294881-08-6

Basic information

• Product Name: 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER
• Synonyms: 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER;2-BROMO-BETA-OXO-BENZENEPROPANOIC ACID METHYL ESTER;Methyl (2-bromobenzoyl)acetate;2-BroMo-b-oxo-benzenepropanoic acid Methyl ester
• CAS NO: 294881-08-6
• Molecular Formula: C₁₀H₉BrO₃
• Molecular Weight: 257.08
• Mol File: 294881-08-6.mol

Chemical Properties

• Boiling Point: 308.9±22.0 °C(Predicted)
• Appearance: /
• Density: 1.480±0.06 g/cm3(Predicted)
• PKA: 9.83±0.46(Predicted)
• CAS DataBase Reference: 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER(294881-08-6)
• EPA Substance Registry System: 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER(294881-08-6)

Safety Data

• Hazardous Substances Data: 294881-08-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER is used as a building block for the synthesis of various pharmaceuticals due to its unique chemical structure and reactivity, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER serves as an intermediate in the production of agrochemicals, aiding in the creation of compounds that can be used for pest control and crop protection.
Used in Fragrance and Flavor Industry:
3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER is utilized as a potential intermediate in the production of fragrances and flavors, where its chemical properties can be harnessed to create unique scents and tastes for various consumer products.
Used in Organic Synthesis:
As a versatile chemical intermediate, 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER is employed in organic synthesis for the preparation of a wide range of biologically active compounds, showcasing its importance in the synthesis of complex organic molecules.
Safety Precautions:
Given the potential toxicity and health hazards associated with 3-(2-BROMO-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER, it is crucial to exercise caution and implement proper safety measures when handling this chemical. This includes the use of appropriate personal protective equipment, working in well-ventilated areas, and adhering to established safety protocols to minimize exposure and ensure the well-being of individuals involved in its production and use.

Upstream product

• 79-20-9 acetic acid methyl ester 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 1323309-33-6 methyl 3-(2-bromophenyl)-3-hydroxypropanoate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 88-65-3 2-bromobenzoic-acid 
• 38330-80-2 monomethyl monopotassium malonate 
• 7154-66-7 2-bromobenzoic acid chloride 
• 2142-69-0 2-bromophenyl methyl ketone 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 1257230-35-5 1-benzyl 3-methyl 4-hydroxy-2-methylnaphthalene-1,3-dicarboxylate 
• 1257230-41-3 methyl 4-cyano-1-hydroxy-3-phenyl-2-naphthoate 
• 1257230-37-7 1-ethyl 3-methyl 4-hydroxy-2-phenylnaphthalene-1,3-dicarboxylate 
• 1269637-24-2 (E)-1-(2-(4-chlorostyryl)phenyl)ethan-1-one 
• 1323308-94-6 1-methylene-2-p-tolyl-1H-indene 
• 1323308-97-9 2-(4-chlorophenyl)-1-methylene-1H-indene 
• 1323308-98-0 1-methylene-2-(4-nitrophenyl)-1H-indene 
• 1323309-18-7 (E)-1-(2-(4-methylstyryl)phenyl)ethanone 
• 2142-69-0 2-bromophenyl methyl ketone 
• 1439356-84-9 methyl 1-methyl-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate 
• 1383740-54-2 methyl 2-(2-bromophenyl)-4,5-dicyanofuran-3-carboxylate 
• 1323309-33-6 methyl 3-(2-bromophenyl)-3-hydroxypropanoate 

Relevant articles and documents

Systematic asymmetric analog synthesis of fluspidine, a σ1 receptor ligand, to improve ligand affinity

Fluspidine is a high affinity ligand of the σ1 receptor. To further improve the ligand affinity, fluspidine analogs were systematically synthesized and screened herein. To design the modified ligand analogs, a docking simulation of the protein–ligand complex structure was examined. By using the developed synthetic strategy involving asymmetric catalytic 1,4-reduction of α,β -unsaturated carboxylic esters catalyzed by a chiral cobalt complex, 20 candidates of modified fluspidines were synthesized. The structure–activity relationships showed the development of a hybridized modified fluspidine. In addition, the inhibitory rate could be improved from 45% to 71%. This result demonstrates the importance of the development of a new synthetic method towards improving the ligand performance by providing a series of analogs.

Synthesis of fluspidine via asymmetric NaBH4 reduction of silicon enolates of β-keto esters

Asymmetric NaBH4 reduction catalyzed by the Co(II) complex of a chiral diamidine-type sp2N ligand, Naph-diPIM-dioxo-iPr, was successfully applied to 3-silyloxycinnamate substrates without over-reduction, giving quantitatively 3-silyloxy-3-arylpropionates with an enantiomer ratio of up to 99:1. The high utility was confirmed on a 30-g scale using 0.1 mol% catalyst. Both Z and E substrates could be converted to a single enantiomeric product by changing the ligand chirality. The relationship between the Z/E stereochemistry and the absolute configuration of the 1,4-reduction product provided important information about the mechanism underlying enantioface selection. Combination of the asymmetric catalysis with two other key steps, Suzuki coupling with an N-protected tetrahydropyridine boronic acid derivative and intramolecular bromo etherification, realized an efficient synthetic route to both enantiomers of fluspidine. The new strategy permits the introduction of substituents on the two aryl groups and piperidine ring, allowing for structural variations toward the development of higher performance σ1 receptor antagonists.

Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process

Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.

Trimethylchlorosilane-Mediated Mild α-Chlorination of 1,3-Dicarbonyl Compounds Promoted by Phenyliodonium Diacetate

Trimethylchlorosilane was used as chlorine source for the α-chlorination of 1,3-dicarbonyl compounds with phenyliodonium diacetate as oxidant at room temperature. The reaction allows the selective synthesis of α-monochlorinated products from different kinds of 1,3-dicarbonyl compounds in good yield. The potential possibility of this conversion for bromination has also been investigated.

Base initiated aromatization/CO bond formation: A new entry to O-pyrazole polyfluoroarylated ethers

A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the CO bond formation via the selective CF bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates.

Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives

A novel one-pot synthesis of the 2-substituted 3-carboxy-4-quinolone/ chromone derivatives from readily available 3-oxo-3-arylpropanoates and amides/acyl chlorides is reported, without any transition metal aid. The Royal Society of Chemistry 2013.

AuI-catalyzed intramolecular cyclization of 2-alkenylphenyl carbonyl compounds: Exploring the oxophilic Lewis acidity of AuI species

A AuI-catalyzed intramolecular cyclization reaction of 2-alkenylphenyl carbonyl compounds to afford a variety of indene, indenol, and indanone ring systems was developed. In this process, AuI serves to activate the carbonyl group of β-keto esters, aldehydes, and ketones, preferentially exhibiting oxophilicity in the presence of C-C multiple bonds. Furthermore, β-keto esters could participate as the electrophilic partner in reactions with carbon nucleophile such as alkenes. Copyright

Efficient synthesis of the structural core of tetracyclines by a palladium-catalyzed domino Tsuji-Trost-Heck-Mizoroki reaction

The Pd-catalyzed domino Tsuji-Trost-Heck-Mizoroki reactions of compounds 18, 27, and 34, respectively, each containing an allyl acetate and a halogen aryl moiety, lead to the formation of hexahydronaphthacenes 2 and 3 and octahy-droanthracene 4 in 62-81 % yield. The octahydroanthracene and hexahydronaphthacene motifs are found in many natural products, for example, the tetracycline antibiotics.