26510-95-2

Basic information

• Product Name: 3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
• Synonyms: ETHYL 3-(4-BROMOPHENYL)-3-OXOPROPANOATE;ETHYL (4-BROMOBENZOYL)ACETATE;3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;3-(4-Bromophenyl)-3-oxo-propionic acid;Ethyl (4-bromobenzoyl)acetate,95%;ethyl3-(4-bromophenyl)-3-oxo-propionate;Benzenepropanoic acid,4-bromo-b-oxo-, ethyl ester;ethyle(4-bromobenzoyl)acetate
• CAS NO: 26510-95-2
• Molecular Formula: C₁₁H₁₁BrO₃
• Molecular Weight: 271.11
• Product Categories: C10 to C11;Carbonyl Compounds;Esters;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 26510-95-2.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 268-269 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 1.432 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000146mmHg at 25°C
• Refractive Index: n20/D 1.5700(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.56±0.25(Predicted)
• CAS DataBase Reference: 3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(26510-95-2)
• EPA Substance Registry System: 3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(26510-95-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 26510-95-2(Hazardous Substances Data)

Usage

Description

3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER, also known as Ethyl (4-bromobenzoyl)acetate, is a chemical compound derived from the synthesis involving ethyl acetylacetate, petroleum ether, NaOH, and 4-bromobenzoyl chloride. It is characterized by its clear yellow to light brown liquid appearance and is used as a key intermediate in the synthesis of various organic compounds.

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 
• 239094-36-1 ethyl-3-hydroxy-2-diazo-3-(4-bromophenyl)-propanoate 
• 70-11-1 α-bromoacetophenone 
• 623-53-0 ethyl methyl carbonate 
• 141-78-6 ethyl acetate 
• 586-75-4 4-chlorobenzoyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 105-36-2 ethyl bromoacetate 
• 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 articles and documents

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

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.

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.

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.