13984-57-1

Basic information

• Product Name: ETHYL 4-ACETYLBUTYRATE
• Synonyms: 5-Oxohexanoic acid ethyl ester;5-oxo-hexanoicaciethylester;Ethyl 5-oxohexanoate;ETHYL 4-ACETYLBUTYRATE;4-Acetylbutyricacidethylester;Hexanoic acid, 5-oxo-, ethyl ester;Ethyl 4-acetylbutanoate;5-Ketocaproic acid ethyl ester
• CAS NO: 13984-57-1
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• EINECS: 237-776-7
• Product Categories: Plasticizers;Polymer Additives;Polymer Science
• Mol File: 13984-57-1.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 221-222 °C(lit.)
• Flash Point: 157 °F
• Appearance: /
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.103mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• BRN: 1762625
• CAS DataBase Reference: ETHYL 4-ACETYLBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-ACETYLBUTYRATE(13984-57-1)
• EPA Substance Registry System: ETHYL 4-ACETYLBUTYRATE(13984-57-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 13984-57-1(Hazardous Substances Data)

Usage

Description

ETHYL 4-ACETYLBUTYRATE, also known as 5-Oxohexanoic Acid Ethyl Ester, is a versatile synthetic intermediate with a wide range of applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
ETHYL 4-ACETYLBUTYRATE is used as a synthetic intermediate for the preparation of tyrosine-derived RGD peptidomimetics containing oligoethylene glycol (OEG) spacers. These peptidomimetics are essential in the development of targeted drug delivery systems and have potential applications in cancer therapy and other medical treatments.
Used in Chemical Synthesis:
ETHYL 4-ACETYLBUTYRATE is also used to synthesize constrained glycyl amides derived from RGD tripeptide. These constrained glycyl amides serve as nonpeptide αvβ3 antagonists, which have potential applications in the development of new drugs targeting specific biological processes and pathways.

InChI:InChI=1/C8H14O3/c1-3-11-8(10)6-4-5-7(2)9/h3-6H2,1-2H3

Upstream product

• 191171-80-9 2-acetyl-glutaric acid-5-ethyl ester-1-tert-butyl ester 
• 64-17-5 ethanol 
• 3128-06-1 5-ketohexanoic acid 
• 123-54-6 acetylacetone 
• 140-88-5 ethyl acrylate 
• 34495-74-4 Ethyl 4-hexenoate 
• 4761-26-6 ethyl 2-carbethoxy-5-oxocaproate 
• 78-94-4 methyl vinyl ketone 
• 927-80-0 1-ethoxyacetylene 
• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 
• 18295-66-4 1-ethoxy-1-(trimethylsiloxy)ethene 
• 1120-72-5 2-Methylcyclopentanone 
• 5205-39-0 ethyl glutaroyl chloride 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 69578-88-7 5-[(6-chloro-pyridazin-3-yl)-hydrazono]-hexanoic acid ethyl ester 
• 83912-17-8 Ethyl 5-hydroxy-5-(p-tolyl)hexanoate 
• 2610-95-9 6,6-dimethyltetrahydro-2H-pyran-2-one 
• 20266-62-0 Ethyl 5-hydroxyhexanoate 
• 928-40-5 hexane-1,5-diol 
• 629643-45-4 6-(2-nitro-phenyl)-5-oxo-hexanoic acid ethyl ester 
• 28591-18-6 5-(4-methylphenyl)hexan-1-ol 
• 70329-63-4 (+/-)-5,6-dehydrosenedigitalene 
• 78518-93-1 5-(p-Tolyl)-hexanal 
• 75227-11-1 Ethyl 5-(p-tolyl)hexanoate 
• 10408-15-8 6-methylhept-6-en-2-one 
• 96849-99-9 ethyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate 
• 1004750-70-2 diethyl (2S,3R)-3-acetyl-2-(p-methoxyphenylamino)hexanedioate 
• 3128-06-1 5-ketohexanoic acid 

Relevant articles and documents

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Oxidation of cyclohexanone and/or cyclohexanol catalyzed by Dawson-type polyoxometalates using hydrogen peroxide

The oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture using as catalyst, Dawson-type polyoxometalates (POMs) of formula, α- and β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 and hydrogen peroxide, carried out at 90 °C with a reaction time of 20 h, led to a high number of mono- and di-acids which were identified by GC-MS. Levulinic, 6-hydroxyhexanoic, adipic, glutaric and succinic acids, major products were evaluated by HPLC. Regardless of the substrate nature, all POMs exhibited high catalytic activity with 94–99% of conversion, whereas the formation of the different products is sensitively related to both the composition and symmetry of the POMs and the substrate nature. The main products are adipic acid in the presence of α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62, levulinic acid in the presence of α1-K7P2Mo5VW12O62 and β-K6P2W18O62 and 6-hydroxyhexanoic acid in the presence of α- and β-K6P2W18O62. Graphical abstract: High catalytic activity was observed with?α- and?β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 Dawson-type for the oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture, in the hydrogen peroxide presence, to several oxygenated products. Adipic, levulinic and 6-hydroxyhexanoic acids are the main products. The peroxo- species formed in situ could be the active sites.[Figure not available: see fulltext.]

Synthesis method of 4-acetyl butyrate compound

The invention discloses a synthetic method of a 4-acetyl butyrate compound, and relates to the technical field of chemical synthesis, and the synthetic method comprises the following steps: taking acetone as a reaction solvent and a reactant to react with an acrylate compound under the catalytic action of tetrahydropyrrole; and after the reaction is finished, carrying out post-treatment on the reaction liquid to prepare the 4-acetyl butyrate compound. The method has the advantages of simple reaction system, environment friendliness, cheap and easily available raw materials, simple post-treatment operation, and no need of column chromatography purification, and is beneficial for industrial production.

An efficient method for retro-Claisen-type C-C bond cleavage of diketones with tropylium catalyst

The retro-Claisen reaction is frequently used in organic synthesis to access ester derivatives from 1,3-dicarbonyl precursors. The C-C bond cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Br?nsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of 1,3-dicarbonyl compounds.