11095-43-5

Basic information

• Product Name: benzothiophene
• Synonyms: 1-benzothiophene;2,3-Benzothiophene
• CAS NO: 11095-43-5
• Molecular Formula: C8H6S
• Molecular Weight: 134.1982
• EINECS: 202-395-7
• Mol File: 11095-43-5.mol
• Article Data: 149

Chemical Properties

• Melting Point: 28-32℃
• Boiling Point: 221 °C at 760 mmHg
• Flash Point: 62 °C
• Appearance: /
• Density: 1.187 g/cm³
• Vapor Pressure: 0.163mmHg at 25°C
• Refractive Index: 1.675
• Water Solubility: insoluble
• CAS DataBase Reference: benzothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: benzothiophene(11095-43-5)
• EPA Substance Registry System: benzothiophene(11095-43-5)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Hazardous Substances Data: 11095-43-5(Hazardous Substances Data)

Usage

Description

Benzothiophene is a heterocyclic compound characterized by a fused benzene and thiophene ring structure. It is a colorless liquid with a distinct odor and is recognized for its applications in various industries, including pharmaceuticals, agrochemicals, and dyes. Benzothiophene is also found in coal tar and is a byproduct of coal combustion. However, it is important to note that it possesses mutagenic and carcinogenic properties, and exposure to benzothiophene is associated with potential health risks. Therefore, it is crucial to handle and dispose of benzothiophene safely and responsibly.

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 articles and documents

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.

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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.

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.

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

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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

AN UNUSUAL CONVERSION OF 2,2,3,3-TETRAFLUORO-2,3-DIHYDROBENZOTHIOPHENE WITH LITHIUM ALUMINUM HYDRIDE

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The preparation of (Z)-2-lithio-ortho-styryllithium via an ortho-directed lithiation

Lithiation of (Z)-2-lithiostyrene with t-butyllithium/TMEDA pentane led directly to (Z)-2-lithio-ortho-styryllithium. subsequent treatment of this dilithio compound with difunctional electrophiles allowed the preparation of a variety of benzoheteroles.

High-temperature synthesis of thiophene from bis(2-chloroethyl) sulfide

Gas-phase reaction of bis(2-chloroethyl) sulfide (Yperite) with acetylene at 550-700°C leads to formation of thiophene in 45% yield, the conversion of the initial sulfide being complete. The yield of thiophene reaches 63-68% in the thermolysis of a mixture of acetylene, bis(2-chloroethyl) sulfide, and lower organic disulfides.

Photolysis of β-(o-Methylthiophenyl)vinyl Bromides. A Versatile Synthesis of Benzothiophens

Exclusive cyclization in photolysis of β-(o-methylthiophenyl)vinyl bromides to give benzothiophens is described.

Ceramic boron carbonitrides for unlocking organic halides with visible light

Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is

Site-Selective Silver-Catalyzed C-H Bond Deuteration of Five-Membered Aromatic Heterocycles and Pharmaceuticals

Catalytic methods for the direct introduction of hydrogen isotopes into organic molecules are essential to the development of improved pharmaceuticals and to the alteration of their absorption, distribution, metabolism, and excretion (ADME) properties. However, the development of homogeneous catalysts for selective incorporation of isotopes in the absence of directing groups under practical conditions remains a long-standing challenge. Here, we show that a phosphine-ligated, silver-carbonate complex catalyzes the site-selective deuteration of C-H bonds in five-membered aromatic heterocycles and active pharmaceutical ingredients that have been resistant to catalytic H/D exchange. The reactions occur with CH3OD as a low-cost source of the isotope. The silver catalysts react with five-membered heteroarenes lacking directing groups, tolerate a wide range of functional groups, and react in both polar and nonpolar solvents. Mechanistic experiments, including deuterium kinetic isotope effects, determination of kinetic orders, and identification of the catalyst resting state, support C-H bond cleavage from a phosphine-ligated, silver-carbonate intermediate as the rate-determining step of the catalytic cycle.