35338-15-9

Basic information

• Product Name: (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE
• Synonyms: (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE
• CAS NO: 35338-15-9
• Molecular Formula: C₁₂H₁₁BrO₃
• Molecular Weight: 283.12
• Mol File: 35338-15-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 362.5°C at 760 mmHg
• Flash Point: 173°C
• Appearance: /
• Density: 1.413g/cm³
• Vapor Pressure: 1.92E-05mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE(35338-15-9)
• EPA Substance Registry System: (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE(35338-15-9)

Safety Data

• Hazardous Substances Data: 35338-15-9(Hazardous Substances Data)

Usage

General Description

(E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE is a chemical compound with the molecular formula C12H11BrO3. It is a yellow to brown solid, and its molecular weight is 289.12 g/mol. (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE is an ester, with a but-2-enoate group and a 4-(4-bromophenyl)-4-oxo motif. It is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds. (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE may be harmful if swallowed or inhaled, and it should be handled and stored with appropriate safety precautions.

InChI:InChI=1/C12H11BrO3/c1-2-16-12(15)8-7-11(14)9-3-5-10(13)6-4-9/h3-8H,2H2,1H3/b8-7+

Upstream product

• 108-86-1 bromobenzene 
• 64-17-5 ethanol 
• 39644-80-9 β-(4-bromobenzoyl)acrylic acid 
• 35497-00-8 Triphenyl-β-keto-p-bromphenylphosphonium 
• 117937-01-6 4-(4-bromophenyl)-4-hydroxybut-2-ynoic acid ethyl ester 
• 924-44-7 glyoxylic acid ethyl ester 
• 2928-58-7 (2-oxo-2-p-bromophenylethyl)triphenylphosphonium bromide 
• 99-73-0 para-bromophenacyl bromide 
• 5195-29-9 4-bromophenylglyoxal 
• 1071-46-1 hydrogen ethyl malonate 
• 99-90-1 para-bromoacetophenone 
• 1777-57-7 p-bromobenzoylmethylenetriphenylphosphorane 
• 20972-38-7 (E)-4-(4-bromophenyl)-4-oxobut-2-enoic acid 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1107060-58-1 1-(4-bromobenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester 
• 1116119-11-9 C₂₀H₁₈BrNO₃ 
• 1116119-20-0 C₂₀H₁₇Br₂NO₃ 
• 1353682-55-9 ethyl 6-(4-bromophenyl)-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate 
• 50636-57-2 6-(4-bromophenyl)-3(2H)-pyridazin-3-one 
• 1353682-60-6 ethyl 5-(4-bromophenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-7-carboxylate 
• 1353682-57-1 ethyl 5-(4-bromophenyl)-2-(4-methylphenyl)-6,7-dihydropyrazolo[1,5-a]pyrimidine-7-carboxylate 

Relevant articles and documents

Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents

A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.

Base-Controlled Reactions through an Aldol Intermediate Formed between 2-Oxoaldehydes and Malonate Half Esters

A practical, atom-economical, base-directed, and highly efficient method for the generation of different selective products through a common aldol intermediate of 2-oxoaldehydes and malonate half esters is successfully developed. The addition of a strong basic environment (potassium tert-butoxide) catalyzed the synthesis of stable decarboxylative aldol products (α-hydroxy ketones), while the Doebner modification procedure resulted in decarboxylative elimination to (E)-α,β-unsaturated esters in good yields. The application of this method in one pot and one pot/two steps with azoles helped to develop regioselective α- and β-azolated products in appreciable yields.

Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives

Based on the appropriate choice of electrophiles, one-pot, multicomponent, enantioselective domino reactions have been realized which contain a five-step sequence and provide highly efficient access to potentially bioactive chroman-2-one derivatives as a single diastereoisomer with excellent enantioselectivities and in high yields. This new strategy could significantly improve the previous protocol by directly starting from commercial 2-hydroxybenzaldehydes rather than preformed lactols, which have to be synthesized in several additional steps. (Chemical Equation Presented).