Benzofuran
CAS number: 271-89-6
2,3-Benzofuran is a colorless, sweet-smelling, oily liquid made by processing coal into coal oil. It may also be formed during other uses of coal or oil. 2,3-Benzofuran is not used for any commercial purposes, but the part of the coal oil that contains 2,3-benzofuran is made into a plastic called coumarone-indene resin.
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A: When benzofuran is used instead of benzo[b]thiophene, the reaction becomes highly exothermic and leads to the formation of unidentified byproducts, presumably via a peroxide intermediate. This indicates that the heteroatom (sulfur in benzo[b]thiophene) plays a crucial role in facilitating the chlorination reaction.