4949-44-4

Basic information

• Product Name: Ethyl propionylacetate
• Synonyms: PROPIONYLACETIC ACID ETHYL ESTER;3-oxo-pentanoicacidethylester;Ethyl 3-oxo-n-valerate;Pentanoic acid, 3-oxo-, ethyl ester;3-OXOVALERIC ACID ETHYL ESTER;3-KETOVALERIC ACID ETHYL ESTER;3-KETO-N-VALERIC ACID ETHYL ESTER;ETHYL 3-OXOPENTANOATE
• CAS NO: 4949-44-4
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• EINECS: 225-593-5
• Product Categories: Acetics acid and esters;C6 to C7;Carbonyl Compounds;Esters;Aliphatics;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 4949-44-4.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 83-84 °C12 mm Hg(lit.)
• Flash Point: 172 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.012 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.475mmHg at 25°C
• Refractive Index: n20/D 1.422(lit.)
• Storage Temp.: Refrigerator
• Solubility: Miscible with glacial acetic acid.
• PKA: 10.58±0.46(Predicted)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 970270
• CAS DataBase Reference: Ethyl propionylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl propionylacetate(4949-44-4)
• EPA Substance Registry System: Ethyl propionylacetate(4949-44-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 4949-44-4(Hazardous Substances Data)

Usage

Description

Ethyl propionylacetate is a colorless liquid that serves as an important intermediate in the synthesis of various organic compounds. It is known for its reactivity with tropolone p-toluenesulfonate in the presence of sodium ethoxide, leading to the formation of 3-propionyl-2H-cyclohepta[b]furan-2-one.

Uses

Used in Pharmaceutical Industry:
Ethyl propionylacetate is used as an intermediate for the synthesis of Rosuvastatin, a widely prescribed medication for lowering cholesterol levels in patients with hyperlipidemia.
Used in Chemical Synthesis:
Ethyl propionylacetate is used as a precursor in the preparation of 1-ethyland 1-n-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, which are compounds bearing one or two substituents on the benzene ring. These compounds have potential applications in various fields, including pharmaceuticals and materials science.
Used in Organic Chemistry:
Ethyl propionylacetate is utilized in the synthesis of 3-propionyl-2H-cyclohepta[b]furan-2-one, a compound that can be further modified or used as a building block for the development of new organic molecules with diverse applications.

InChI:InChI=1/C7H12O3/c1-3-6(8)5-7(9)10-4-2/h3-5H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 33279-01-5 3-oxo-pentanenitrile 
• 39580-00-2 1,1-dichloro-pent-1-en-3-one 
• 141-52-6 sodium ethanolate 
• 17448-81-6 ethyl 2-acetyl-3-oxopentanoate 
• 60-29-7 diethyl ether 
• 79-03-8 propionyl chloride 
• 141-78-6 ethyl acetate 
• 21633-77-2 diethyl 2-propionylmalonate 
• 802294-64-0 propionic acid 
• 4303-71-3 triphenylmethyl sodium 
• 105-37-3 Ethyl propionate 
• 10467-10-4 ethylmagnesium iodide 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 104439-88-5 5-ethyl-2-methyl-1-phenyl-1,2-dihydro-pyrazol-3-one 
• 67244-24-0 ethyl 2-propyl-propionylacetate 
• 53939-83-6 6-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one 
• 916319-06-7 5-ethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 37013-86-8 ethyl 4-acetyl-3-ethyl-5-methyl-1H-pyrrole-2-carboxylate 
• 20935-29-9 2-methyl-3-[4-(methoxy)phenyl]cyclopent-2-ene-1-one 
• 23328-64-5 4-ethyl-2,6-dihydroxy-nicotinonitrile 
• 64231-10-3 4-ethyl-7-hydroxy-2H-1-benzopyran-2-one 
• 71-23-8 propan-1-ol 
• 144-62-7 oxalic acid 
• 5734-66-7 2-amino-6-ethylpyrimidin-4-ol 
• 83909-24-4 2,4-Dimethyl-3,5-diphenyl-2-cyclohexen-1-on 
• 5734-66-7 6-ethylisocytosine 
• 34042-00-7 (2SR,3RS)-2-amino-3-hydroxypentanoic acid 

Relevant articles and documents

Enones with Strained Double Bonds. 5. The 2-Methylbicyclonon-1-en-3-one System

Reaction of the bromo ketone 8 with Et3N resulted in the generation of solutions containing the strained enone 9.Enone 9 could be trapped with furan to form Diels-Alder adducts 10 and 11.However, enone 9 was consumed more rapidly in a reaction that formed the dimeric diketone 12.This dimeric product 12 is believed to be formed by an ene reaction (see structure 14) that occurs under mild conditions.

General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand

Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.

Chemoenzymatic asymmetric synthesis of pregabalin precursors via asymmetric bioreduction of β-cyanoacrylate esters using ene-reductases

The asymmetric bioreduction of a library of β-cyanoacrylate esters using ene-reductases was studied with the aim to provide a biocatalytic route to precursors for GABA analogues, such as pregabalin. The stereochemical outcome could be controlled by substrate-engineering through size-variation of the ester moiety and by employing stereochemically pure (E)- or (Z)-isomers, which allowed to access both enantiomers of each product in up to quantitative conversion in enantiomerically pure form. In addition, stereoselectivities and conversions could be improved by mutant variants of OPR1, and the utility of the system was demonstrated by preparative-scale applications.