7342-82-7

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-1-benzothiophene is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
3-Bromo-1-benzothiophene is used as a building block in the synthesis of complex organic molecules, particularly those containing the benzo[b]thiophene moiety. Its reactivity in the Suzuki-Miyaura reaction makes it a valuable component in the creation of new chemical entities.
Used in Antifungal Applications:
3-Bromo-1-benzothiophene is used as a starting material for the synthesis of synthetic di(hetero)arylamines, which exhibit antifungal activity. These compounds can be used in the development of new antifungal agents to combat various fungal infections.
Used in Material Science:
3-Bromo-1-benzothiophene may be used in the synthesis of (benzo[b]thiophen-3-yl)trimethylstannane, which can be further utilized in the development of new materials with unique properties, such as improved conductivity or enhanced stability.

InChI:InChI=1/C8H5BrS/c9-7-5-10-8-4-2-1-3-6(7)8/h1-5H

Upstream product

• 95-15-8 Benzo[b]thiophene 
• 462-80-6 benzyne 
• 3141-26-2 3,4-dibromothiophene 
• 128-08-5 N-Bromosuccinimide 
• 415680-02-3 trimethyl{[2-(methylsulfanyl)phenyl]ethynyl}silane 
• 6287-82-7 2,3-dibromobenzo[b]thiophene 
• 5381-25-9 benzo[b]thiophene-3-carboxylic acid 
• 130-03-0 thioindoxyl 
• 33775-94-9 2-(methylthio)iodobenzene 

Downstream Products

• 33880-37-4 3-(1-piperidinyl)benzothiophene 
• 40584-57-4 2-(piperidin-1-yl)-1-benzothiophene 
• 95-15-8 Benzo[b]thiophene 
• 16957-97-4 3-bromobenzothiophene S,S-dioxide 
• 17402-78-7 3-bromo-2-nitro-1-benzothiophene 
• 496-31-1 benzo[b]-2,3-dihydrothiophen-2-one 
• 1128-05-8 3-acetylbenzothiophene 
• 35472-34-5 1-(benzo[b]thiophen-3-yl)-2,2,2-trifluoroethan-1-one 
• 99661-12-8 benzoyl-2 bromo-3 benzothiophene 
• 99661-17-3 anisoyl-2 bromo-3 benzothiophene 
• 81471-21-8 3-Benzothienylthiosalicylsaeure 
• 99661-07-1 acetyl-2 bromo-3 benzothiophene 
• 27884-09-9 2-(4-methoxyphenyl)benzo[b]thiophene 
• 25664-47-5 2-(4-methylphenyl)benzo[b]thiophene 

Relevant academic research and scientific papers

Selective synthesis, structure and oxidation properties of isomeric 1,4-dithiins fused to two benzo[b]thiophenes

Two novel isomers of 1,4-dithiins fused to two benzo[b]thiophenes on both sides were obtained by selective synthetic methods via the corresponding sulfides. The crystal structures of two dithiins were determined by X-ray crystallographic analyses. Examination of oxidation properties of the dithiins showed interesting results by CV measurement. The ESR spectra of chemically oxidized dithiins indicated formation of stable radical cations.

A room-Temperature phosphorescent polymer film containing a molecular web based on one-dimensional chiral stacking of a simple luminophore

We propose a new approach for a totally organic, room-Temperature phosphorescent system with a lifetime on the order of milliseconds, which is achieved by promotion of the one-dimensional chiral stacking of a simple, small fluorophore in a solution state. The versatility of this system is highlighted by its good applicability to the fabrication of a phosphorescent polymer film. This paper demonstrates the first example of a room-Temperature phosphorescent polymer film prepared with our methodology.

Syntheses and properties of nine-ring-fused linear thienoacenes

π-Extended nine-ring-fused linear thienoacenes 1a-c with internal thieno[3,2-b;4,5-b′]dithiophene substructures were synthesized. Their optical and electrochemical properties were investigated. Thin-film transistor characteristics showed all compounds displayed high device reproducibility and nearly no dependence on substrate temperatures. The highest performance was observed for 1c-based devices with mobility up to 1.0 cm2/Vs and current on/off ratio of 107, whereas the maximum mobility was 0.5 cm2/Vs for 1b and 0.011 cm2/Vs for 1a.

Structure-property relationships of benzo[2,1-b:3,4-b']bis[1]benzothiophenes for organic field effect transistors

A series of novel benzo[2,1-b:3,4-b']bis[1]-benzothiophene (BBBT) derivatives with different side-chains were synthesized and characterized. And their mobility properties were evaluated based on their active layers in OFETs devices. By means of simple thermal annealing, the devices based on BBBT-4 and BBBT-6 exhibited typical p-type FETs behavior with average hole mobilities of 0.28 and 0.124 cm2 V?1 s?1, respectively. Furthermore, the structure-property relationships of these semiconductors were also investigated by XRD and AFM.

Benzothieno [3, 2-b] benzothiophene-like hole transport material and preparation method and application thereof

The invention discloses a benzothieno [3, 2-b] benzothiophene-like hole transport material as well as a preparation method and application thereof. According to the invention, a benzo five-membered ring [3, 2-b] benzo five-membered ring (BXBY)-based hole

Thermally activated delayed fluorescent deep blue light material and preparation method thereof with organic electroluminescent device

The present invention discloses a thermal activation delayed fluorescent deep blue light material and preparation method thereof and an organic electroluminescent device, the thermal activation delayed fluorescent deep blue light material having the follo

Flexible on-site halogenation paired with hydrogenation using halide electrolysis

Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.

Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.

Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons

Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.

Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides

An enantioselective dearomative 1,3-dipolar cycloaddition of 2-nitrobenzothiophenes and isatin-derived azomethine ylides with a bifunctional hydrogen-bonding thiourea catalyst was established, giving polyheterocyclic compounds in excellent results (up to 99% yield, >20:1 dr for all cases and up to 99% ee). The enantioselectivity could be reversed by the bifunctional hydrogen-bonding squaramide catalyst containing the same chiral source as in the thiourea catalyst. DFT calculations revealed the origin of the observed stereochemistry and the reversal of enantioselectivity.