Benzothiophene Structure on:
[Wikipedia]
[Google]
[Amazon]
Benzothiophene is an
In the presence of a gold catalyst, a more complex 2,3-disubstituted benzothiophene can be synthesised.
aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with a molecular formula C8H6S and an odor similar to naphthalene
Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...
(mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite
Lignite, often referred to as brown coal, is a soft, brown, combustible, sedimentary rock formed from naturally compressed peat. It has a carbon content around 25–35%, and is considered the lowest rank of coal due to its relatively low heat ...
tar. Benzothiophene has no household use. In addition to benzo hiophene, a second isomer is known: benzo hiophene.
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, sold under the brand name Evista among others, is a medication used to prevent and treat osteoporosis in postmenopausal women and those on glucocorticoids. For osteoporosis it is less preferred than bisphosphonates. It is also used to ...
, zileuton
Zileuton (trade name Zyflo) is an orally active inhibitor of 5-lipoxygenase, and thus inhibits leukotrienes (LTB4, LTC4, LTD4, and LTE4) formation, used for the maintenance treatment of asthma. Zileuton was introduced in 1996 by Abbott Laborat ...
, and sertaconazole
Sertaconazole, sold under the brand name Ertaczo among others, is an antifungal medication of the Benzothiophene class. It is available as a cream to treat skin infections such as athlete's foot.
It is also available in a vaginal tablet form. The ...
, and also BTCP
Benocyclidine, also known as benzothiophenylcyclohexylpiperidine (BTCP), is a psychoactive recreational drug of the arylcyclohexylamine class which is related to phencyclidine (PCP). It was first described in a patent application naming Marc C ...
. It is also used in the manufacturing of dyes such as thioindigo
Thioindigo is an organosulfur compound that is used to dye polyester fabric. A synthetic dye, thioindigo is related to the plant-derived dye Indigo dye, indigo, replacing two NH groups with two sulfur atoms to create a shade of pink.
Thioindigo ...
.
Synthesis
Most syntheses of benzothiophene create substituted benzothiophenes as a precursor to further reactions. An example is the reaction of an alkyne-substituted 2-bromobenzene with either sodium sulphide or potassium sulphide to form benzothiophene with an alkyl substitution at position 2.
Thiourea
Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), except that the oxygen atom is replaced by a sulfur atom (as implied by the ''thio-'' prefix); however, the properties of urea ...
can be used as a reagent in place of sodium sulphide or potassium sulphide.
In the presence of a gold catalyst, a more complex 2,3-disubstituted benzothiophene can be synthesised.
References
{{Simple aromatic rings Simple aromatic rings