547-63-7

Usage

Uses

1. Flavoring Agent:
Methyl isobutyrate is used as a flavoring agent in the food and beverage industry due to its sweet, ethereal, fruity, and juicy fruit taste characteristics at 35 ppm. It is commonly found in Russian champagnes and among the volatile components of strawberry juice, as well as in apple juice, banana, kumquat peel oil, blueberry, melon, papaya, pineapple, fried potato, starfruit, dill herb, cherimoya, kiwifruit, loquat, naranjilla fruit, and cape gooseberry.
2. Solvent and Organic Synthesis:
Methyl isobutyrate can be used as a solvent and in organic synthesis processes due to its chemical properties and solubility in common organic solvents.
3. Gas Chromatography Standard:
Methyl isobutyrate is used as a standard for gas chromatography, a technique used to separate and analyze volatile compounds in a mixture.
4. Mass Spectrometry Studies:
Radiofrequency-induced plasmas of methyl isobutyrate have been studied using mass spectrometry, which is a technique used to identify and quantify compounds based on their mass-to-charge ratio.

Preparation

Methyl isobutyrate can be synthesized by direct esterification of methanol with isobutyric acid.

Carcinogenicity

Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.

InChI:InChI=1/C5H10O2/c1-4(2)5(6)7-3/h4H,1-3H3

Upstream product

• 67-56-1 methanol 
• 78-83-1 2-methyl-propan-1-ol 
• 74-96-4 ethyl bromide 
• 24985-51-1 (Z)-4-methoxy-5-methyl-hex-3-en-2-one 
• 38923-57-8 methyl 2,2-dimethyl-3-oxobutanoate 
• 60-29-7 diethyl ether 
• 1068-55-9 isopropylmagnesium chloride 
• 79-22-1 methyl chloroformate 
• 80-62-6 methacrylic acid methyl ester 
• 79-31-2 isobutyric Acid 
• 107-31-3 Methyl formate 
• 2589-57-3 dimethyl 2,2'-azobis(isobutyrate) 
• 71-43-2 benzene 
• 108-95-2 phenol 

Downstream Products

• 78-82-0 Isobutyronitrile 
• 292638-85-8 acrylic acid methyl ester 
• 5162-48-1 2,2,4-trimethyl-3-pentanol 
• 59742-51-7 methyl 2,4-dimethyl-3-oxopentanoate 
• 34553-37-2 methyl 5-methyl-4-oxohexanoate 
• 594-60-5 2,3-dimethylbutan-2-ol 
• 54775-01-8 4-isopropyl-2,6-dimethyl-heptan-4-ol 
• 563-83-7 ISOPROPYLAMIDE 
• 22779-89-1 isobutyrohydroxamic acid 
• 80-62-6 methacrylic acid methyl ester 
• 53673-16-8 N-(2-aminoethyl)isobutyramide 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 68039-27-0 methyl 2-ethyl-3-oxohexanoate 
• 59906-54-6 2,5-dimethyl-4-nitro-3-hexanone 

Relevant academic research and scientific papers

Boosting homogeneous chemoselective hydrogenation of olefins mediated by a bis(silylenyl)terphenyl-nickel(0) pre-catalyst

The isolable chelating bis(N-heterocyclic silylenyl)-substituted terphenyl ligand [SiII(Terp)SiII] as well as its bis(phosphine) analogue [PIII(Terp)PIII] have been synthesised and fully characterised. Their reaction with Ni(cod)2(cod = cycloocta-1,5-diene) affords the corresponding 16 VE nickel(0) complexes with an intramolecularη2-arene coordination of Ni, [E(Terp)E]Ni(η2-arene) (E = PIII, SiII; arene = phenylene spacer). Due to a strong cooperativity of the Si and Ni sites in H2activation and H atom transfer, [SiII(Terp)SiII]Ni(η2-arene) mediates very effectively and chemoselectively the homogeneously catalysed hydrogenation of olefins bearing functional groups at 1 bar H2pressure and room temperature; in contrast, the bis(phosphine) analogous complex shows only poor activity. Catalytic and stoichiometric experiments revealed the important role of the η2-coordination of the Ni(0) site by the intramolecular phenylene with respect to the hydrogenation activity of [SiII(Terp)SiII]Ni(η2-arene). The mechanism has been established by kinetic measurements, including kinetic isotope effect (KIE) and Hammet-plot correlation. With this system, the currently highest performance of a homogeneous nickel-based hydrogenation catalyst of olefins (TON = 9800, TOF = 6800 h?1) could be realised.

Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst

A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.

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.

