41607-95-8

Basic information

• Product Name: ETHYL (2-METHOXYBENZOYL)ACETATE
• Synonyms: ETHYL 3-(2-METHOXYPHENYL)-3-OXOPROPANOATE;ETHYL (2-METHOXYBENZOYL)ACETATE;3-(2-METHOXYPHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;2-Methoxybenzoylacetic acid ethyl ester;3-Oxo-3-(2-methoxyphenyl)propionic acid ethyl ester;β-Oxo-2-methoxybenzenepropionic acid ethyl ester;Ethyl (2-methyoxybenzoyl)acetate;Ethyl (2-Methoxybenzoyl)acetate 99%
• CAS NO: 41607-95-8
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24
• Product Categories: C12 to C63;Carbonyl Compounds;Esters
• Mol File: 41607-95-8.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 259-260 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.144 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000709mmHg at 25°C
• Refractive Index: n20/D 1.5320(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ETHYL (2-METHOXYBENZOYL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (2-METHOXYBENZOYL)ACETATE(41607-95-8)
• EPA Substance Registry System: ETHYL (2-METHOXYBENZOYL)ACETATE(41607-95-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 41607-95-8(Hazardous Substances Data)

Usage

Description

ETHYL (2-METHOXYBENZOYL)ACETATE is an organic compound that serves as a versatile intermediate in the synthesis of various chemical products. It is characterized by its ester functional group and aromatic ring structure, which contribute to its reactivity and utility in different chemical reactions.

Uses

Used in Pharmaceutical Industry:
ETHYL (2-METHOXYBENZOYL)ACETATE is used as a reactant for the preparation of potential herbicidal agents, contributing to the development of new and effective weed control solutions.
Used in Chemical Synthesis:
ETHYL (2-METHOXYBENZOYL)ACETATE is used as a reactant for the preparation of N-allyl/propargyl enamine carboxylates, which are important building blocks in the synthesis of various organic compounds.
Used in Enantioselective Catalysis:
ETHYL (2-METHOXYBENZOYL)ACETATE is used in enantioselective ruthenium-catalyzed hydrogenation reactions, where it plays a crucial role in the selective formation of chiral products with high enantiomeric purity.
Used in Hydrosilylation Reactions:
ETHYL (2-METHOXYBENZOYL)ACETATE is used in hydrosilylation reactions catalyzed by chiral BINAM N-heterocyclic carbene rhodium complex, facilitating the formation of new carbon-silicon bonds with high selectivity and efficiency.

InChI:InChI=1/C12H14O4/c1-3-16-12(14)8-10(13)9-6-4-5-7-11(9)15-2/h4-7H,3,8H2,1-2H3

Upstream product

• 606-45-1 2-methoxybenzoic acid methyl ester 
• 7335-26-4 ethyl 2-methoxybenzoate 
• 141-97-9 ethyl acetoacetate 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 141-78-6 ethyl acetate 
• 104600-18-2 2-(2-Methoxy-benzoyl)-malonic acid diethyl ester 
• 579-74-8 2-Methoxyacetophenone 
• 105-58-8 Diethyl carbonate 
• 623-73-4 diazoacetic acid ethyl ester 
• 135-02-4 ortho-anisaldehyde 
• 1071-46-1 hydrogen ethyl malonate 
• 105-53-3 diethyl malonate 
• 118-93-4 o-hydroxyacetophenone 
• 70200-18-9 ethyl 3-hydroxy-3-(2-methoxyphenyl)propionate 

Downstream Products

• 579-74-8 2-Methoxyacetophenone 
• 76103-94-1 3-(2-methoxy-phenyl)-3-oxo-propionic acid 
• 70311-27-2 2-methoxybenzenepropanoic acid ethyl ester 
• 190248-05-6 1,5-bis-(2-methoxy-phenyl)-pentane-1,5-dione 
• 118-93-4 o-hydroxyacetophenone 
• 55982-12-2 2-amino-6-(2-methoxy-phenyl)-3H-pyrimidin-4-one 
• 808759-94-6 3-(2-methoxy-phenyl)-3-oxo-propionic acid-(4-nitro-anilide) 
• 131517-02-7 3-(2-methoxy-phenyl)-3-oxo-propionic acid-(2-nitro-anilide) 
• 92963-33-2 3-(2-methoxy-phenyl)-3-oxo-propionic acid anilide 
• 939898-79-0 5-(2-methoxy-phenyl)-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 131517-03-8 3-(2-methoxy-phenyl)-3-oxo-propionic acid-(3-nitro-anilide) 
• 24050-67-7 5,7-dihydroxy-2'methoxyneoflavone 
• 119031-50-4 (Z)-3-Hydroxy-3-(2-methoxy-phenyl)-acrylic acid ethyl ester 
• 24031-70-7 3-(2-methoxyphenyl)isoxazol-5(4H)-one 

Relevant articles and documents

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.

Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against Mycobacterium tuberculosis

Inhibition of the mycolic acid pathway has proven a viable strategy in antitubercular drug discovery. The AccA3/AccD4/FadD32/Pks13 complex of Mycobacterium tuberculosis constitutes an essential biosynthetic mechanism for mycolic acids. Small molecules targeting the thioesterase domain of Pks13 have been reported, including a benzofuran-based compound whose X-ray cocrystal structure has been very recently solved. Its initial inactivity in a serum inhibition titration (SIT) assay led us to further probe other structurally related benzofurans with the aim to improve their potency and bioavailability. Herein, we report our preliminary structure-activity relationship studies around this scaffold, highlighting a natural product-inspired cyclization strategy to form coumestans that are shown to be active in SIT. Whole genome deep sequencing of the coumestan-resistant mutants confirmed a single nucleotide polymorphism in the pks13 gene responsible for the resistance phenotype, demonstrating the druggability of this target for the development of new antitubercular agents.

The synthesis and evaluation of triazolopyrimidines as anti-tubercular agents

We identified a di-substituted triazolopyrimidine with anti-tubercular activity against Mycobacterium tuberculosis. Three segments of the scaffold were examined rationally to establish a structure-activity relationship with the goal of improving potency and maintaining good physicochemical properties. A number of compounds displayed sub-micromolar activity against Mycobacterium tuberculosis with no cytotoxicity against eukaryotic cells. Non-substituted aromatic rings at C5 and a two-carbon chain connecting a terminal aromatic at C7 were preferred features; the presence of NH at C7 and a lack of substituent at C2 were essential for potency. We identified compounds with acceptable metabolic stability in rodent and human liver microsomes. Our findings suggest that the easily-synthesized triazolopyrimidines are a promising class of potent anti-tubercular agents and warrant further investigation in our search for new drugs to fight tuberculosis.