40133-22-0

Usage

Uses

Used in Organic Synthesis:
2-(4-Bromophenyl)thiophene is used as a building block in the synthesis of various organic compounds due to its unique chemical structure. The presence of the bromine atom allows for further functionalization and modification of the molecule, enabling the creation of a wide range of derivatives with diverse properties and applications.
Used in Pharmaceutical Industry:
2-(4-Bromophenyl)thiophene is used as a scaffold in drug design for the development of new pharmaceuticals. Its ability to interact with biological systems makes it a valuable component in the creation of potential therapeutic agents. Researchers can exploit its unique structure to design drugs targeting specific biological pathways or receptors, leading to the development of novel treatments for various diseases.
Used in Organic Electronics and Optoelectronics:
2-(4-Bromophenyl)thiophene is used in the development of organic electronics and optoelectronic devices due to its unique electronic properties. Its aromatic nature and the presence of the bromine atom contribute to its electronic characteristics, making it suitable for applications such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and organic photovoltaics (OPVs). These devices can benefit from the compound's ability to modulate charge transport and light absorption, leading to improved performance and efficiency.

InChI:InChI=1/C10H7BrS/c11-9-5-3-8(4-6-9)10-2-1-7-12-10/h1-7H

Upstream product

• 3437-95-4 2-Iodothiophene 
• 5467-74-3 4-Bromophenylboronic acid 
• 6165-68-0 thiophene boronic acid 
• 589-87-7 1,4-bromoiodobenzene 
• 188290-36-0 thiophene 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 106-40-1 4-bromo-aniline 
• 1003-09-4 2-bromothiophene 
• 375826-25-8 butyl 4-(4-bromophenyl)-4-oxobutanoate 
• 59099-79-5 4-(4-bromophenyl)-3-butyn-1-ol 
• 106-37-6 1.4-dibromobenzene 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 

Downstream Products

• 83495-24-3 5,5'-Bis-(4-bromo-phenyl)-[2,3']bithiophenyl 
• 37909-88-9 2-([1,1'-biphenyl]-4-yl)thiophene 
• 649569-57-3 methyl 5-(4-bromophenyl)thiophene-2-carboxylate 
• 62404-41-5 [5-(4-bromo-phenyl)-thiophen-2-yl]-acetonitrile 
• 62403-67-2 [5-(4-bromo-phenyl)-thiophen-2-yl]-acetic acid 
• 1255920-11-6 N-(4-(thiophen-2-yl)phenyl)pyrazin-2-amine 
• 1445004-16-9 2-(4-ethynylphenyl)thiophene 
• 35294-37-2 1-(4-(thiophen-2-yl)phenyl)ethanone 
• 183619-15-0 2-bromo-5-(4-bromophenyl)thiophene 
• 38401-70-6 5-(p-Bromophenyl)thiophene-2-carboxaldehyde 

Relevant academic research and scientific papers

Synthesis of Substituted Thiophenes through Dehydration and Heterocyclization of Alkynols

A protocol was described for obtaining a variety of substituted thiophenes with functional potential via metal-free dehydration and sulfur cyclization of alkynols with elemental sulfur (S8) or EtOCS2K in moderate-to-good yields. The method provides the base-free generation of a trisulfur radical anion (S3?-) and its addition to alkynes as an initiator. This research broadens the applications of S3?-in the synthesis of sulfur-containing heterocycles.

Synthesis and fast switching electrochromic properties of conjugated microporous polymers based on carbazole-thiophene derivatives

To study the relationship between chemical structure and switching time of electrochromic polymer materials, four star-shape monomers, 3,6-di(thiophen-2-yl)-9-(4-(thiophen-2-yl)phenyl)-9H-carbazole (M1), 2,7-di(thiophen-2-yl)-9-(4-(thiophen-2-yl)phenyl)-9H-carbazole(M2), 3,6-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-9-(4-(thiophen-2-yl) phenyl)-9H-carbazole(M3) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-9-(4-(thiophen-2-yl)phenyl)-9H-carbazole(M4) were designed and synthesized successfully, their chemical structure were characterized by nuclear magnetic resonance (NMR) and high resolution mass spectrum (HRMS). Their resulting polymer films could be obtained by electropolymerization, all the polymer films showed well-defined electrochemical properties except for PM2, the PM3 and PM4 revealed wider electrochemical response due to the existence of EDOT units. The surface morphology results indicated that all the polymer films consisted of many particles, and PM1 and PM3 showed smaller grain than that of PM2 and PM4 due to the different aggregation structure, which might benefit for the transport of doped ions. Electrochromic kinetic studies confirmed such hypothesis furtherly, PM3 revealed fastest switching time (Tc: 0.72 s and Tb: 0.61 s), the reason could be explained by electrochemical impedance spectroscopy, which indicated that PM3 possessed the smallest charge transfer resistance (Rct) and fastest diffusion coefficient values at the oxidation state. We hope these findings will provide a little effect on designing and synthesizing high performance electrochromic materials and devices.

