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
• Article Data: 17

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

General Description

2-(3-Methylphenyl)thiophene is a chemical compound with the molecular formula C11H10S. It is a thiophene derivative, which is a five-membered aromatic ring containing four carbon atoms and one sulfur atom. 2-(3-Methylphenyl)thiophene is commonly used in the synthesis of various organic compounds and pharmaceuticals. It is known for its strong aromatic odor and is often used as a building block in the production of agrochemicals, dyes, and optoelectronic materials. Additionally, 2-(3-Methylphenyl)thiophene has potential applications in the field of material science, as it exhibits interesting electronic and optical properties, making it useful in the development of organic semiconductors and electronic devices.

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

Upstream product

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

Downstream Products

• 38401-69-3 5-(3-methylphenyl)-2-thiophenecarboxaldehyde 
• 184040-70-8 2-chlorosulfonyl-5-(3-tolyl)thiophene 
• 184035-74-3 N-(4-bromo-3-methyl-5-isoxazolyl)-5-(3-tolyl)thiophene-2-sulfonamide 
• 85553-44-2 3-(2-thienyl)benzyl bromide 
• 1168153-94-3 4-oxo-4-[5-(m-tolyl)-2-thienyl]butanoic acid 

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.

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.

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