33167-21-4

Basic information

• Product Name: 3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
• Synonyms: ETHYL 3-(3-CHLOROPHENYL)-3-OXOPROPANOATE;ETHYL (3-CHLOROBENZOYL)ACETATE;3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;Ethyl 2-(3-chlorobenzoyl)acetate;3-Chloro--oxobenzenepropanoic acid ethyl ester;Ethyl (3-chlorobenzoyl)acetate >=97%;3-(3-chlorophenyl)-3-keto-propionic acid ethyl ester;3-(3-chlorophenyl)-3-oxopropanoic acid ethyl ester
• CAS NO: 33167-21-4
• Molecular Formula: C₁₁H₁₁ClO₃
• Molecular Weight: 226.66
• Product Categories: C10 to C11;Carbonyl Compounds;Esters;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 33167-21-4.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 257-258 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.213 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000525mmHg at 25°C
• Refractive Index: n20/D 1.5460(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.91±0.46(Predicted)
• CAS DataBase Reference: 3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(33167-21-4)
• EPA Substance Registry System: 3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(33167-21-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 33167-21-4(Hazardous Substances Data)

Usage

Description

3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is an organic compound that serves as a versatile reagent and reactant in various chemical reactions and synthesis processes. It is characterized by its ability to participate in oxidative cross-coupling, chlorination, hydrosilylation, and other reactions, making it a valuable component in the fields of chemistry and pharmaceuticals.

Uses

Used in Chemical Synthesis:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reagent/reactant for oxidative cross-coupling via dioxygen activation with indoles. This application allows for the formation of new chemical bonds and the creation of complex molecular structures.
Used in Pharmaceutical Industry:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in the chlorination and hydrosilylation process for the synthesis of α-hydroxy β-amino acid derivatives. These derivatives are essential building blocks in the development of various pharmaceutical compounds.
Used in Chiral Lewis Base-Catalyzed Reduction:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER serves as a precursor for substrates in chiral Lewis base-catalyzed stereoselective reduction with trichlorosilane and water. This application is crucial for obtaining specific enantiomers, which are important in the pharmaceutical industry for their targeted therapeutic effects.
Used in Organic Synthesis:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in intramolecular cyclization reactions for the synthesis of dihydrofurans. These cyclic compounds are valuable intermediates in the synthesis of various organic molecules and natural products.
Used in Accelerating Reactions:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant to rate-accelerate Michael reactions, which are essential in the formation of carbon-carbon double bonds in various organic compounds.
Used in Oxidative Coupling:
3-(3-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in cerium ammonium nitrate-mediated oxidative coupling reactions. This application is vital for the formation of new carbon-carbon bonds and the synthesis of complex organic molecules.

InChI:InChI=1/C11H11ClO3/c1-2-15-11(14)7-10(13)8-4-3-5-9(12)6-8/h3-6H,2,7H2,1H3

Upstream product

• 618-46-2 m-Chlorobenzoyl chloride 
• 105-36-2 ethyl bromoacetate 
• 893643-63-5 2-(3-chloro-benzoyl)-3-oxo-butyric acid ethyl ester 
• 99-02-5 3'-Chloroacetophenone 
• 105-58-8 Diethyl carbonate 
• 6148-64-7 ethyl potassium malonate 
• 64-17-5 ethanol 
• 535-80-8 3-chlorobenzoate 
• 42428-03-5 (3-chlorophenyl)(1H-imidazol-1-yl)methanone 

Downstream Products

• 36309-40-7 6-(3-chlorophenyl)-2-thiouracil 
• 51725-85-0 3-(3-chlorophenyl)isoxazol-5(4H)-one 
• 76519-46-5 2-Amino-6-(3-chloro-phenyl)-3H-pyrimidin-4-one 
• 1026608-91-2 2-(3-Chloro-benzoyl)-pentanedioic acid diethyl ester 
• 194466-59-6 2-(3'-Chlorophenyl)-7-methyl-pyrido[1,2-a]pyrimidin-4-one 
• 194466-61-0 2-(3'-Chlorophenyl)-6,8-dimethyl-pyrido[1,2-a]pyrimidin-4-one 
• 784202-24-0 ethyl 3-chloro-α-[(dimethylamino)methylene]-β-oxobenzenepropanoate 
• 805231-20-3 [2-(3-chlorophenyl)-[1,3]dioxolan-2-yl]acetic acid ethyl ester 
• 1026889-57-5 3-(3-chlorobenzoyl)-6-hydroxymethyl-2-oxo-2H-1-benzopyran-2-one 
• 51699-45-7 (S)-(-)-1-(3'-Chlorophenyl)-1,3-Propanediol 
• 936947-00-1 5-(3-chloro-phenyl)-2-naphthalen-2-yl-2,4-dihydro-pyrazol-3-one 
• 936947-75-0 5-bromo-3-(3-chloro-phenyl)-1-naphthalen-2-yl-1H-pyrazole 
• 883989-35-3 (4S)-4-(3-chlorophenyl)-2-(4-nitrophenoxy)-1,3,2-dioxaphosphinane-2-oxide 
• 632327-18-5 (R)-(+)-1-(3-chlorophenyl)-1,3-propanediol 

Relevant articles and documents

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.

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.

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.