Fabrication of Graphitic Carbon Nitride-Based Film: An Emerged Highly Efficient Catalyst for Direct C—H Arylation under Solar Light

Photoredox C—H bond formation can proceed in aerobic environment under solar light and has therefore become attractive. Nowadays, different types of expensive novel metal complexes and nanomaterials have been urbanized as photocatalysts for direct C—H bon

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Access to Substituted Thiophenes through Xanthate-Mediated Vinyl C(sp2)-Br Bond Cleavage and Heterocyclization of Bromoenynes

An environmentally sustainable strategy for the chemoselective heterocyclization of bromoenynes through a transition-metal-free sulfuration/cyclization process is reported. Using inexpensive and safe EtOCS2K as a thiol surrogate and tetrabutylphosphonium bromide and H2O as a mixed solvent, the reaction provided a range of substituted thiophenes in moderate to good yields. In addition, 2,3,4,5-tetrasubstituted thiophenes were able to be prepared under mild reaction conditions by electrophilic heterocyclization with NH4I and EtOCS2K in good yields.

Black phosphorus as a metal-free, visible-light-active heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes

Black phosphorus (BP) is for the first time employed as a metal-free, heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes with aryl diazonium salts. The arylated heteroarenes are obtained in moderate to good yields under visible-light illumination, and the protocol is shown to be applicable for the scale-up synthesis.

Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl-heteroaryl compounds

A highly regioselective, carbazole based Electron Donor Acceptor (EDA) catalyzed synthesis of biaryl and aryl-heteroaryl compounds is described. Various indole and carbazole derivatives were screened for the Homolytic Aromatic Substitution (HAS) reaction. Tetrahydrocarbazole (THC) was very efficient for the HAS transformation and proceeded via a complex formation between diazonium salt and electron rich tetrahydrocarbazole. The UV-Vis spectroscopy technique has been used to confirm the complex formation. The in situ generated EDA complex even in a catalytic amount is found to be efficient for the Single Electron Transfer (SET) process without any photoactivation. Biaryl compounds, 2-phenylfuran, 2-phenylthiophene, and 2-phenylpyrrole and bioactive compounds such as dantrolene and canagliflozin have been synthesized in moderate to excellent yields.

Ligand-Less Iron-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane

Iron-catalyzed cross-coupling difluoromethylations of the Grignard reagents with difluoroiodomethane provide various aromatic difluoromethyl products in good yields, not employing sterically demanding ligands. Difluoromethylations proceed within 30 min at -20 °C with 2.0 equiv of the Grignard reagents and FeCl3 or Fe(acac)3 (2.5 mol %). Mechanistic investigations clarify difluoromethyl radical intervention; Fe(0) ate is initially generated. Single-electron transfer from Fe(0) ate to difluoroiodomethane takes place. Recombination with aryl groups gives Ar-CF2Hs. The catalyst can be regenerated by the Grignard reagents.

Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight

Naturally occurring perylenequinonoid pigments (PQPs) have attracted considerable attention owing to their excellent properties of photosensitization. They have been widely investigated as an aspect of photophysics and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C-H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions of substrates was achieved even by a cercosporin-containing supernatant without organic solvent extraction and purification after liquid fermentation. Thus we set up a bridge between microbial fermentation and organic photocatalysis for chemical reactions in a sustainable, environmentally friendly manner.

Phenalenyl Based Aluminum Compound for Catalytic C-H Arylation of Arene and Heteroarenes at Room Temperature

Main group metal based catalysis has been considered to be a cost-effective alternative way to the transition metal based catalysis, due to the high abundance of main group metals in the Earth's crust. Among the main group metals, aluminum is the most abundant (7-8%) in the Earth's crust, making the development of aluminum based catalysts very attractive. So far, aluminum based compounds have been popularly used as Lewis acids in a variety of organic reactions, but chemical transformation demanding a redox based process has never utilized an Al(III) complex as a catalyst. Herein, we tuned the redox noninnocence behavior of a phenalenyl ligand by coupling with Al(III) ion, which subsequently can store the electron upon reduction with K to carry out direct C-H arylation of heteroarenes/mesitylene at ambient temperature. A mechanistic investigation revealed that a three-electron reduced phenalenyl based triradical aluminum(III) complex plays the key role in such catalysis. The electronic structure of the catalytically active triradical species has been probed using EPR spectroscopy, magnetic susceptibility measurements, and electronic structure calculations using a DFT method.