Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

Production

Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethyl phenol.

Laboratory methods

Benzofurans can be prepared by various methods in the laboratory. Notable examples include: *''O''-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation.

* Perkin rearrangement, where a coumarin is reacted with a hydroxide: : * Diels–Alder reaction of nitro vinyl furans with various dienophiles: : * Cycloisomerization of alkyne ortho-substituted phenols: :

Related compounds

* Substituted benzofurans * Dibenzofuran, an analog with a second fused benzene ring. * Furan, an analog without the fused benzene ring. * Indole, an analog with a nitrogen instead of the oxygen

atom Atoms are the basic particles of the chemical elements. An atom consists of a atomic nucleus, nucleus of protons and generally neutrons, surrounded by an electromagnetically bound swarm of electrons. The chemical elements are distinguished fr ...

. * Benzothiophene, an analog with a sulfur instead of the oxygen

. * Isobenzofuran, the isomer with oxygen in the adjacent position. * Aurone * Thunberginol F

References

{{Authority control IARC Group 2B carcinogens Simple aromatic rings