270-82-6

Usage

Uses

Used in Pharmaceutical Industry:
Benzo[c]thiophene is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of novel drugs with potential applications in treating a wide range of diseases, including cancer, neurological disorders, and cardiovascular conditions.
Used in Chemical Industry:
In the chemical industry, Benzo[c]thiophene serves as a valuable building block for the production of various specialty chemicals, such as dyes, pigments, and additives. Its versatile chemical properties enable it to be used in the synthesis of a wide array of compounds with diverse applications.
Used in Material Science:
Benzo[c]thiophene's unique structure and properties make it an attractive candidate for the development of new materials with specific characteristics. It can be used in the design and synthesis of advanced materials for applications in electronics, optoelectronics, and energy storage devices.
Used in Agrochemical Industry:
Benzo[c]thiophene can also be utilized in the agrochemical industry as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique chemical properties can be exploited to develop novel compounds with improved efficacy and selectivity.

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 4112, 1966 DOI: 10.1021/ja00969a052

InChI:InChI=1/C8H6S/c1-2-4-8-6-9-5-7(8)3-1/h1-6H

Upstream product

• 3533-72-0 syn- and anti-cis-8-thiabicyclo<4.3.0>non-3-ene 8-oxide 
• 608-23-1 3-chloro-o-xylene 
• 612-12-4 o-Xylylene dichloride 
• 41383-84-0 1,2-bis(mercaptomethyl)benzene 
• 91-13-4 α,α'-dibromo-o-xylene 
• 95-47-6 o-xylene 
• 2471-92-3 1,3-Dihydrobenzothiophen 
• 131193-77-6 1,3-Dihydro-2-methoxybenzothiophenium-trifluoromethansulfonat 

Downstream Products

• 119438-92-5 9,10-diphenyl-9,10-dihydro-9,10-episulfido-anthracene 

Relevant academic research and scientific papers

Benzo[c]thiophene-C60 diadduct: An electron acceptor for p-n junction organic solar cells harvesting visible to near-IR light

We synthesized a new 56-π-electron fullerene derivative through a Diels-Alder cycloaddition of benzo[c]thiophene that featured a relatively low temperature, closer to stoichiometric use of the diene, and easy product purification. The 56-π-electron benzo[c]thiophene diadduct (BTCDA) has a LUMO energy level of 0.09 to 0.18 eV higher than that of 58-π-electron fullerenes, and therefore, the BTCDA-based organic photovoltaic device exhibited a higher open-circuit voltage and power-conversion efficiency (PCE). When used with a binary-donor system, including visible-light-harvesting tetrabenzoporphyrin (BP) and near-IR-harvesting titanyl phthalocyanine (TiOPc), the device had a PCE that was 1.5-3 times higher (2.8 %) than that for devices with BP or TiOPc alone because the binary-donor device can utilize light between λ=350 and 950 nm. Copyright

Air-Stable Benzo[ c]thiophene Diimide n-Type π-Electron Core

In this paper, the molecular design of the first deep-lowest unoccupied molecular orbital (LUMO) level diimide π-electron core, benzo[c]thiophene diimide (BTDI), as a novel n-type organic semiconductor was determined. An original synthetic sequence was de

Semiconductor material and preparation methods and applications thereof

The invention discloses a semiconductor material and preparation methods and applications thereof. A molecular structure general formula of the material is one of the formulas shown in the description. The semiconductor material provided by the invention

HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are thiophene compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

Synthesis and optical properties of 1,1-binaphthyl-thiophene alternating copolymers with main chain chirality

A series of axially chiral 1,1-binaphthyl-thiophene copolymers were synthesized by Migita-Kosugi-Stille polycondensation and electrochemical polymerization. The polymers exhibit circular dichroism not only in the ultraviolet region but also in the visible region, both in solution and film states. Optical and electrochemical properties of the polymers are in good agreement with theoretical results obtained by density functional theory calculations. Although effective conjugation of the polymers was cleaved at the orthogonally oriented two naphthalene rings in the 1,1-binaphthyl unit, the electrochemically synthesized polymer film shows good electrochemical redox behavior with repeatable changes in optical absorption and circular dichroism. The changes in circular dichroism may reflect a change in the dihedral angle of the binaphthyl unit caused by reorientation of conjugated main chains between oxidized and neutral states. The Royal Society of Chemistry 2012.

Intramolecular condensation of 1,2-C6H4(CH 2RH)2 (R = O, S, and NH) to yield heterocyclic compounds over halide-cluster catalysts

1,2-Benzenedimethanol was reacted under a helium stream in the presence of [(Nb6Cl12)Cl2(H2O) 4]·4H2O supported on silica gel. When the temperature was raised above 200 °C, catalytic activity of the cluster for cyclization appeared, yielding 1,3-dihydroisobenzofuran in 91% selectivity at 350 °C. The corresponding halide clusters of tantalum and tungsten also catalyzed the reaction. cis-1,2-Cyclohexanedimethanol and 1,4-butanediol exclusively produced the corresponding furans. 1,2-Benzenedimethanamine and 1,2-benzenedimethanethiol selectively afforded isoindoline and 1,3-dihydrobenzo[c]thiophene, respectively.

Thiophene derivative and organic electroluminescent element

The present invention provides a thiophene derivative useful for a material for forming an organic positive hole layer of an organic EL element excellent in light emitting efficiency, water resistance or the like, a polymer having the thiophene derivative

Structure and Reactivity of Isoannulated Heterocyclic Systems with 4n-? and (4n + 2)-? Electrons, XVIII. - Benzothiophenes with Symmetric Structure: Modified and Optimized Preparations by the S-Oxide Route

Benzothiophenes (15) with symmetric structure have been prepared efficiently from 1,3-dihydrobenzothiophene 2-oxides (9) by reaction with aluminium oxide, by O-acylation with trifluoroacetic anhydride, or O-alkylation with methyl trifluoromethanesulfonate.The aromatization of the S-oxides 9 is achieved by O-functionalization, subsequent elimination, and consecutive deprotonation.