718-08-1

Basic information

• Product Name: 3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER
• Synonyms: 3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER;3-keto-4-phenyl-butyric acid ethyl ester;ethyl 3-oxo-4-phenylbutanoate;ethyl 3-oxo-4-phenyl-butanoate;4-Phenyl-3-oxobutanoic acid ethyl ester;Ethyl 4-phenylacetoacetate;Benzenebutanoic acid, b-oxo-, ethyl ester;b-Oxo-benzenebutanoic acid ethyl ester
• CAS NO: 718-08-1
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24
• Mol File: 718-08-1.mol

Chemical Properties

• Boiling Point: 290℃
• Flash Point: 124℃
• Appearance: /
• Density: 1.091
• Vapor Pressure: 0.00209mmHg at 25°C
• Refractive Index: 1.054-1.059
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
• PKA: 10.49±0.46(Predicted)
• CAS DataBase Reference: 3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER(718-08-1)
• EPA Substance Registry System: 3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER(718-08-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 718-08-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER is used as a synthetic intermediate for the preparation of pyrazolone derivatives, which are known for their antiprion properties. These compounds have the potential to inhibit the formation of prion proteins, which are associated with neurodegenerative diseases such as Creutzfeldt-Jakob disease and bovine spongiform encephalopathy (BSE), commonly known as mad cow disease.
Used in Biochemical Research:
In the field of biochemical research, 3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER is used as a precursor for the synthesis of pyrrolinylaminopyrimidine analogs. These analogs act as inhibitors of AP-1 and NF-κB mediated gene expression, which are crucial for regulating various cellular processes, including inflammation, immune response, and cell proliferation. By inhibiting these pathways, pyrrolinylaminopyrimidine analogs can potentially be used to develop treatments for various diseases and conditions, such as cancer and inflammatory disorders.
Used in Chemical Synthesis:
3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER is also utilized in the chemical synthesis industry as a versatile building block for the creation of various organic compounds. Its reactivity and functional groups make it suitable for use in a wide range of chemical reactions, allowing for the development of new and innovative products.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 78, 2001 DOI: 10.1021/jm001034kChemical and Pharmaceutical Bulletin, 30, p. 2440, 1982 DOI: 10.1248/cpb.30.2440

Synthesis

The synthesis of Ethyl 3-oxo-4-phenylbutanoate is as follows:Monoethyl monopotassium malonate (12.9 g, 2.3 equivalents) was mixed with tetrahydrofuran (200 ml), and the mixture was cooled to 5°C. Triethylamine (8.2 g, 2.5 equivalents) and magnesium chloride (8.62 g, 2.8 equivalents) were added, and the mixture was stirred at 5 to 20°C for 3 hours. The reaction mixture was cooled to 5°C. Phenacyl chloride (5 g, 32 mmol, 1 equivalent) was gradually added, and the mixture was stirred at 5 to 20°C for 63 hours. The mixture was cooled to 5°C, and 1 N hydrochloric acid (30 ml) was added. Tetrahydrofuran was evaporated away under reduced pressure, and extraction was carried out with ethyl acetate (50 ml). The organic layer was washed with 1 N hydrochloric acid (30 ml), water (10 ml), saturated aqueous solution of sodium hydrogencarbonate (30 ml) and water (10 ml) in order. The solvent was evaporated away under reduced pressure to obtain the Ethyl 3-oxo-4-phenylbutanoate as a pale yellow oil (5.82 g, yield: 86 %).

InChI:InChI=1/C12H14O3/c1-2-15-12(14)9-11(13)8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

Upstream product

• 412019-21-7 ethyl 2-acetyl-3-oxo-4-phenylbutanoate 
• 32864-38-3 tert-Butyl ethyl malonate 
• 103-80-0 phenylacetyl chloride 
• 1071-46-1 hydrogen ethyl malonate 
• 64-17-5 ethanol 
• 66696-84-2 5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 140-29-4 phenylacetonitrile 
• 105-36-2 ethyl bromoacetate 
• 95092-10-7 N-methoxy-N-methyl-2-phenylacetamide 
• 141-78-6 ethyl acetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 122-78-1 phenylacetaldehyde 
• 60-29-7 diethyl ether 
• 7664-41-7 ammonia 

Downstream Products

• 855161-56-7 4-benzyl-5-hydroxy-7-methyl-coumarin 
• 176519-53-2 ethyl 2-isopropyl-3-oxo-4-phenylbutanoate 
• 102473-93-8 2,4-dioxo-3,6-diphenyl-cyclohexanecarboxylic acid ethyl ester 
• 855161-63-6 4-benzyl-5,7-dihydroxy-coumarin 
• 102657-43-2 6-(3,4-dimethoxy-phenyl)-2,4-dioxo-3-phenyl-cyclohexanecarboxylic acid ethyl ester 
• 75523-28-3 5-benzyl-1,2-dihydropyrazol-3-one 
• 132-86-5 1,3-dihydroxynaphthalene 
• 135608-75-2 benzyl carbamate 
• 58190-83-3 2-phenylacetyl-hexanoic acid ethyl ester 
• 76595-36-3 ethyl 2-acetoxy-3-oxo-4-phenylbutanoate 
• 412323-19-4 2-(4-nitro-benzyl)-4-phenyl-acetoacetic acid ethyl ester 
• 916248-70-9 diethyl (phenylacetyl)succinate 
• 861067-78-9 2-phenethyl-4-phenyl-acetoacetic acid ethyl ester 
• 856118-83-7 ethyl 2-benzyl-4-phenyl-1H-pyrrole-3-carboxylate 

Relevant articles and documents

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NRF 2 ACTIVATOR

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