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Usage

Uses

Used in Flavor and Fragrance Industry:
Methyl 2-methylbutyrate is used as a flavoring agent for imparting a fruity, apple-like taste to various food products and beverages. Its strong fruity odor also makes it suitable for use as a fragrance ingredient in cosmetics and perfumes.
Used in Chemical Synthesis:
Methyl 2-methylbutyrate can be used as a starting material or intermediate in the synthesis of various chemicals, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Solvent Applications:
Due to its solvent properties, Methyl 2-methylbutyrate can be used in various industrial applications, such as cleaning agents, degreasers, and in the production of paints and coatings.
Used in Research and Development:
Methyl 2-methylbutyrate can be utilized in research and development for studying its chemical properties, reactions, and potential applications in various fields, such as material science, pharmaceuticals, and biotechnology.

Preparation

A mixture of esters including methyl-2-methylbutyrate is obtained from isobutene, CO and methanol under pressure, or from butene, CO and an acid catalyst under pressure.

InChI:InChI=1/C6H12O2/c1-4-5(2)6(7)8-3/h5H,4H2,1-3H3

Upstream product

• 41725-90-0 methyl 2-methylbut-2-enoate 
• 34293-67-9 methyl 3-(R)-hydroxy-2-(S)-methylbutanoate 
• 186581-53-3 diazomethane 
• 624-64-6 trans-2-Butene 
• 201230-82-2 carbon monoxide 
• 67-56-1 methanol 
• 5856-79-1 iso-butyl chloroformate 
• 106-99-0 buta-1,3-diene 
• 106-98-9 1-butylene 
• 7664-93-9 sulfuric acid 
• 590-18-1 (Z)-2-Butene 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 116-53-0 2-Methylbutanoic acid 
• 591-50-4 iodobenzene 

Downstream Products

• 13851-08-6 3,5,7,10-tetramethylundec-9-en-4,6-dione 
• 18641-70-8 2,4-Dimethyl-3-pentanone 
• 32444-33-0 methyl 2-ethyl-3-methylbutyrate 
• 5296-70-8 methyl 2-ethyl-2-methylbutyrate 
• 41487-73-4 Methyl-2-ethyl-2-methyloctanoat 
• 3234-80-8 methyl 2-ethyl-2-methylhexanoate 
• 91008-82-1 2-Isopropyl-capronsaeure-methylester 
• 137-32-6 (+/-)-2-methyl-1-butanol 
• 82504-42-5 methyl (2-chloromethyl)butanoate 
• 13888-03-4 methyl 4-chloro-2-methylbutanoate 
• 58308-68-2 methyl 2-chloro-2-methylbutanoate 
• 82504-44-7 chloromethyl 2-methylbutanoate 
• 815-75-8 methyl erythro-3-chloro-2-methylbutanoate 
• 815-75-8 methyl threo-3-chloro-2-methylbutanoate 

Relevant academic research and scientific papers

Synthesis and pyrolysis of two novel pyrrole ester flavor precursors

In order to develop the high-temperature-released pyrrole aroma, two novel flavors precursors of methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate and methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate were synthesized using glucosamine hydrochloride and methyl acetoacetate as raw materials through cyclization, oxidation, alkylation, reduction, and esterification. The target compounds were characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). Thermogravimetry (TG), differential scanning calorimeter (DSC) and the pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) methods were used to analyze the heating-stability of the target compounds, and the pyrolysis mechanism was inferred. Py-GC/MS results indicated that some fragrance compounds were formed during?thermal degradation such as 2-methylbutyric acid, 2-methylbutyrate, alkylpyrroles, and benzoic acid, which were important aroma components or flavor additives. This provided a theoretical reference for the application of pyrrole ester in cigarette and heat-processed food flavoring.

Iron-catalysed 1,2-aryl migration of tertiary azides

1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives

A mCPBA-mediated, metal-free, intramolecular dioxygenation reaction of unactivated alkenes is reported. In the presence of m-chlorobenzoic peracid, different unsaturated amide substrates could be cyclized via epoxide intermediates, producing the corresponding 5-imino-2-tetrahydrofuranyl methanol products in up to 94% yield at room temperature.

