Dibenzofuran
Dibenzofuran is a heterocyclic organic compound with the chemical structure shown at right. It is an aromatic compound that has two benzene rings fused to a central furan ring. All the numbered carbon atoms have a hydrogen atom bonded to each of them. It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained from coal tar, where it exists as a 1% component.
Reactions
Dibenzofuran is thermally robust with a convenient liquid range. These properties, together with its low toxicity, are exploited by the use of DBF as a heat transfer agent.It undergoes electrophilic reactions, such as halogenation and Friedel-Crafts reactions. Reaction of DBF with butyl lithium results in dilithiation.
Dibenzofuran is the precursor to the drug furobufen by Friedel-Crafts reaction with succinic anhydride.
Safety
Dibenzofuran is a relatively non-toxic compound as evidenced by rats being unaffected after a 200-day diet consisting of 0.025 – 0.4% of DBF. The polychlorinated dibenzofurans are however among the potentially toxic dioxins and dioxin-like compounds.Dibenzofuran is cited in the United States Clean Air Act 1990 Amendments -Hazardous Air Pollutants as a volatile hazardous air pollutant of potential concern. The Superfund Amendment Reauthorization Act Section 110 placed dibenzofuran on the revised Agency for [Toxic Substances and Disease Registry] priority list of hazardous substances to be the subject of a toxicological profile. The listing was based on the substance's frequency of occurrence at Comprehensive Environmental Response, Compensation, and Liability Act National Priorities List sites, its toxicity, and/or its potential for human exposure.