26510-95-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a synthetic intermediate for the production of 2-(carboethoxy)-3-(4′-bromo)phenylquinoxaline 1,4-dioxide, which has potential applications in the development of pharmaceuticals, particularly those targeting specific biological pathways or receptors.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER serves as a valuable building block for the synthesis of a wide range of organic compounds, including those with potential applications in various industries such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is also utilized in research and development settings to explore its reactivity, properties, and potential applications in the creation of new molecules and materials with specific functions or improved performance.

InChI:InChI=1/C11H11BrO3/c1-2-15-11(14)7-10(13)8-3-5-9(12)6-4-8/h3-6H,2,7H2,1H3

Upstream product

• 99-90-1 para-bromoacetophenone 
• 105-58-8 Diethyl carbonate 
• 623-73-4 diazoacetic acid ethyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 141-97-9 ethyl acetoacetate 
• 313225-01-3 (1H-benzo[d][1,2,3]triazol-1-yl)(4-bromophenyl)methanone 
• 70-11-1 α-bromoacetophenone 
• 141-78-6 ethyl acetate 
• 586-75-4 4-chlorobenzoyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 586-76-5 4-Bromobenzoic acid 
• 6148-64-7 ethyl potassium malonate 

Downstream Products

• 100116-20-9 3-(4-bromo-phenyl)-3-thiosemicarbazono-propionic acid ethyl ester 
• 914222-57-4 2-(4-bromo-phenyl)-quinolin-4-ol 
• 5010-37-7 2-(4-bromo-phenyl)-5-hydroxy-benzofuran-3-carboxylic acid ethyl ester 
• 124202-13-7 2,6-bis-(4-bromo-phenyl)-benzo[1,2-b;4,5-b']difuran-3,7-dicarboxylic acid diethyl ester 
• 367928-57-2 5-(4-bromo-phenyl)-1,2-dihydro-pyrazol-3-one 
• 63131-18-0 C₁₅H₂₀BrO₄PS 
• 63131-19-1 C₁₆H₂₂BrO₄PS₂ 
• 63131-17-9 C₁₆H₂₂BrO₃PS₂ 
• 81729-04-6 ethyl α-p-bromobenzoylcinnamate 
• 116404-03-6 Diethyl 2,4-di(p-bromobenzoyl)-3-(p-methoxyphenyl)pentanedioate 
• 116342-20-2 5-(p-bromophenyl)-5-hydroxy-3-methyl-2,4-diethoxycarbonylcyclohexanone 
• 96723-02-3 5-(4-Bromo-phenyl)-1-(3-chloro-phenyl)-1H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 96723-01-2 5-(4-Bromo-phenyl)-1-m-tolyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 98815-53-3 C₁₁H₉⁽²⁾H₂BrO₃ 

Relevant academic research and scientific papers

Synthesis of 4-cyano pyrroles via mild Knorr reactions with β-ketonitriles

Mild methods for conducting Knorr chemistry with β-ketonitriles were developed. This enabled the preparation of 4-cyanopenta-substituted pyrroles and gave access to α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor potentiators for biol

Organic photovoltaics of diketopyrrolopyrrole copolymers with unsymmetric and regiorandom configuration of the side units

Diketopyrrolopyrrole (DPP) is a representative electron acceptor incorporated into narrow-bandgap polymers for organic photovoltaic cells (OPV). Commonly, identical aromatic units are attached to the sides of the DPP unit, forming symmetric DPP polymers. Herein we report the synthesis and characterization of DPP copolymers consisting of unsymmetric configurations of the side aromatics. The unsymmetric DPP copolymer with thienothiophene and benzene side moieties exhibits good solubility owing to the twisted dihedral angle at benzene and regiorandom configuration. A significant shallowing of the highest occupied molecular orbital level is observed in accordance with the electron-donating nature of the side units (benzene, thiophene, and thienothiophene). The overall power conversion efficiencies of the unsymmetric DPPs (2.3-2.4%) are greater than that of the centrosymmetric analogue (0.45%), which is discussed in view of bulk heterojunction morphology, polymer crystallinity, and space-charge-limited current mobilities. This comparative study highlights the effect of unsymmetric design on the molecular stacking and OPV performance of DPP copolymers.

Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines

A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.

Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones

A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β’-Keto-β-Amino Esters via Dynamic Kinetic Resolution

An iridium/f-diaphos catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti β’-hydroxy-β-amino esters were obtained in moderate to good yields (60–95%) with 72–99% ees and 91:9 to 99:1 drs. This protocol tolerates various functional groups and could be easily conducted on gram scale with lower catalyst loading (TON up to 9100). (Figure presented.).

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Promising new inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 4- arylcoumarin and monoterpenoid moieties as components of complex antitumor therapy

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is an important DNA repair enzyme in humans, and a current and promising inhibition target for the development of new chemosensitizing agents due to its ability to remove DNA damage caused by topoisomerase 1 (Top1) poisons such as topotecan and irinotecan. Herein, we report our work on the synthesis and characterization of new Tdp1 inhibitors that combine the arylcoumarin (neoflavonoid) and monoterpenoid moieties. Our results showed that they are potent Tdp1 inhibitors with IC50 values in the submicromolar range. In vivo experiments with mice revealed that compound 3ba (IC50 0.62 μM) induced a significant increase in the antitumor effect of topotecan on the Krebs-2 ascites tumor model. Our results further strengthen the argument that Tdp1 is a druggable target with the potential to be developed into a clinically-potent adjunct therapy in conjunction with Top1 poisons.

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

An efficient route for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives promoted by CBr4 in one pot

A metal-free one-pot method for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives was proposed mediated by CBr4. The reaction went through ring formation and opening processes with only two protons leaving and the thermodynamically favorable products were selectively formed in moderate to good yields.