146137-92-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester is used as a chemical intermediate for the synthesis of pharmaceutical compounds. Its unique structure, including the trifluoromethyl group, may contribute to the development of new drugs with improved pharmacological properties, such as enhanced potency, selectivity, or bioavailability.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester is utilized as a building block for the creation of novel agrochemicals. Its specific structural features could be leveraged to design pesticides or herbicides with increased effectiveness, selectivity, and reduced environmental impact.
Further Research and Development:
Due to the potential applications of 5-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester in both pharmaceutical and agrochemical industries, ongoing research and development are essential. This includes exploring its chemical reactivity, evaluating its biological activity, and assessing its safety and efficacy in various applications. The ultimate goal is to harness the unique properties of 5-TRIFLUOROMETHYL-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER to create innovative products that can address current challenges in healthcare and agriculture.

InChI:InChI=1/C11H7F3O2S/c1-16-10(15)9-5-6-4-7(11(12,13)14)2-3-8(6)17-9/h2-5H,1H3

Upstream product

• 2365-48-2 Methyl thioglycolate 
• 146137-78-2 2-fluoro-5-trifluoromethylbenzaldehyde 
• 922-67-8 propynoic acid methyl ester 
• 207974-07-0 2-(methylthio)-5-(trifluoromethyl)aniline 
• 402-44-8 4-Fluorobenzotrifluoride 

Downstream Products

• 244126-64-5 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid 

Relevant academic research and scientific papers

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

Enantioselective Synthesis of Five-Membered-Ring Atropisomers with a Chiral Rh(III) Complex

Axially chiral atropisomeric compounds are widely applied in asymmetric catalysis and medicinal chemistry, and efficient methods for their synthesis are in high demand. This applies in particular to atropisomers derived from five-membered aromatic rings because their lower barrier for rotation among the biaryl axis limits their asymmetric synthesis. We report here an enantioselective C-H functionalization method using our chiral RhJasCp complex for the synthesis of the biaryl atropisomer types that can be accessed from three different five-membered-ring heterocycles.

Preparation of Benzothiophenes and Benzoselenophenes from Arylamines and Alkynes via Radical Cascade Reactions

An intermolecular radical cascade reaction between readily prepared o-methylthio-arylamines or o-methylselanyl-arylamines and alkynes for the preparation of valuable benzothiophenes or benzoselenophenes is reported. These transformations occur efficiently with complete regioselectivity and the products are obtained in moderate to good yields. The current protocol is successfully applied to the synthesis of the key intermediates of the drug raloxifene and an AT1receptor antagonist.

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R1and R2) at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog 7f as a highly potent UT antagonist with an IC50value of 25?nM. Despite having a good metabolic stability, 7f is a potent inhibitor of CYP isozyme and displays an unsuitable PK profile.

AGRICHEMICAL COMPOSITION AND METHOD OF PROMOTING GROWTH OF PLANT

An agrichemical composition comprising a compound represented by the formula (1) and at least one insecticidally active compound selected from Group (A): Group (A): imidacloprid, clothianidin, thiamethoxam, acetamiprid, thiacloprid, nitenpyram, sulfoxaflor, flupyradifurone, imidaclothiz, cycloxaprid, abamectin, emamectin, emamectin benzoate, milbemectin, doramectin, lepimectin, flubendiamide, chlorantraniliprole, cyantraniliprole, fipronil, ethiprole, acetoprole, vaniliprole, pyriprole, pyrafluprole, thiodicarb, aldicarb, oxamyl, methiocarb, carbofuran, carbosulfan, fenitrothion, malathion, dimethoate and the like.

AGRICHEMICAL COMPOSITION AND METHOD OF PROMOTING GROWTH OF PLANT

An agrichemical composition comprising a compound represented by the formula (1) and at least one fungicidally active compound selected from Group (A). Group (A): metalaxyl, metalaxyl-M, benalaxyl, benalaxyl-M, pyraclostrobin, trifloxystrobin, azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim methyl, picoxystrobin, metconazole, ipconazole, tebuconazole, difenoconazole, epoxiconazole, fluquinconazole, triticonazole, triadimenol, prothioconazole, propioconazole, prochloraz, penconazole, flusilazole, diniconazole, bromuconazole, cyproconazole, triflumizole, tetraconazole, myclobutanil, bitertanol, imazalil and the like.

METHOD FOR PROMOTING PLANT GROWTH

Disclosed is a method for promoting the growth of a plant, comprising treating the plant with an effective amount of a compound represented by the following formula (1):, wherein any one of R1, R2, R3 and R4 represents a trifluoromethyl group, the others represent a hydrogen atom, and R5 represents a methyl group or an ethyl group.

METHOD FOR PROMOTING PLANT GROWTH

Disclosed is a method for promoting the growth of a plant, comprising treating the plant with an effective amount of a compound represented by the following formula (1):, wherein any one of R1, R2, R3 and R4 represents a trifluoromethyl group, and the others represent a hydrogen atom, or an agriculturally acceptable salt thereof.

Fluorine as an ortho-directing group in aromatic metalation: A two step preparation of substituted benzo[b] thiophene-2-carboxylates

A simple 2-step synthesis of B-ring substituted benzo[b]thiophene-2-carboxylates from aryl fluorides has been developed. The route involves a selective lithiation ortho to fluorine, followed by formylation, and subsequently, displacement of fluorine with