalation, ingestion, or skin contact. It can cause irritation to the skin, eyes, and respiratory tract. Long-term exposure may lead to more serious health effects, including potential carcinogenicity.

Regulation

Due to its potential health and environmental impacts, dibenzofuran is subject to regulation in many countries. It is included in various environmental protection lists and guidelines to control its release and manage its disposal.

See Also

• Polycyclic aromatic hydrocarbon
• Furan
• Benzene
• Persistent organic pollutant