11095-43-5

Usage

Uses

Used in Pharmaceutical Industry:
Benzothiophene is used as a precursor for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical sector, benzothiophene is utilized as a starting material for the production of pesticides and other agricultural chemicals. Its chemical properties make it suitable for the creation of effective and targeted agrochemicals.
Used in Dye Industry:
Benzothiophene is employed as a precursor for the synthesis of dyes in the dye industry. Its ability to form a variety of chemical compounds makes it an essential component in the production of different types of dyes.
Used in Coal Tar Production:
Benzothiophene is found in coal tar, which is a byproduct of coal combustion. It contributes to the chemical composition of coal tar and can be extracted and used for various applications.
It is important to emphasize that due to the mutagenic and carcinogenic properties of benzothiophene, strict safety measures and responsible handling practices must be implemented to minimize potential health risks associated with its use.

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

Upstream product

• 110-89-4 piperidine 
• 7342-82-7 3-Bromothianaphthene 
• 100-42-5 styrene 
• 520-72-9 3-hydroxybenzothiophene 
• 825-44-5 benzothiophene-1,1-dioxide 
• 493-57-2 benzo-[b]thiophene-2,3-dione 
• 100-41-4 ethylbenzene 
• 4500-58-7 2-ethylthiophenol 
• 99172-76-6 phenylmercaptoacetaldehyde dimethyl acetal 
• 89978-83-6 2-amino-ω-chloro-styrene 
• 81536-29-0 2-mercaptocinnamic acid 
• 108-98-5 thiophenol 
• 74-86-2 acetylene 
• 420-12-2 thirane 

Downstream Products

• 63471-83-0 4-benzo[b]thiophen-3-yl-4-oxo-butyric acid 
• 74324-97-3 4-(2'-benzothienyl)-4-oxobutanoic acid 
• 501917-82-4 2-(benzo[b]thiophene-2-carbonyl)-benzoic acid 
• 17890-56-1 benzothiophene-2-methanol 
• 22720-67-8 3-(2-methylbenzoyl)benzothiophene 
• 19492-96-7 1-benzo[b]thiophen-3-yl-propan-1-one 
• 6454-03-1 benzo[b]thiophen-3-yl(phenyl)methanone 
• 39620-22-9 3-(4-methoxybenzoyl)benzothiophene 
• 107916-98-3 3-(2-nitro-phenylsulfanyl)-benzo[b]thiophene 
• 858820-12-9 benzo[b]thiophen-3-yl-diphenyl-acetic acid 
• 1128-05-8 3-acetylbenzothiophene 
• 24444-96-0 4-benzo[b]thiophen-3-yl-4-oxo-butyric acid methyl ester 
• 1196-81-2 2-ethylbenzo[b]thiophene 
• 7342-86-1 3-chloro-benzo[b]thiophene 

Relevant academic research and scientific papers

A novel synthesis of benzo[b]thiophene

We report a convenient method of preparation of benzo[b]thiophene, using 2-chlorobenzaldehyde and 2-mercaptoacetonitrile as starting materials. The process comprises two steps, neither of which has been reported previously. The reactions in this work are

Charge-Transfer Complexes of Benzo[b]thiophene with σ- And π-Electron Acceptors

The spectrophotometric properties of the charge-transfer (CT) complexes of benzo[6]thiophene with iodine at 24°C in different solvents such as cychlohexane, carbon tetrachloride, chloroform, dichloromethane, and 1,2-dichloroethane are studied. In addition the spectrophotometric and thermodynamic properties of the CT complexes of benzo[b]thiophene with tetracyanoethylene, chloranil, 2,3-dichloro-5,6-dicyano-p-benzoquinone and 7,7,8,8,-tetracyanoquinodimethane are studied. The results show that the equilibrium and the thermodynamic parameters and the wavelengths of the maximum absorption bands (λmax) of the complexes vary markedly with the solvent. The ionization potential and the donor sites of benzo[b]thiophene are also determined and discussed.

A convenient one-pot preparation of benzo[b] -tellurophenes, - selenophenes, and -thiophenes from o- bromoethynylben zenes

2-Substituted and unsubstituted benzo[b]tellurophenes (3Aa-e) were synthesized in one-pot from o-bromoethynylbenzenes (2) via three steps in good yields. Similarly, benzo[b]-selenophenes (3Ba-e) and -thiophenes (3Ca- e) were also obtained.

