Thiophene

Thiophene is a heterocyclic compound with the formula C4H4S. It is a colorless liquid with a benzene-like odor. Thiophene is the simplest member of the thiophene family, which also includes compounds such as bithiophene, terthiophene, and polythiophene. Thiophene is used as a building block in the synthesis of many pharmaceuticals and agrochemicals.

History

Thiophene was discovered in 1883 by the Swiss chemist A. von Baeyer, who prepared it by the action of heat on a mixture of succinic and thionic acids.

Structure and bonding

Thiophene has a five-membered ring, which consists of four carbon atoms and one sulfur atom. The sulfur atom is in the same plane as the carbon atoms, and the molecule is planar. The sulfur atom contributes six electrons to the pi system, making thiophene aromatic.

Synthesis

Thiophene can be synthesized by various methods, including the Gattermann reaction, the Paal-Knorr synthesis, and the Gewald reaction. The most common industrial method for the production of thiophene is the vapor-phase reaction of 1,3-butadiene and sulfur.

Applications

Thiophene is used as a building block in the synthesis of many pharmaceuticals and agrochemicals. It is also used in the production of dyes and plastics.

Safety

Thiophene is harmful if swallowed, inhaled, or comes into contact with skin. It is also flammable.

See also

• Furan
• Pyridine
• Pyrrole

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