17595-92-5

Usage

Belongs to the thiophene family

Aromatic compounds with a five-membered ring of four carbon atoms and one sulfur atom

Methoxyphenyl group

Gives a characteristic aromatic and slightly fruity odor

Commonly used as a building block

In the synthesis of various organic compounds and materials (pharmaceuticals, agrochemicals, and organic electronics)

Potential biological activities

Antiviral, antimicrobial, and anti-inflammatory properties

Unique electronic and optical properties

Can be utilized in the development of functional materials for electronic and optoelectronic devices

Upstream product

• 188290-36-0 thiophene 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 1003-09-4 2-bromothiophene 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 578-57-4 2-bromoanisole 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 96-43-5 2-thienyl chloride 
• 190788-60-4 pinacol 2-anisylboronate 
• 766-51-8 2-Chloroanisole 
• 45438-80-0 2-thienylzinc bromide 
• 100-66-3 methoxybenzene 
• 1026668-29-0 bis(2-thiophenyl)iodonium tosylate 
• 6165-68-0 thiophene boronic acid 
• 1504-74-1 2-methoxycinnamaldehyde 

Downstream Products

• 106584-13-8 2-(2'-hydroxyphenyl)thiophene 

Relevant academic research and scientific papers

METHOD FOR SYNTHESIZING BORONATE ESTER COMPOUND, SODIUM SALT OF BORONATE ESTER COMPOUND, AND METHOD FOR SYNTHESIZING THE SAME

An object is to establish a technology with which a boronate ester compound can be easily and efficiently synthesized at a low cost with a small number of steps without the need for a complex chemical method and reagents that need to be carefully handled. A further object is to establish a sodium salt of a boronate ester compound that is a novel compound and a technology for synthesizing the sodium salt of a boronate ester compound. Provided are a sodium salt of a boronate ester compound and a method for synthesizing a boronate ester compound or a sodium salt of a boronate ester compound that includes reacting, in a reaction solvent, an organic chloride with a dispersion product obtained by dispersing sodium in a dispersion solvent to obtain an organic sodium compound, and reacting the obtained organic sodium compound with a borate ester compound to obtain a boronate ester compound or a sodium salt of a boronate ester compound.

BIARYL PHENOXY GROUP IV TRANSITION METAL CATALYSTS FOR OLEFIN POLYMERIZATION

Embodiments are directed to catalyst systems comprising at least one metal ligand complex and to processes for polyolefin polymerization incorporating the catalyst systems. The metal ligand complexes have the following structures:

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.

Iodide-mediated or iodide-catalyzed demethylation and friedel-crafts C-H borylative cyclization leading to thiophene-fused 1,2-oxaborine derivatives

The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2′-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure.

Iodine-Catalyzed Synthesis of Chalcogenophenes by the Reaction of 1,3-Dienyl Bromides and Potassium Selenocyanate/Potassium Sulfide (KSeCN/K2S)

The methods available for the synthesis of chalcogenophenes, in general, are associated with drawbacks of harsh conditions, use of costly metals, broad applicability, tedious purification process and low yield. To avoid these drawbacks a transition metal-free iodine-catalyzed reaction of aryl-susbstituted 1,3-dienyl bromides with potassium selenocyanate/potassium sulfide (KSeCN/K2S) leading to the corresponding selenophenes and thiophenes has been developed. Iodine is relatively benign, less expensive and readily available. Several diversely substituted selenophenes and thiophenes have been obtained by this procedure in high yields. Using this procedure 2-(4-chlorophenyl)thiophene, a key intermediate for the synthesis of a melanin concentrating hormone receptor ligand involved in the treatment of eating disorders, weight gain, obesity, depression and anxiety has been synthesized. Although the reaction is one-pot essentially it proceeds in two steps involving a selenocyanate/thiolate intermediate leading to the selenophene/thiophene. The simple operation, use of inexpensive reagents and a metal-free process make this procedure more attractive for an easy access to substituted selenophenes and thiophenes. (Figure presented.).

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.

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.

General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand

A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.

General and highly efficient fluorinated-N-heterocyclic carbene-based catalysts for the palladium-catalyzed Suzuki-Miyaura reaction

A general and highly efficient trifluoromethylated-N-heterocyclic carbene (NHC)-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction was reported. In the presence of the catalyst, reactions of non-activated aryl chlorides and triflates with aryl boronic acids occurred at room temperature with good to excellent yields (63-98%). In addition, catalysts generated from a combination of Pd(OAc)2/imidazolium salt 6a is not only effective for the coupling of heteroaryl boronic acid with aryl halides and heteroaryl halides, but also efficient for coupling of other heteroaryl halides and heteroaryl boronic acids. Finally, the catalyst is highly effective for Suzuki-Miyaura reaction of aryl bromides and chlorides with 0.01-0.1 mol % loading if the temperature was raised at refluxed THF/H2O.

A mild negishi cross-coupling of 2-heterocyclic organozinc reagents and aryl chlorides

A mild Negishi cross-coupling of 2-heterocyclic organozinc reagents and aryl chlorides is described. The use of Pd2(dba)3 and X-Phos as a ligand provides high yields for many examples. An efficient method to generate the organozinc reagents at room temperature is also demonstrated.