Benzothiophene
Encyclopedia
Benzothiophene is an aromatic 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...

 with a molecular formula C8H6S and an odor similar to naphthalene
Naphthalene
Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...

 (mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite
Lignite
Lignite, often referred to as brown coal, or Rosebud coal by Northern Pacific Railroad,is a soft brown fuel with characteristics that put it somewhere between coal and peat...

 tar. Benzothiophene has no household use. It is used primarily in industry and research.

Being a heterocyclic compound, benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene
Raloxifene
Raloxifene is an oral selective estrogen receptor modulator that has estrogenic actions on bone and anti-estrogenic actions on the uterus and breast...

, zileuton
Zileuton
Zileuton is an orally active inhibitor of 5-lipoxygenase, and thus inhibits leukotrienes formation. Zileuton is used for the maintenance treatment of asthma. Zileuton was introduced in 1996 by Abbott Laboratories and is now marketed in two formulations by Cornerstone Therapeutics Inc. under the...

, and sertaconazole
Sertaconazole
Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot....

. It is also used in the manufacturing of dyes such as thioindigo.

Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.
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