7287-40-3

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 5-hydroxy-2-methyl-3-benzofurancarboxylate is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique molecular structure, which includes a benzofuran core and additional functional groups, makes it a versatile building block in the development of new therapeutic agents.
Used in Chemical Research:
Ethyl 5-hydroxy-2-methyl-3-benzofurancarboxylate is used as a research compound in the field of organic chemistry. Its reactivity and the presence of various functional groups make it an interesting subject for studying reaction mechanisms, synthesis strategies, and the exploration of new chemical properties.
Used in Flavor and Fragrance Industry:
Ethyl 5-hydroxy-2-methyl-3-benzofurancarboxylate is used as a flavoring agent or a fragrance ingredient in the food and cosmetics industries. Its aromatic properties and the ability to mimic natural scents make it a valuable component in creating complex and appealing sensory experiences.
Used in Material Science:
Ethyl 5-hydroxy-2-methyl-3-benzofurancarboxylate is used as a component in the development of new materials with specific properties. Its molecular structure can be incorporated into polymers or other materials to impart unique characteristics, such as improved stability, enhanced reactivity, or tailored physical properties.

InChI:InChI=1/C12H12O4/c1-3-15-12(14)11-7(2)16-10-5-4-8(13)6-9(10)11/h4-6,13H,3H2,1-2H3

Upstream product

• 123-31-9 hydroquinone 
• 141-97-9 ethyl acetoacetate 
• 106-51-4 p-benzoquinone 
• 21759-71-7 ethyl N-methyl-β-aminocrotonate 
• 75785-33-0 α-(Hydrochinonyl)-β-(methylamino)-crotonsaeureethylester 

Downstream Products

• 7287-51-6 ethyl 5-methoxy-2-methylbenzofuran-3-carboxylate 
• 82039-84-7 5-hydroxy-2-methyl-1-benzofuran-3-carboxylic acid 
• 1313849-17-0 C₂₄H₁₅BrN₂O₇S 
• 1313833-06-5 C₂₅H₁₈BrNO₆S 
• 1313858-22-8 C₂₅H₁₆BrNO₇S 
• 1600533-99-0 ethyl 2-methyl-5-phenoxybenzofuran-3-carboxylate 
• 1600534-00-6 ethyl 2-methyl-5-(o-tolyloxy)benzofuran-3-carboxylate 
• 1600534-01-7 ethyl 2-methyl-5-(p-tolyloxy)benzofuran-3-carboxylate 
• 1600534-02-8 ethyl 5-(4-methoxyphenoxy)-2-methylbenzofuran-3-carboxylate 
• 1966107-70-9 C₂₄H₂₅F₃N₂O₃ 
• 29735-88-4 5-methoxy-2-methylbenzofuran-3-carboxylic acid 
• 13391-27-0 5-methoxy-2-methylbenzofuran 

Relevant academic research and scientific papers

Synthesis method 4 -cycloheximide methyl substituted benzofuran derivative

The invention provides a synthesis method of 4 - cycloheximide methyl substituted benzofuran derivatives. Belong to organic synthesis technical field. After the Lewis-methyl benzofuran 5 - carboxylic acid is obtained -2 -methoxy -3 -methylbenzofuran 5 - carboxylic acid and then subjected to a hydrolysis reaction under basic conditions to obtain -2 -methoxy -3 -methylbenzofuran 5 - carboxylic acid, and then reacted with -2 - aniline in the presence of a condensing agent and a base to obtain -3 -methoxy R - methyl 5 -2 - R -phenyl benzofuran -3 - N formamide. After demethyl reaction 5 - hydroxyl -2 - methyl - N-R -phenyl benzofuran -3 - formamide was obtained, and finally, formaldehyde was added. Of the cycloheximide Mannich resulted in the final product.

Structural insight into the optimization of ethyl 5-hydroxybenzo[g]indol-3-carboxylates and their bioisosteric analogues as 5-LO/m-PGES-1 dual inhibitors able to suppress inflammation

The release of pro-inflammatory mediators, such as prostaglandines (PGs) and leukotrienes (LTs), arising from the arachidonic acid (AA) cascade, play a crucial role in initiating, maintaining, and regulating inflammatory processes. New dual inhibitors of 5-lipoxygenase (5-LO) and microsomal prostaglandin E2 synthase-1 (mPGES-1), that block, at the same time, the formation of PGE2 and LTs, are currently emerged as a highly interesting drug candidates for better pharmacotherapie of inflammation-related disorders. Following our previous studies, we here performed a detailed structure-based design of benzo[g]indol-3-carboxylate derivatives, disclosing several new key factors that affect both enzyme activity. Ethyl 2-(3,4-dichlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (4b, RAF-01) and ethyl 2-(3,4-dichlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (7h, RAF-02) emerged as the most active compounds of the series. Additionally, together with selected structure based analogues, both derivatives displayed significant in vivo anti-inflammatory properties. In conclusion, modeling and experimental studies lead to the discovery of new candidate compounds prone to further developments as multi-target inhibitors of the inflammatory pathway.

Highly efficient benzodifuran based ruthenium sensitizers for thin-film dye-sensitized solar cells

The synthesis of 4,4′-dibenzodifuran-2,2′-bipyridine derivatives as ligands of organic ruthenium dyes for DSSC applications is described. Two new heteroleptic ruthenium complexes have been prepared and compared with commercially available N719 and Z907 dyes, using dip dyeing and flow dyeing methods in large area testing cells prepared for industrial purposes. The newly synthesized dyes revealed higher solar-to-electric energy conversion efficiency (η), measured at the AM1.5G conditions, up to 21% compared to N719 and up to 46% compared to Z907, and external quantum efficiency of 53%. These results can be explained by enhanced light-harvesting of the benzodifuran moiety of the dyes that is related to photocurrent.

Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs

Several new benzofuran derivatives were synthesized, via appropriate synthetic route as anti-inflammatory agents. The anti-inflammatory activity of the prepared compounds was evaluated using carrageenan rat model. Among the synthesized compounds, some compounds showed comparable anti-inflammatory activity to nimesulide, the standard drug taken for anti-inflammatory studies. Docking study of the prepared compounds was performed for the study of interaction of molecules with the active site of COX-2. Preliminary biological studies and docking gave an interesting insight, into the validity of employing benzofuran analogues as good anti-inflammatory agent.

Synthesis, discovery and preliminary SAR study of benzofuran derivatives as angiogenesis inhibitors

A series of benzofuran derivatives were synthesized and evaluated against HUVEC proliferation. Among these compounds, compound 32 exhibited good inhibitory activity and remarkable selectivity to HUVEC. Our current data suggested that array order of methyl, acrylate and carboxylate groups in benzofuran scaffold is the basic requirement for inhibitory activity against HUVEC proliferation. These results demonstrated that benzofuran scaffold represents a promising structural core to discover a new class of active and selective angiogenesis inhibitors.

Lewis acid catalyzed Nenitzescu indole synthesis

A novel method for Lewis acid catalyzed Nenitzescu indole syntheses of 5-hydroxyindoles bearing different substituents in positions 1 (Alk, Bn, Ar), 2 (Me, Et, Ph), and 3 (COOEt, COMe, CONHPh) as well as tricyclic derivatives are reported. The method is simple, rapid, efficient, and allows preparation of hydroxyindoles from 1,4-benzoquinone and enamines in good to excellent yields with the use of low-polar solvents in the presence of weak Lewis acids catalysts. The formation of 5-hydroxyindoles under such mild conditions is explained in terms of a non-redox mechanism.