Tetrahydrothiophene

Tetrahydrothiophene is a heterocyclic organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 consisting of a five-membered ring containing four carbon

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 atoms and a sulfur

Sulfur

Sulfur or sulphur is the chemical element with atomic number 16. In the periodic table it is represented by the symbol S. It is an abundant, multivalent non-metal. Under normal conditions, sulfur atoms form cyclic octatomic molecules with chemical formula S8. Elemental sulfur is a bright yellow...

 atom. It is the saturated

Saturation (chemistry)

In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...

 analog of thiophene

Thiophene

Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a flat five-membered ring, it is aromatic as indicated by its extensive substitution reactions. Related to thiophene are benzothiophene and dibenzothiophene, containing the thiophene ring fused with one and two benzene...

. It is a volatile, clear, colorless liquid with a strong unpleasant odor

Odor

An odor or odour is caused by one or more volatilized chemical compounds, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction. Odors are also commonly called scents, which can refer to both pleasant and unpleasant odors...

.

Because of its smell, tetrahydrothiophene is occasionally used as an odorant in natural gas

Natural gas

Natural gas is a naturally occurring gas mixture consisting primarily of methane, typically with 0–20% higher hydrocarbons . It is found associated with other hydrocarbon fuel, in coal beds, as methane clathrates, and is an important fuel source and a major feedstock for fertilizers.Most natural...

, in place of the more common ethanethiol

Ethanethiol

Ethanethiol is an organic compound with the formula CH3CH2SH. It consists of an ethyl group, CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with S instead of O. The presence of S leads to many different properties, most notably the infamous odour of EtSH...

. It is also used as a solvent

Solvent

A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

, as an insecticide

Insecticide

An insecticide is a pesticide used against insects. They include ovicides and larvicides used against the eggs and larvae of insects respectively. Insecticides are used in agriculture, medicine, industry and the household. The use of insecticides is believed to be one of the major factors behind...

, and as a moth repellent

Insect repellent

An insect repellent is a substance applied to skin, clothing, or other surfaces which discourages insects from landing or climbing on that surface. There are also insect repellent products available based on sound production, particularly ultrasound...

. It is an intermediate in the preparation of the solvent sulfolane

Sulfolane

Sulfolane is a clear, colorless liquid commonly used in the chemical industry as an extractive distillation solvent or reaction solvent. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene...

, which is produced by the oxidation of tetrahydrothiophene. It is also used as an electrolyte

Electrolyte

In chemistry, an electrolyte is any substance containing free ions that make the substance electrically conductive. The most typical electrolyte is an ionic solution, but molten electrolytes and solid electrolytes are also possible....

 for lithium batteries

Lithium battery

Lithium batteries are disposable batteries that have lithium metal or lithium compounds as an anode. Depending on the design and chemical compounds used, lithium cells can produce voltages from 1.5 V to about 3.7 V, over twice the voltage of an ordinary zinc–carbon battery or alkaline battery...

.

As an odorant, it has numerous advantages against ethanethiol. It is not corrosive to the gas pipes and valves, it does not cause habitual deactivation of sense of smell, and it does not cause irritant responses of coughing, tears, and headache. It is regarded to be an ideal gas indicator in use.

This compound is used as an easily-displaceable ligand in chloro(tetrahydrothiophene)gold(I)

Chloro(tetrahydrothiophene)gold(I)

Chlorogold a coordination complex of gold. Like the dimethyl sulfide analog, this compound is used as a convenient entry point to gold chemistry. The tetrahydrothiophene ligand is labile and is readily substituted with other stronger ligands.-Preparation:This compound is not commonly available...

.