Photocatalytic Hydromethylation and Hydroalkylation of Olefins Enabled by Titanium Dioxide Mediated Decarboxylation

A versatile method for the hydromethylation and hydroalkylation of alkenes at room temperature is achieved by using the photooxidative redox capacity of the valence band of anatase titanium dioxide (TiO2). Mechanistic studies support a radical-based mechanism involving the photoexcitation of TiO2 with 390 nm light in the presence of acetic acid and other carboxylic acids to generate methyl and alkyl radicals, respectively, without the need for stoichiometric base. This protocol is accepting of a broad scope of alkene and carboxylic acids, including challenging ones that produce highly reactive primary alkyl radicals and those containing functional groups that are susceptible to nucleophilic substitution such as alkyl halides. This methodology highlights the utility of using heterogeneous semiconductor photocatalysts such as TiO2 for promoting challenging organic syntheses that rely on highly reactive intermediates.

Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand

The invention discloses a method for preparing organic carboxylic ester by combined catalysis of an aryl bidentate phosphine ligand. The method comprises the following steps: under the action of a palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, carrying out a hydrogen esterification reaction on terminal olefin, carbon monoxide and alcohol so as to generate theorganic carboxylic ester with one more carbon than olefin. According to the invention, by adoption of the palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, good catalytic activity and selectivity for the hydrogen esterification reaction of the olefin are achieved, and olefin carbonylation to synthesize organic carboxylic ester can be efficiently catalyzed. Thearyl bidentate phosphine ligand has a rigid skeleton structure of a rigid ligand and the flexibility of a flexible ligand, so the aryl bidentate phosphine ligand has proper flexibility due to the characteristic that the aryl bidentate phosphine ligand is soft and rigid, and a most favorable coordination mode and a stable active structure in space are favorably formed. In addition, the aryl bidentate phosphine ligand has the advantages of high stability, simple and convenient synthesis method and the like; and a novel industrial technology is provided for production of organic carboxylate compounds.

Acid-catalyzed oxidation of levulinate derivatives to succinates under mild conditions

Levulinate derivatives are an attractive platform for the production of renewable chemicals. Here we report on the oxidation of methyl levulinate into dimethyl succinate with peroxides under mild conditions using Br?nsted and Lewis acid catalysts. Selectivities to succinate and acetate derivatives of approximately 60 and 40 %, respectively, were obtained with strong Br?nsted acids in methanol. Although the molecular structure (i.e., carbon-chain length and branching around the C=O group) and the oxidant type affect the product distribution, solvent choice has the strongest impact on changing the location of oxygen insertion into the carbon backbone. Specifically, switching the solvent from methanol to heptane resulted in a decrease in the succinate/acetate ratio from 1.6 to 0.3. In contrast to Br?nsted acids, we demonstrate that the nature of the metal cation is responsible for changing the reaction selectivity of water-tolerant Lewis acidic triflate salts.

Carbogallation of alkynes using gallium tribromide and silyl ketene acetals and synthetic application to cross-coupling with aryl iodides

Try substituted alkynes with GaBr3: The regio- and stereoselective carbogallation of alkynes has been achieved by a simple treatment of GaBr3, alkynes, and ketene silyl acetals. The produced alkenylgallium compounds can be used for the synthesis of selective trisubstituted alkenes through successive cross-coupling with aryliodides (see scheme). The usability of the carbogallation was presented by the total synthesis of meroterpenoid nodosol, which was extracted from the seagrass Cymodocea nodosa. Copyright

Oxidation of β-dicarbonyl compounds with tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate

Oxidation of β-dicarbonyl compounds with tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate (benzene, 20°C) involves the activated methylene group with intermediate formation of trioxo derivatives and is accompanied by decomposition of carbon skeleton. The oxidation products are carbon dioxide, carboxylic acids, and tert-butyl and peroxy esters derived from the latter.

Homogeneous asymmetric hydrogenation catalyst

Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.

A cytotoxic and apoptosis-inducing sesquiterpenoid isolated from the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk)

Repeated silica gel and octadecyl silica gel (ODS) column chromatography of the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk) led to the isolation of a new sesquiterpenoid, 3-((S)-2-methylbutyryloxy)-costu-1(10),4(5)- dien-12,6α-olide (2), along with two previously reported sesquiterpenoids: 8α-angeloyloxy-3β,4β-epoxy-6βH,7αH,8βH-guaia- 1(10),11(13)-dien-12,6α-olide (1, carlaolide B) and 3β,4β-epoxy- 8α-isobutyryloxy-6βH,7αH,8βH-guaia-1(10),11(13)-dien-12, 6α-olide (3, carlaolide A). The structure of compound 2 was elucidated by spectroscopic data analysis, including one dimensional (1D) and two dimensional (2D) nuclear magnetic resonance (NMR) experiments. Of the isolates, compound 2 exhibited potent cytotoxicity against human cervix adenocarcinoma cells and induced apoptosis.