Thiolane

Thiolane is a five-membered heterocyclic organic compound containing one sulfur atom. Its chemical formula is C4H8S. It is also known by its systematic name, tetrahydrothiophene. Thiolane is a saturated cyclic sulfide, meaning it is composed of a ring of four carbon atoms and one sulfur atom, with all atoms in the ring being singly bonded. It is a colorless liquid with a distinctive, strong, and unpleasant odor, similar to other volatile sulfur compounds. This strong odor is often used as an additive to natural gas to make leaks detectable, as pure natural gas is odorless.

Thiolane is miscible with many organic solvents and has limited solubility in water. Its chemical properties are characteristic of sulfides, including its ability to undergo oxidation to form sulfoxides and sulfones. Thiolane can also participate in reactions involving electrophilic attack at the sulfur atom. It can be prepared through various synthetic routes, often involving cyclization reactions of sulfur-containing precursors. Due to its use as an odorant in natural gas, it is produced and handled on an industrial scale. It is also found naturally in some petroleum fractions.