85553-43-1

Basic information

• Product Name: 2-(3-Methylphenyl)thiophene
• Synonyms: 2-(3-Methylphenyl)thiophene
• CAS NO: 85553-43-1
• Molecular Formula: C₁₁H₁₀S
• Molecular Weight: 174.26
• Product Categories: API intermediates
• Mol File: 85553-43-1.mol

Chemical Properties

• Boiling Point: 264 °C at 760 mmHg
• Flash Point: 82.3 °C
• Appearance: /
• Density: 1.085 g/cm³
• Vapor Pressure: 0.0163mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 2-(3-Methylphenyl)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Methylphenyl)thiophene(85553-43-1)
• EPA Substance Registry System: 2-(3-Methylphenyl)thiophene(85553-43-1)

Safety Data

• Hazardous Substances Data: 85553-43-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Methylphenyl)thiophene is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new medicinal compounds with potential therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(3-Methylphenyl)thiophene is utilized as a building block for the creation of various agrochemicals, leveraging its chemical structure to enhance the effectiveness of these products in agricultural applications.
Used in Dye Production:
2-(3-Methylphenyl)thiophene is employed as a component in the production of dyes, capitalizing on its aromatic properties to create dyes with specific color characteristics and stability.
Used in Optoelectronic Materials:
2-(3-Methylphenyl)thiophene is used as a precursor in the development of optoelectronic materials due to its electronic and optical properties, which are beneficial for applications in light-emitting diodes (LEDs), solar cells, and other optoelectronic devices.
Used in Material Science:
2-(3-Methylphenyl)thiophene is utilized in material science for the research and development of organic semiconductors and electronic devices, taking advantage of its unique electronic properties to improve the performance of these technologies.

InChI:InChI=1/C11H10S/c1-9-4-2-5-10(8-9)11-6-3-7-12-11/h2-8H,1H3

Upstream product

• 3437-95-4 2-Iodothiophene 
• 17933-03-8 m-tolylboronic acid 
• 6165-68-0 thiophene boronic acid 
• 625-95-6 3-Iodotoluene 
• 1003-09-4 2-bromothiophene 
• 28987-79-3 m-tolylmagnesium bromide 
• 188290-36-0 thiophene 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 591-17-3 meta-bromotoluene 
• 108-88-3 toluene 
• 96-43-5 2-thienyl chloride 
• 2786-07-4 2-thienyl lithium 
• 1009-01-4 2-methylphenyl methanesulfonate 

Downstream Products

• 85553-44-2 3-(2-thienyl)benzyl bromide 
• 1168153-94-3 4-oxo-4-[5-(m-tolyl)-2-thienyl]butanoic acid 
• 184035-74-3 N-(4-bromo-3-methyl-5-isoxazolyl)-5-(3-tolyl)thiophene-2-sulfonamide 
• 184040-70-8 2-chlorosulfonyl-5-(3-tolyl)thiophene 

Relevant articles and documents

Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex

The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.

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.

Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols

A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.

Non-Directed Cross-Dehydrogenative (Hetero)arylation of Allylic C(sp3)?H bonds enabled by C?H Activation

Herein, we report the selective, non-directed and cross-dehydrogenative coupling of allylic C(sp3)?H bonds with C(sp2)?H bonds of (hetero)arenes. The methodology employs olefins and (hetero)arenes which are abundantly available chemical feedstocks, and could be applied in late-stage functionalization reactions of pharmaceuticals. Furthermore, the system exclusively delivers the allylic C?C coupling products highlighting the preservation of the olefin substitution pattern for further derivatization.

Accessing Heterobiaryls through Transition-Metal-Free C-H Functionalization

Herein we report a transition-metal-free synthetic protocol for heterobiaryls, one of the most important pharmacophores in the modern drug industry, employing a new multidonor phenalenyl (PLY)-based ligand. The current procedure offers a wide substrate scope (24 examples) with a low catalyst loading resulting in an excellent product yield (up to 95%). The reaction mechanism involves a single electron transfer (SET) from a phenalenyl-based radical to generate a reactive heteroaryl radical. To establish the mechanism, we have isolated the catalytically active SET initiator, characterizing by a magnetic study.

Modular synthesis of heptaarylindole

The first synthesis of heptaarylindole (HAI) has been accomplished using a coupling/ring transformation strategy. Four readily prepared modular units (diarylthiophenes, 2-arylaziridines, arylboronic acids, and arylalkynes) were joined together to provide

3-(1,1-dimethyl-2-aryl-indenyl)dicyclohexylphosphine and preparation method thereof

The invention aims at exploring a synthetic phosphine ligand, and provides 3-(1,1-dimethyl-2-aryl-indenyl)dicyclohexylphosphine and a preparation method thereof.

2-Aryl-indenylphosphine ligands: Design, synthesis and application in Pd-catalyzed Suzuki-Miyaura coupling reactions

A focused library of phosphine ligands was constructed for structural optimization. The catalyst can be used to perform the Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl chlorides.

Biarylalkyl Carboxylic Acid Derivatives as Novel Antischistosomal Agents

Parasitic platyhelminths are responsible for serious infectious diseases, such as schistosomiasis, which affect humans as well as animals across vast regions of the world. The drug arsenal available for the treatment of these diseases is limited; for example, praziquantel is the only drug currently used to treat ≥240 million people each year infected with Schistosoma spp., and there is justified concern about the emergence of drug resistance. In this study, we screened biarylalkyl carboxylic acid derivatives for their antischistosomal activity against S. mansoni. These compounds showed significant influence on egg production, pairing stability, and vitality. Tegumental lesions or gut dilatation was also observed. Substitution of the terminal phenyl residue in the biaryl scaffold with a 3-hydroxy moiety and derivatization of the terminal carboxylic acid scaffold with carboxamides yielded compounds that displayed significant antischistosomal activity at concentrations as low as 10 μm with satisfying cytotoxicity values. The present study provides detailed insight into the structure–activity relationships of biarylalkyl carboxylic acid derivatives and thereby paves the way for a new drug-hit moiety for fighting schistosomiasis.

Synthesis of functionalized 2-arylthiophenes with triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium catalysis

Atom-efficient cross-coupling reactions of functionalized 2-bromo- and 2-iodothiophenes have been demonstrated using triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium-catalyzed conditions. These couplings with various functionalized triarylbismuths proceeded smoothly to afford the corresponding functionalized 2-arylthiophenes in high yields. Georg Thieme Verlag Stuttgart · New York.