PH-Responsive Pickering emulsion stabilized by polymer-coated silica nanoaggregates and applied to recyclable interfacial catalysis

We first synthesized a diblock copolymer poly[tert-butyl methacrylate]-b-poly[3-(trimethoxysilyl)propyl methacrylate] (PtBMA-b-PTMSPMA) through reversible addition-fragmentation chain transfer (RAFT) living radical polymerization and grafted it onto fumed silica by converting the PTMSPMA segment to silanol and the PtBMA segment to polymethylacrylic acid (PMAA) in the presence of trifluoroacetic acid in order to obtain PMAA brush-coated silica nanoaggregates P-Si. TEM, DLS, FTIR, and TGA results confirmed the successful modification of the starting materials. The nanoaggregates flocculated and stabilized a toluene-in-water Pickering emulsion at low pH, while the nanoaggregates were well dispersed in water and broke the emulsion under both neutral and basic conditions. Alternatively, the addition of acid/base induced emulsification/demulsification cycles that were sustained for several cycles. Moreover, when the P-Si was mixed with Rh-loaded silica, Rh-Si, the mixture had the same pH-responsive Pickering emulsion behavior as the single P-Si. This Pickering emulsion system can be used in the biphasic interfacial catalytic hydrogenation of olefins and had excellent yields under a hydrogen atmosphere. The yield of Pickering emulsion catalysis rapidly reached more than 99% in 3 h, while that of the demulsified mixture failed to reach 20% in 4 h, which verified the promotion of catalysis by the Pickering emulsion. Base-induced demulsification can be used to separate the products and recycle the catalyst. This pH-responsive Pickering emulsion catalytic system was capable of several cycles of reuse, and there was no significant decrease in catalytic efficiency even after eight cycles. This journal is

Process for the production of esters

A process for making methyl esters in high yields. The process comprises contacting aliphatic or aromatic aldehydes and methanol with a homogeneous dimeric ruthenium catalyst, to catalyze the dehydrogenative coupling between aliphatic or aromatic aldehydes and methanol. The reaction is highly selective (99.9%) toward the formation of methyl esters over homoesters and alcohols and operates at temperatures of less than 100° C. for 2-8 hours.

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.

Selective hydrogenation of α,β-unsaturated carbonyl compounds on silica-supported copper nanoparticles

Silica-supported copper nanoparticles prepared via surface organometallic chemistry are highly efficient for the selective hydrogenation of various α,β-unsaturated carbonyl compounds yielding the corresponding saturated esters, ketones, and aldehydes in the absence of additives. High conversions and selectivities (>99%) are obtained for most substrates upon hydrogenation at 100-150 °C and under 25 bar of H2.

Synthesis of β2,2-Amino Esters via Rh-Catalysed Regioselective Hydroaminomethylation

The synthesis of β2,2-amino esters was successfully achieved via Rh-catalysed regioselective hydroaminomethylation of methyl methacrylate with secondary amines using the neutral precursor [Rh(acac)(CO)2]. In this process, the presence of molecular sieves revealed crucial in order to access the final amino ester. For the synthesis of products containing aniline derivatives, the use of the cationic precursor [Rh(COD)2]BF4 and MeCgPPh phosphine as ligand was necessary in a mixture of toluene/DCE as solvent. Effects of the steric and electronic properties of the amines were observed during this study. Interestingly, poisoning effect of CO in the hydrogenation of the imine intermediate was observed when benzyl amine was used. (Figure presented.).

The Effect of Viscosity on the Diffusion and Termination Reaction of Organic Radical Pairs

The effect of viscosity on the diffusion efficiency (Fdif) of an organic radical pair in a solvent cage and the termination mechanism, that is, the selectivity of disproportionation (Disp) and combination (Comb) of the geminated caged radical pair and the diffused radicals encountered, were investigated quantitatively by following the photolysis of dimethyl 2,2′-azobis(2-methylpropionate) (V-601) in the absence and presence of PhSD. Fdif and Disp/Comb selectivity outside the cage [Disp(dif)/Comb(dif)] are highly sensitive to the viscosity. In contrast, the Disp/Comb selectivity inside the cage [Disp(cage)/Comb(cage)] is rather insensitive. The difference in viscosity dependence between Disp(cage)/Comb(cage) and Disp(dif)/Comb(dif) is explained by the spin state of the radical pair inside and outside the cage and the spin state dependent configurational changes of the radical pair upon their collision. Given that the configurational change of the radicals associates the displacement and reorganization of solvents around the radicals, the termination outside the cage, which requires larger change than that inside the cage, is highly viscosity dependent. Furthermore, while the bulk viscosity of each solvent shows good correlation with Fdif and Disp/Comb selectivity, microviscosity is the better parameter predicting Fdif and Disp(dif)/Comb(dif) selectivity regardless of the solvents.