1717-42-6

Basic information

• Product Name: 3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER
• Synonyms: ETHYL (3-TRIFLUOROMETHYLBENZOYL)ACETATE;ETHYL 3-(3-TRIFLUOROMETHYL-PHENYL)-3-OXOPROPANOATE;3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER;3-(3-Trifluoromethylphenyl)-3-oxo-propionic acid ethyl ester;Ethyl 2-(3-trifluoromethylbenzoyl)acetate;Ethyl (3-trifluoroMethylbenzoyl)acetate
• CAS NO: 1717-42-6
• Molecular Formula: C₁₂H₁₁F₃O₃
• Molecular Weight: 260.21
• Product Categories: C12 to C63;Carbonyl Compounds;Esters;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 1717-42-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 250-251 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.267 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00399mmHg at 25°C
• Refractive Index: n20/D 1.4850(lit.)
• CAS DataBase Reference: 3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER(1717-42-6)
• EPA Substance Registry System: 3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER(1717-42-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1717-42-6(Hazardous Substances Data)

Usage

Description

3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER is an organic compound with a complex chemical structure, characterized by its ester functional group and a trifluoromethylphenyl moiety. It is a versatile intermediate in the synthesis of various pharmaceuticals and chemical compounds due to its unique reactivity and structural features.

Uses

Used in Pharmaceutical Industry:
3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER is used as a reactant for the preparation of pyrido[1,2-a]benzimidazoles, which are known for their cytotoxic and antiplasmodial properties. These compounds are valuable in the development of new drugs to treat cancer and malaria.
Used in Chemical Synthesis:
3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER is used as a reactant for the preparation of diaryl-substituted pyrazoles, which are potent CCR2 receptor antagonists. These antagonists have potential applications in the treatment of various inflammatory and autoimmune diseases.
Used in Organic Chemistry:
3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER is utilized in acid-catalyzed addition/annulation reactions, which are important for the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Heterocyclic Chemistry:
3-OXO-3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID ETHYL ESTER is used in cyclocondensation reactions with diaminophenylpyrazole, leading to the formation of novel heterocyclic compounds with potential applications in various fields, including pharmaceuticals and materials science.

InChI:InChI=1/C11H9F3O3/c1-2-17-10(16)9(15)7-4-3-5-8(6-7)11(12,13)14/h3-6H,2H2,1H3

Upstream product

• 105-58-8 Diethyl carbonate 
• 76783-59-0 ethyl 3-(trifluoromethyl)benzoate 
• 141-78-6 ethyl acetate 
• 442157-13-3 2-diazo-3-hydroxy-3-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 6148-64-7 ethyl potassium malonate 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 349-76-8 3'-(trifluoromethyl)acetophenone 
• 58686-69-4 ethyl 3-(3-(trifluoromethyl)phenyl)propiolate 
• 454-92-2 3-(trifluoromethyl)benzoic acid 

Downstream Products

• 1534-42-5 2-phenyl-5-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyrazol-3-one 
• 32577-69-8 3-(3-(trifluoromethyl)phenyl)isoxazol-5(4H)-one 
• 98305-67-0 2-Amino-6-(3-trifluoromethyl-phenyl)-3H-pyrimidin-4-one 
• 936947-29-4 2-naphthalen-2-yl-5-(3-trifluoromethyl-phenyl)-2,4-dihydro-pyrazol-3-one 
• 66129-59-7 2-(3-trifluoromethylbenzoyl)-3-dimethylamino-acrylic acid ethyl ester 
• 936947-79-4 5-bromo-1-naphthalen-2-yl-3-(3-trifluoromethyl-phenyl)-1H-pyrazole 
• 936948-61-7 4-[2-naphthalen-2-yl-5-(3-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-but-3-yn-1-ol 
• 936946-18-8 4-[2-naphthalen-2-yl-5-(3-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-butan-1-ol 
• 936949-33-6 4-[2-naphthalen-2-yl-5-(3-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-butyric acid 
• 635324-58-2 ethyl 4-chloro-1-methyl-6-(3-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 635324-88-8 6-methyl-4-(3-trifluoromethyl-phenyl)-1,6-dihydro-2H-1,2,5,6,7-pentaaza-as-indacen-3-one 
• 635325-70-1 4-hydroxy-1-methyl-6-(3-trifluoromethyl-phenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 635324-67-3 ethyl 4-chloro-6-[3-(trifluoromethyl)phenyl]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 635325-79-0 4-hydroxy-1-phenyl-6-(3-trifluoromethyl-phenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 

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.

Efficient Synthesis of Functionalized β-Keto Esters and β-Diketones through Regioselective Hydration of Alkynyl Esters and Alkynyl Ketones by Use of a Cationic NHC–AuICatalyst

Regioselective hydration of α-alkynyl esters and ketones by using a cationic NHC–AuIcatalyst results in β-keto esters and β-diketones, respectively. Controlled release of water in acetone by aldol self-condensation under the reaction conditions makes acetone as better solvent than 1,4-dioxane/water for the hydration of α-alkynyl esters having sensitive ester moieties.

Access to β-keto esters by palladium-catalyzed carbonylative coupling of aryl halides with monoester potassium malonates

New tricks for an old dog: The Pd-catalyzed carbonylative α-arylation of monoethyl potassium malonates with aryl bromides and reactive aryl chlorides provides a simple and direct route to aryl β-ketoesters. Because only stoichiometric amounts of carbon monoxide are employed, the method is ideal for the introduction of carbon isotopes into more complex structures. Copyright