Benzothiophene Numbering on:
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Benzothiophene is an
In the presence of a gold catalyst, a more complex 2,3-disubstituted benzothiophene can be synthesised.
aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
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 Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...
(mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite
Lignite (derived from Latin ''lignum'' meaning 'wood'), 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 ...
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 ...
, 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 Laborato ...
, 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 (pharmaceutical), cream to treat skin infections such as athlete's foot.
It is also available in a ...
, 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 Car ...
. 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, replacing two NH groups with two sulfur atoms to create a shade of pink.
Thioindigo is generate ...
.
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 eithersodium sulfide
Sodium sulfide is a chemical compound with the formula Na2 S, or more commonly its hydrate Na2S·9 H2O. Both the anhydrous and the hydrated salts are colorless solids, although technical grades of sodium sulfide are generally yellow to brick red ...
or potassium sulfide
Potassium sulfide is an inorganic compound with the formula K2 S. The colourless solid is rarely encountered, because it reacts readily with water, a reaction that affords potassium hydrosulfide (KSH) and potassium hydroxide (KOH). Most commonl ...
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 (), with the oxygen atom replaced by sulfur atom (as implied by the '' thio-'' prefix). The properties of urea and thiourea differ s ...
can be used as a reagent in place of sodium sulfide or potassium sulfide.
In the presence of a gold catalyst, a more complex 2,3-disubstituted benzothiophene can be synthesised.
References
{{Simple aromatic rings Simple aromatic rings