94-02-0

Basic information

• Product Name: Ethyl benzoylacetate
• Synonyms: AKOS 92622;AKOS BBS-00004233;3-OXO-3-PHENYLPROPIONIC ACID ETHYL ESTER;LABOTEST-BB LTBB001316;FEMA 2423;ETHYL BENZOYLACETATE;ETHYL BETA-KETO-BETA-PHENYLPROPIONATE;ETHYL 3-OXO-3-PHENYLPROPANOATE
• CAS NO: 94-02-0
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21
• EINECS: 202-295-3
• Product Categories: Pharmaceutical Intermediates;Pyridines
• Mol File: 94-02-0.mol
• Article Data: 185

Chemical Properties

• Melting Point: <0 °C
• Boiling Point: 265-270 °C(lit.)
• Flash Point: 147 °F
• Appearance: Brown/Powder
• Density: 1.11 g/mL at 25 °C(lit.)
• Vapor Density: 6.6 (vs air)
• Vapor Pressure: 0.00783mmHg at 25°C
• Refractive Index: n20/D 1.52(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: alcohol: miscible
• PKA: 9.85±0.23(Predicted)
• Water Solubility: INSOLUBLE
• Sensitive: Light Sensitive
• Merck: 14,3767
• BRN: 389944
• CAS DataBase Reference: Ethyl benzoylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl benzoylacetate(94-02-0)
• EPA Substance Registry System: Ethyl benzoylacetate(94-02-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: AF4878000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 94-02-0(Hazardous Substances Data)

Usage

Chemical Properties

Ethyl benzoylacetate has a brandy-like odor and sweet, woody, cherry, phenolic-like flavor.

Uses

Different sources of media describe the Uses of 94-02-0 differently. You can refer to the following data:
1. Ethyl benzoylacetate (Best) is used as intermediate for different organic synthesis. Product Data Sheet
2. Ethyl benzoylacetate (Best) is used as an intermediate for different organic synthesis Product Data Sheet
3. Ethyl benzoylacetate (Benzoylacetic acid ethyl ester) was used to prepare ethyl 2-fluoro-2-benzolyacetate. It was also used to synthesize iodonium ylides.

Preparation

By condensation of ethyl benzoate with ethyl acetate (via Claisen condensation) using sodium ethoxide; another method also known.

Taste threshold values

Taste characteristics at 10 ppm: sweet, cherry, fruity, berry-like with woody, jamy notes.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 1864, 1985 DOI: 10.1021/jm00150a018Journal of Heterocyclic Chemistry, 32, p. 723, 1995 DOI: 10.1002/jhet.5570320303The Journal of Organic Chemistry, 38, p. 2731, 1973 DOI: 10.1021/jo00955a040

General Description

Ethyl benzoylacetate is an ester. It undergoes microbial reduction by bakers′ yeast (Saccharomyces cerevisiae), Beauveria sulfurescens or Geotrichum candidum to afford ethyl (S)-3-hydroxy-3-phenylpropionate. It undergoes Claisen condensation reaction with malononitrile to afford 2-cyano-5-phenyl-3,5-dioxopentanonitrile which on cyclization followed by coupling with diazonium salts yields azo derivatives.

InChI:InChI=1/C11H12O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

Upstream product

• 10562-42-2 3,3-dichloro-1-phenyl-propenone 
• 569-37-9 ethyl 3-oxo-2-benzoylbutanoate 
• 64-19-7 acetic acid 
• 860764-26-7 2-benzoyl-3,3-bis-(4-dimethylamino-phenyl)-propionic acid ethyl ester 
• 93-89-0 benzoic acid ethyl ester 
• 4303-71-3 triphenylmethyl sodium 
• 141-78-6 ethyl acetate 
• 141-52-6 sodium ethanolate 
• 98-88-4 benzoyl chloride 
• 105-36-2 ethyl bromoacetate 
• 10364-94-0 1-benzoylimidazole 
• 6148-64-7 ethyl potassium malonate 
• 75-03-6 ethyl iodide 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 92653-70-8 2-(1-methyl-piperidin-4-yl)-5-phenyl-1,2-dihydro-pyrazol-3-one 
• 132856-90-7 1-methyl-2-(1-methyl-piperidin-4-yl)-5-phenyl-1,2-dihydro-pyrazol-3-one 
• 65658-66-4 7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one 
• 63272-91-3 ethyl 2-benzoyl-3-(pyridin-2-yl)acrylate 
• 72742-89-3 3-oxo-3-phenyl-N-(pyridin-3-yl)propanamide 
• 123293-45-8 ethyl α-benzoyl-β-(2-furyl)acrylate 
• 16054-92-5 N-(pyridin-2-yl)-3-oxo-3-phenylpropanamide 
• 23058-90-4 N-(3-methoxyphenyl)-3-oxo-3-phenylpropanamide 
• 101283-65-2 3-oxo-3-phenyl-propionic acid-(2-methylsulfanyl-anilide) 
• 72916-37-1 ethyl 2-benzoyl-3-(3-nitrophenyl)acrylate 
• 33554-46-0 5-hydroxy-7-methyl-2-phenyl-4H-chromen-4-one 
• 15235-99-1 7-hydroxy-5-methylflavone 
• 4850-82-2 ethyl 2-benzoyl-3-oxo-3-phenylpropionate 
• 64267-12-5 7-(methyloxy)-3-(phenylcarbonyl)-2H-chromen-2-one 

Relevant articles and documents

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