13865-21-9

Basic information

• Product Name: Butanoic acid, 2-methyl-4-oxo-, methyl ester
• Synonyms: 2-methyl-4-oxo-butanoic acid methyl ester;methyl 2-methyl-4-oxobutyrate;α-Methyl-β-formylpropionsaeuremethylester;methyl β-formylisobutyrate;methyl 2-methyl-3-formylpropionate
• CAS NO: 13865-21-9
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Mol File: 13865-21-9.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 2-methyl-4-oxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 2-methyl-4-oxo-, methyl ester(13865-21-9)
• EPA Substance Registry System: Butanoic acid, 2-methyl-4-oxo-, methyl ester(13865-21-9)

Safety Data

• Hazardous Substances Data: 13865-21-9(Hazardous Substances Data)

Usage

Description

Butanoic acid, 2-methyl-4-oxo-, methyl ester, also known as Methyl 2-Methyl-4-oxobutanoate, is an organic compound derived from the preparation of amino esters through a rhodium-catalyzed tandem hydroaminomethylation process involving allyl esters and secondary amines/anilines. It is characterized by its unique chemical structure and properties, which make it suitable for various applications across different industries.

Uses

Used in Chemical Synthesis:
Butanoic acid, 2-methyl-4-oxo-, methyl ester is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block for the creation of more complex molecules, contributing to the development of new materials and chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Butanoic acid, 2-methyl-4-oxo-, methyl ester is used as a key component in the development of new drugs. Its specific chemical properties enable it to be incorporated into the molecular structure of potential therapeutic agents, enhancing their efficacy and selectivity.
Used in Flavor and Fragrance Industry:
Butanoic acid, 2-methyl-4-oxo-, methyl ester is also utilized in the flavor and fragrance industry due to its distinct aroma and taste. It can be used to create unique scents and flavors for various products, such as perfumes, cosmetics, and the food industry.
Used in Research and Development:
Butanoic acid, 2-methyl-4-oxo-, methyl ester is employed in research and development settings to study its properties and potential applications. Scientists and researchers use it to explore new reaction pathways, develop novel synthetic methods, and investigate its potential use in various fields, including materials science, pharmaceuticals, and environmental applications.

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 3487, 1982 DOI: 10.1016/S0040-4039(00)87648-0

Upstream product

• 554-12-1 propanoic acid methyl ester 
• 85684-59-9 percarbonate de O,O-t-butyle et O-vinyle 
• 201230-82-2 carbon monoxide 
• 80-62-6 methacrylic acid methyl ester 
• 73372-15-3 methyl 4-hydroxy-2-methylbutanoate 
• 110-91-8 morpholine 
• 130450-06-5 2-(2,2-Dimethoxy-ethyl)-2-methyl-malonic acid dimethyl ester 
• 51534-81-7 dimethyl 2-(2,2-dimethoxyethyl)-1,3-propanedioate 
• 124-41-4 sodium methylate 
• 57976-71-3 trans-2,2-dichloro-3-methylcyclopropanecarbaldehyde 
• 127590-16-3 1-Methyl-2-trimethylsilanyloxy-cyclopropanecarboxylic acid methyl ester 
• 25252-24-8 3-methoxycarbonylbutyraldehyde dimethylacetal 

Downstream Products

• 70423-38-0 (S)-2-methyl-1,4-butandiol 
• 2938-98-9 (R)-2-methylbutane-1,4-diol 
• 73372-15-3 methyl 4-hydroxy-2-methylbutanoate 
• 1679-47-6 3-methyltetrahydro-2-furanone 

Relevant articles and documents

SYNTHESE D'ALDEHYDES γ-FONCTIONNELS PAR VOIE RADICALAIRE

The addition of radicals issued from the solvent to the double bond of O,O-t-butyl and O-vinyl peroxycarbonate results on the free-radical induced decomposition of this peroxyester and offers an original synthetic route for γ-functional aldehydes.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation

Hydroformylation utilizes dihydrogen, carbon monoxide, and a catalyst to transform alkenes into aldehydes. This work applies chiral bisdiazaphospholane (BDP)- and bisphospholanoethane-ligated rhodium complexes to the hydroformylation of a variety of alkenes to produce chiral tetrasubstituted aldehydes. 1,1′-Disubstituted acrylates bearing electron-withdrawing substituents undergo hydroformylation under mild conditions (1 mol % of catalyst/BDP ligand, 150 psig gas, 60 °C) with high conversions and yields of tetrasubstituted aldehydes (e.g., 13:1 regioselectivity, 85% ee, and 99% regioselectivity and >19:1 diastereoselectivity to tetrasubstituted aldehydes at rates >50 catalyst turnovers/hour. NMR studies of the noncatalytic reaction of HRh(BDP)(CO)2 with methyl 1-fluoroacrylate enable interception of tertiary alkylrhodium intermediates, demonstrating migratory insertion to acyl species is slower than formation of secondary and primary alkylrhodium intermediates. Overall, these investigations reveal how the interplay of sterics, electronics, and ring strain are harnessed to provide access to valuable α-tetrasubstituted aldehyde synthetic building blocks by promoting branched-selective hydroformylation.