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

Description

Ethyl benzoylacetate, also known as Benzoylacetic acid ethyl ester, is an ester with a brandy-like odor and sweet, woody, cherry, and phenolic-like flavor. It undergoes microbial reduction by certain yeasts and fungi to form ethyl (S)-3-hydroxy-3-phenylpropionate and can participate in chemical reactions such as Claisen condensation.

Uses

Used in Organic Synthesis:
Ethyl benzoylacetate is used as an intermediate for different organic synthesis processes. It serves as a key component in the preparation of various organic compounds.
Used in Flavor and Fragrance Industry:
Ethyl benzoylacetate is used as a flavoring agent, providing a sweet, cherry, fruity, and berry-like taste with woody and jammy notes. Its taste threshold values make it suitable for use in food and beverage applications.
Used in Chemical Reactions:
Ethyl benzoylacetate is utilized in chemical reactions such as the synthesis of ethyl 2-fluoro-2-benzolyacetate and the preparation of iodonium ylides. These reactions contribute to the development of new chemical compounds and materials.

Preparation

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

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

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

• 1087-97-4 diethyl benzoylmalonate 
• 618-32-6 Benzoyl bromide 
• 105-36-2 ethyl bromoacetate 
• 1071-46-1 hydrogen ethyl malonate 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 
• 109572-65-8 BrMgCH(CO₂Et)2 
• 24346-56-3 2-benzoyl-butyric acid ethyl ester 
• 1137-11-7 1-benzoyl-3,5-dimethyl-1H-pyrazole 
• 127916-11-4 ethyl bezoylacetate oxime 
• 72050-18-1 ethyl 3-methoxy-3-phenyl-2(Z)-propenoate 
• 7732-18-5 water 

Downstream Products

• 21034-21-9 α-benzoyl-γ-butyrolactone 
• 39626-31-8 ethyl 2-benzoyl-3-phenylacrylate 
• 1846-74-8 3-benzoyl-chromen-2-one 
• 117402-91-2 ethyl-2-benzoyl-3,5-diphenyl-5-oxopentanoate 
• 19088-67-6 7-hydroxy-3-(phenylcarbonyl)-2H-chromen-2-one 
• 58792-29-3 3-oxo-1-phenyl-3-piperidin-1-ylpropan-1-one 
• 65847-84-9 β-benzoyloxy-cinnamic acid ethyl ester 
• 141247-91-8 rac-9-(1'-ethoxycarbonyl-2'-phenyl-2'-oxoeth-1'-yl)xanthene 
• 92653-70-8 2-(1-methyl-piperidin-4-yl)-5-phenyl-1,2-dihydro-pyrazol-3-one 
• 113142-82-8 2-benzoyl-4-[2]pyridyl-butyric acid ethyl ester 
• 101089-46-7 1-phenyl-4-pyridin-4-ylbutan-1-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 

Relevant articles and documents

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