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
• Article Data: 65

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

Chemical Properties

Light-yellow Liquid.

Uses

Ethyl 3-oxo-4-phenylbutanoate is a useful synthetic intermediate. It is used to prepare pyrazolone derivatives as antiprion compounds. It is also used to prepare pyrrolinylaminopyrimidine analogs as inhibitors of AP-1 and NF-κB mediated gene expression.

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

• 32864-38-3 tert-Butyl ethyl malonate 
• 103-80-0 phenylacetyl chloride 
• 64-17-5 ethanol 
• 66696-84-2 5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 412019-21-7 ethyl 2-acetyl-3-oxo-4-phenylbutanoate 
• 60-29-7 diethyl ether 
• 7664-41-7 ammonia 
• 103-82-2 phenylacetic acid 
• 25832-09-1 3-oxo-4-phenyl-butyric acid 
• 6148-64-7 ethyl potassium malonate 
• 532-27-4 1-chloroacetophenone 
• 623-73-4 diazoacetic acid ethyl ester 
• 96-09-3 styrene oxide 
• 722-01-0 phenyl phenylacetate 

Downstream Products

• 855161-56-7 4-benzyl-5-hydroxy-7-methyl-coumarin 
• 861067-78-9 2-phenethyl-4-phenyl-acetoacetic acid ethyl ester 
• 101283-35-6 4-phenyl-acetoacetic acid anilide 
• 101729-50-4 3-anilino-4-phenyl-crotonic acid ethyl ester 
• 62282-32-0 benzyl 3-oxo-4-phenylbutanoate 
• 158779-36-3 3-N-allyl-6-phenylmethyl-2-thiouracil 
• 83633-44-7 diethyl 5-benzyl-3-methylpyrrole-2,4-dicarboxylate 
• 24090-86-6 3-Hydroxy-2-<(aethoxycarbonyl-phenyl-acetyl-methylen)-hydrazino>-naphthochinon-(1.4) 
• 103-79-7 1-phenyl-acetone 
• 223927-13-7 6-benzyl-2-butyl-3H-pyrimidin-4-one 
• 100142-46-9 6-benzyl-2-methylsulfanyl-3H-pyrimidin-4-one 
• 6336-50-1 6-benzyl-2-thiouracil 
• 20280-94-8 4-benzyl-7-hydroxycoumarin 
• 135608-75-2 benzyl carbamate 

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