13865-19-5

Basic information

• Product Name: Methyl 4-oxobutanoate
• Synonyms: 4-OXOBUTANOIC ACID METHYL ESTER;methyl 4-oxobutyrate;Succinaldehydic acid, methyl ester;3-Formylpropanoic acid methyl ester;4-Oxobutyric acid methyl ester;Einecs 237-611-9;Butanoic acid, 4-oxo-, Methyl ester;Methyl 4-oxobutanoate(Methyl 3-ForMylpropionate)
• CAS NO: 13865-19-5
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.12
• EINECS: 237-611-9
• Product Categories: Aldehydes;C1 to C6;Carbonyl Compounds
• Mol File: 13865-19-5.mol
• Article Data: 94

Chemical Properties

• Boiling Point: 187-188 °C(lit.)
• Flash Point: 187 °F
• Appearance: Reddish brown viscous liquid
• Density: 1.109 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.71mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Methyl 4-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-oxobutanoate(13865-19-5)
• EPA Substance Registry System: Methyl 4-oxobutanoate(13865-19-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 13865-19-5(Hazardous Substances Data)

Usage

Description

Methyl 4-oxobutanoate, also known as methyl-4-oxobutyrate, is an oxobutyrate derivative that serves as an important industrial intermediate. It is widely utilized in the synthesis of various industrial compounds and as a model substrate for exploring the asymmetric Henry reaction, which allows for the assembly of a stereodefined lactam with high efficiency and enantiomeric purity.

Uses

Used in Pharmaceutical Industry:
Methyl 4-oxobutanoate is used as a starting material for the synthesis of (-)-deoxoprosophylline, a piperidine alkaloid with therapeutic potential. This application highlights its importance in the development of new pharmaceutical compounds.
Used in Chemical Industry:
Methyl 4-oxobutanoate is used as an intermediate in the preparation of important industrial compounds such as gamma-butyrolactone, 1,4-butanediol, and glutamate. Its role in the synthesis of these compounds makes it a valuable component in the chemical industry.
Used in Research and Development:
Methyl 4-oxobutanoate is used as a model substrate for exploring the asymmetric Henry reaction. This application is crucial for advancing the understanding of asymmetric synthesis and the development of new, more efficient methods for producing enantiomerically pure compounds.

References

Gresham, William F, R. E. Brooks, and W. M. Bruner. "Preparation of methyl 4-oxobutyrate." US2549454. 1951. Murib, Jawad H, and W. D. Baugh. "Process for the preparation of methyl 4-oxobutyrate and its methanol addition products." US, US5072005. 1991. https://www.scbt.com/scbt/product/methyl-4-oxobutanoate-13865-19-5

InChI:InChI=1/C5H8O3/c1-8-5(7)3-2-4-6/h4H,2-3H2,1H3

Upstream product

• 62435-72-7 2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester 
• 1490-25-1 succinic acid monomethylester chloride 
• 186581-53-3 diazomethane 
• 692-29-5 Succinic semialdehyde 
• 4220-66-0 methyl 4,4-dimethoxybutanoate 
• 31722-42-6 Dimethyl hydroxymethylensuccinat 
• 67-56-1 methanol 
• 292638-85-8 acrylic acid methyl ester 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 818-57-5 Methyl 4-pentenoate 
• 13013-02-0 methyl 4-nitrobutyrate 
• 925-57-5 methyl 4-hydroxybutanoate 
• 90288-79-2 methyl 3-(trimethylsiloxy)-1-cyclopropanecarboxylate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 105-21-5 4-propylbutanolide 
• 617-65-2 Glutamic acid 
• 95691-14-8 4-(Benzhydryl-amino)-4-hydroxyphosphinoyl-butyric acid methyl ester 
• 35848-90-9 4,4-dimethoxybutan-1-oic acid 
• 115205-07-7 di-tert-butyl 3-((hydroxycarbonyl)methyl)-1-cyclohexene-1,5-dicarboxylate 
• 112081-57-9 3-((2S,3R,4S,5R)-3,4-Dimethyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 112081-60-4 3-((2S,3R,4S,5S)-3,4-Dimethyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 112081-59-1 3-((2S,3R,4S,5R)-3-Cyclohexyl-4-methyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 153393-25-0 methyl 1-benzyl-4-oxo-2-imidazolidinepropanoate 
• 101853-52-5 (S)-4-Hydroxy-hexanoic acid methyl ester 
• 112375-44-7 (Z)-methyl 6-methylhept-4-enoate 
• 112081-58-0 3-((2S,3R,4S,5R)-3-Isopropyl-4-methyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 120056-44-2 cis-(1R,3R)-(+)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 84129-60-2 trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 

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