tetrahydrofurans

Tetrahydrofurans are a class of saturated heterocyclic compounds that share a common five‑membered ring containing one oxygen atom. The parent compound, tetrahydrofuran (THF), also known as oxolane, has the formula C4H8O and serves as a versatile solvent and building block in organic synthesis. Substituted derivatives arise when ring carbons are replaced by alkyl or aryl groups, creating a family of tetrahydrofurans with varied properties and applications.

THF rings are relatively stable but can exhibit reactivity characteristic of ethers. The parent THF is a colorless, volatile liquid with moderate polarity and wide solvent compatibility. It is prone to slow peroxide formation when stored in the presence of air and light, especially if stabilizers or inhibitors are not used; precautions include storage in closed containers and testing for peroxides before distillation.

Industrial production of THF typically involves hydrogenation of furan, which is derived from furfural, itself obtained from agricultural feedstocks. The resulting THF and its derivatives are used broadly as solvents in polymerization, coatings, and pharmaceutical synthesis. A notable derivative is 2-methyl tetrahydrofuran (2-MeTHF), a greener, bio-based solvent that can replace THF in some applications due to its higher boiling point and improved safety profile. Tetrahydrofuran rings also occur as structural motifs in natural products and pharmaceuticals, and as units in polymers such as poly(tetramethylene ether) glycol, a key diol for polyurethane production.

Safety considerations include flammability and the risk of peroxide formation; appropriate storage, inhibitors, and handling procedures are important in laboratory and industrial settings.