93-58-3

Usage

Chemical Description

Methyl benzoate is an ester with the chemical formula C8H8O2, commonly used as a flavoring agent.

InChI:InChI=1/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 109-02-4 4-methyl-morpholine 
• 67-56-1 methanol 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 98-91-9 thiobenzoic acid 
• 108-86-1 bromobenzene 
• 115-10-6 Dimethyl ether 
• 98-08-8 α,α,α-trifluorotoluene 
• 774-65-2 benzoic acid tert-butyl ester 
• 124-41-4 sodium methylate 
• 533-01-7 copper(II) benzoate 

Downstream Products

• 7666-04-8 2-methylsulfanyl-1H-imidazole 
• 2315-68-6 propyl benzoate 
• 1565-71-5 3-phenylpentan-3-ol 
• 120-51-4 benzoic acid benzyl ester 
• 6324-60-3 Bis(2-methylphenyl)phenylmethanol 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 52161-54-3 2,5-diphenyl-hex-2-ene 
• 31719-77-4 3-chloromethylbenzoic acid 
• 34040-63-6 methyl 3-(chloromethyl)benzoate 
• 100-47-0 benzonitrile 
• 13988-67-5 benzoylpivaloylmethane 
• 6963-55-9 2-methyl-2-butyl benzoate 
• 720-75-2 methyl 4-phenylbenzoate 
• 83527-96-2 methyl 3’-nitro-[1,1’-biphenyl]-2-carboxylate 

Relevant academic research and scientific papers

Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources

Ni/photoredox catalysis has emerged as a powerful platform for C(sp2)–C(sp3) bond formation. While many of these methods typically employ aryl bromides as the C(sp2) coupling partner, a variety of aliphatic radical sources have been investigated. In principle, these reactions enable access to the same product scaffolds, but it can be hard to discern which method to employ because nonstandardized sets of aryl bromides are used in scope evaluation. Herein, we report a Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides where benzaldehyde di(alkyl) acetals serve as alcohol-derived radical sources. Reaction development, mechanistic studies, and late-stage derivatization of a biologically relevant aryl chloride, fenofibrate, are presented. Then, we describe the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chemical space of the substrate class. By superimposing scope examples from published Ni/photoredox methods on this same chemical space, we identify areas of sparse coverage and high versus low average yields, enabling comparisons between prior art and this new method. Additionally, we demonstrate that the systematically selected scope of aryl bromides can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning.

Aerobic oxidative cleavage and esterification of C[dbnd]C bonds catalyzed by iron-based nanocatalyst

Functionalization of C[dbnd]C bonds by oxidative cleavage plays an important role in organic synthesis. However, the traditional functionalized products are mainly aldehydes, ketones and carboxylic acids, and the substrates are limited to examples of active aromatic olefins with very scarce inactive olefins. Herein we disclose an efficient protocol for the direct formation of esters by oxidative cleavage of C[dbnd]C bonds using heterogeneous iron nanocomposite catalyst supported on nitrogen-doped carbon materials with molecular oxygen and tert-butylhydroperoxide (TBHP) as the oxidants. The results show that molecular oxygen as the terminal oxidant is mainly responsible for the cleavage process, and that the auxiliary oxidant TBHP promotes the formation of the intermediate epoxide, thus increasing the selectivity of the product. The catalytic system has a wide range of substrate compatibility involving the challenging inactive aliphatic and long-chain alkyl aryl olefins. The catalyst was reused seven times with no loss in catalytic activity. Characterization and control experiments uncover that the core-shell Fe and Fe3C nanoparticles encapsulated by graphitic carbon play a predominant role in catalyzing the oxidative cleavage of olefins to esters. Preliminary mechanistic studies disclose that this process involves both free radical reactions and tandem sequential reactions.

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.

Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis

Carboxyl methyltransferase (CMT) enzymes catalyse the biomethylation of carboxylic acids under aqueous conditions and have potential for use in synthetic enzyme cascades. Herein we report that the enzyme FtpM from Aspergillus fumigatus can methylate a broad range of aromatic mono- and dicarboxylic acids in good to excellent conversions. The enzyme shows high regioselectivity on its natural substrate fumaryl-l-tyrosine, trans, trans-muconic acid and a number of the dicarboxylic acids tested. Dicarboxylic acids are generally better substrates than monocarboxylic acids, although some substituents are able to compensate for the absence of a second acid group. For dicarboxylic acids, the second methylation shows strong pH dependency with an optimum at pH 5.5–6. Potential for application in industrial biotechnology was demonstrated in a cascade for the production of a bioplastics precursor (FDME) from bioderived 5-hydroxymethylfurfural (HMF).

Preparation method of methyl benzoate compound

A preparation method of a methyl benzoate compound comprises the step that the methyl benzoate compound is prepared by carrying out esterification reaction on a benzoic acid compound and methyl alcohol under the catalysis of dihalogen hydantoin, and the molar ratio of the benzoic acid compound to the dihalogen hydantoin to the methyl alcohol is 1: (0.01-0.4): (2-30). According to the preparation method, the methyl benzoate compound can be efficiently prepared under mild conditions, the operation is safe, no acid waste liquid exists, meanwhile, raw materials are easy to obtain, and the production cost is low.

Design, synthesis, in vitro determination and molecular docking studies of 4-(1-(tert-butyl)-3-phenyl-1H-pyrazol-4-yl) pyridine derivatives with terminal sulfonamide derivatives in LPS-induced RAW264.7 macrophage cells

In the present work, a new series of 4-(1-(tert-butyl)-3-phenyl-1H-pyrazol-4-yl) pyridine possessing terminal ethyl or propyl sulfonamides was designed and synthesized. The cytotoxic effect of the final compounds was measured by applying MTT assay in LPS-Induced RAW264.7 macrophage cells. The final target compounds were screened for their anti-inflammatory effect through their ability to inhibit NO and PGE2 production and cytokines production (TNF-α, IL-6, IL-1β) in LPS-induced RAW264.7 macrophage at 10 μM concentration. Compounds 8d, 9d, and 9k showed the highest inhibitory effect on NO production. Compounds 8d and 9k exhibited high PGE2 inhibition with IC50 values of 3.47, 2.54 μM, respectively. Compounds 8d and 9k exhibited high cytokines inhibition ≥60%. The most potent compounds 8d and 9k were tested to determine their effect on iNOS and COX-2 mRNA expression level. Compound 9k activity on iNOS and COX-2 proteins level, pro-inflammatory mediators and cytokines was determined and showed remarkable inhibition for both proteins level. Compounds 8d, 9k showed high binding affinity to COX-2 active site and exhibited similar binding interactions of the native ligand celecoxib. [Figure not available: see fulltext.]

Method for preparing N6-benzoyladenosine

The invention discloses a method for preparing N6-benzoyladenosine. The method comprises the following steps: (1) weighing and adding adenosine and a protectant in a flask, adding a solvent and a catalyst, carrying out stirring refluxing for a period of t

Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin

We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.55.0 equiv) in toluene at 6080 °C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 °C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.

Tunable aryl imidazolium ionic liquids (TAIILs) as environmentally benign catalysts for the esterification of fatty acids to biodiesel fuel

Herein, we describe the synthesis of tunable aryl imidazolium ionic liquid catalysts and tested for esterification of fatty acids to biodiesel. In this work, six tunable aryl imidazolium ionic liquids (TAIILs) 1a-1f were prepared. These ionic liquids were used as the economical and reusable catalysts for the synthesis of biodiesel fuels. The reaction has been preceded in a monophase at 80 °C for 4 h, after which the product was separated from the catalyst system by a simple liquid/liquid phase separation at room temperature with excellent yields. With the simple post-process, the catalyst is reusable at least 6 times. This novel method offers a short reaction time, good yields, and environmentally benign characteristics.