Synthesis and reactivities of a highly strained thiophene with two fused four-membered rings, 1,2,4,5-tetahydrodicyclobuta[b,d] thiophene

The successful synthesis of 1,2,4,5-tetrahydrodicyclobuta[b,d]thiophene (1) and its ususually enhanced reactivities because of large ring strain are described. Thus, intramolecular pinacol coupling of diketo sulflde 14, obtainable from 2-bromocyclobutanone and sodium sulfide, with a low-valent titanium reagent affords the thiolane3,4-diol 15 in 36% yield based on the bromo ketone. After conversion of 15 to the bis-methanesulfonate 16 in 66% yield, the latter was treated with potassium tert-butoxide to give 1 nearly quantitatively as a rather thermally stable, colorless, highly sublimative, nicely crystalline compound. Bromine rapidly adds to 1 to give the tetrabromide 21, revealing its olefinic character. Furthermore, 1 undergoes Diels-Alder reaction with tetracyanoethylene at room temperature to afford the adduct 22 in 83% yield. The Diels-Alder reaction with maleic anhydride at room temperature gives the adduct 23 in 87% yield in the endo-exo isomer ratio 5:1, whereas the reaction with excess maleic anhydride in refluxing benzene produces the bisadduct 24 in 84% yield with loss of sulfur. Similar behaviors of 1 toward N-phenylmaleimide were also observed. Flash vacuum pyrolysis of 1 gave benzo[b]thiophene in 16% yield but not the expected radialene 11 or its dimer, superthiophenophane. Other attempts to obtain 11 or to trap it with a dienophile were also unsuccessful.

The role of neighbouring group participation in TTF-mediated 'radical- polar crossover' reactions: Trapping of aliphatic radicals by TTF+.

Trapping of secondary alkyl radicals with tetrathiafulvalenium tetrafluoroborate (TTF+.BF4-) leads to S-alkyltetrathiafulvalenium tetrafluoroborate salts; the solvolysis of such salts is critically dependent on the presence of appropriately sited neighbouring groups.

Desulfurization of thiophene via hydrogen transfer from alkanes on cation-modified H-ZSM5

H-ZSM5, Zn/H-ZSM5, and Co/H-ZSM5 catalyze thiophene desulfurization with high H2S selectivity using propane as the exclusive hydrogen source. Desulfurization rates and selectivities were much higher than at the H2 concentrations present during propane reactions. Zn+2 and Co+2 cations at exchange sites increased desulfurization rates. On H-ZSM5, desulfurization rates and selectivities with propane coreactants (20 kPa) were equivalent to those obtained with >200 kPa H2; on Zn- and Co-exchanged H-ZSM5, the equivalent H2 pressures were 50-100 kPa. These data show that alkane dehydrogenation can be coupled with thiophene hydrogenation on surfaces to increase thiophene desulfurization and propane dehydrogenation rates simultaneously.

1,3-Cycloaddition of Benzyne to Thiophenes

Benzyne, generated from diphenyliodonium-2-carboxylate, reacts with various thiophens by addition to the sulphur and β-carbon to give, after loss of an acetylene moiety, benzothiophenes in low but reproducible yields.

Competitive reactivities of vinylthiyl radicals thermally generated from haloethylenes and hydrogen sulfide

Acetylene and its derivatives have been used for the first time as "traps" for vinylthiyl radicals generated in situ from hydrogen sulfide and haloethylenes in gas-phase processes. The competitive reactivity of the vinylthiyl radicals has been studied at 500-570 °C in the presence of two chemical "traps." The efficiency of chemical "traps" for the vinylthiyl radicals decreases in the following sequence: HC≡CPh > HC≡CH > MeC≡CH > CH2=CHCl. Acetylene is a more efficient "trap" for the vinylthiyl radicals than 1,2-dichloroethylene, from which they have been generated. The β-phenylvinylthiyl radicals generated during cothermolysis of halostyrene-hydrogen sulfide-acetylene component ternary systems undergo first of all intramolecular ring closure to give benzothiophene, which is a thermodynamically favorable system; the reaction of these radicals with acetylene and its derivatives occurs much more slowly than heterocyclization. Phenylacetylene is a more efficient "trap" than acetylene. α-Phenylvinylthiyl radicals mostly react with acetylene to yield 2-phenylthiophene.

Kinetics of bromine-magnesium exchange reactions in heteroaryl bromides

Competition experiments are reported which compare the relative reactivities of bromoheteroarenes toward i-PrMgCl.LiCl in THF at 0 °C

Synthesis, crystal structure and reactivity of η2-thiophyne Ni complexes

The first synthesis and crystal structures of five-membered ring aryne complexes, Ni(dcpe)(η2-thiophyne) and Ni(dcpe)(η2-benzo[b]thiophyne), are described. The aryne fragments retain considerable aromatic character and the two coordi