Tetrahydrofuran

Ball-and-stick model of tetrahydrofuran. The red ball is oxygen, black balls are carbon, and white balls are hydrogen.

Tetrahydrofuran (abbreviated THF, systematic name oxolane) is an organic compound made of hydrogen, carbon, and oxygen. It has the chemical formula C
4H
8O. It is a cyclic compound and an ether. Because the cycle contains an oxygen atom, it is heterocyclic. It is used as a solvent in organic chemistry and to make some polymers.

Preparation

Tetrahydrofuran is mostly made by the dehydration of 1,4-butanediol. A strong acid (usually sulfuric acid) reacts with two equivalents of alcohol, removing a water molecule and connecting the alcohol groups together into an ether. Making a cyclic ether like THF needs both alcohol equivalents to be on one molecule (a diol).

Uses

Tetrahydrofuran is an important solvent, used in many chemical reactions where water could damage the chemicals used. It is similar to diethyl ether but has a higher boiling point.

Ring-opening polymerization of THF makes polytetrahydrofuran, a polymeric diol used to make some kinds of synthetic fiber and polyurethane.

Related compounds

It has the same chemical formula as butanone, another solvent. They are structural isomers.

Tetrahydrofuran Media

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  Structure of VCl3(thf)3

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  Tetrahydrofuran peroxide formation

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  Chemical structure of annonacin, an acetogenin.

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  Eribulin (brand name: Halaven), a commercial THF-containing anticancer drug.