120-33-2

Usage

Uses

Used in Chemical Synthesis:
Ethyl 3-methylbenzoate is used as an intermediate in the chemical synthesis industry for the production of various compounds. Its ability to undergo different chemical reactions makes it a valuable component in the synthesis of pharmaceuticals, fragrances, and other specialty chemicals.
Ethyl 3-methylbenzoate is used as a chemical intermediate for the synthesis of [specific compounds or products] because of its [unique chemical properties or reactivity].

InChI:InChI=1/C10H12O2/c1-3-12-10(11)9-6-4-5-8(2)7-9/h4-7H,3H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 620-22-4 3-Methylbenzonitrile 
• 99-04-7 m-Toluic acid 
• 16544-46-0 ethyl (E)-3-acetyloxy-2-propenoate 
• 78-79-5 isoprene 
• 108-40-7 toluene-3-thiol 
• 201230-82-2 carbon monoxide 
• 625-95-6 3-Iodotoluene 
• 1711-06-4 3-Methylbenzoyl chloride 
• 16331-64-9 ethanolate 
• 36718-84-0 4-nitrophenyl 3-methylbenzoate 
• 24398-88-7 ethyl 3-bromobenzoate 
• 108-41-8 1-chloro-3-methylbenzene 
• 1906-57-6 potassium monoethyl oxalate 

Downstream Products

• 5208-37-7 8-hydroxy-m-cymene 
• 107519-71-1 2-(m-tolyl)benzofuran-3-carbonitrile 
• 6922-90-3 (3-methylphenyl)(diphenyl)methanol 
• 41882-53-5 N-benzyl-3-methylbenzamide 
• 59826-44-7 1,3-di-(m-tolyl)propane-1,3-dione 
• 53882-81-8 (3-methylbenzoyl)acetonitrile 
• 30880-71-8 3-(2-Chloro-4-nitro-phenoxymethyl)-benzoic acid ethyl ester 
• 620-23-5 m-tolyl aldehyde 
• 620-22-4 3-Methylbenzonitrile 
• 587-03-1 3-methylbenzyl alcohol 
• 500707-39-1 3-methyl-1-[3-(tetrahydro-pyran-2-yloxy)-propyl]-cyclohexa-2,5-dienecarboxylic acid ethyl ester 
• 187390-41-6 1-(3-Methylphenyl)-2-[5-methyl-1,3,4-thiadiazol-2-yl]ethanon 
• 460079-58-7 2-(6-chloro-2-pyridinyl)-1-(3-methylphenyl)ethanone 
• 585-74-0 3-Methylacetophenone 

Relevant academic research and scientific papers

A continuous-flow approach to palladium-catalyzed alkoxycarbonylation reactions

Using a continuous-flow approach, it is possible to perform alkoxycarbonylation reactions of aryl iodides. Optimized reactor design allows for adequate mixing of gaseous and liquid reagents. Reactions are performed at rates of around 3 mL/min and at concentrations of 1 M, allowing for significant volumes to be processed per unit time. Palladium acetate (0.5 mol %) is used as the catalyst without the need for an additional ligand.

A 4 + 4 strategy for synthesis of zeolitic metal-organic frameworks: An indium-MOF with SOD topology as a light-harvesting antenna

A zeolitic metal-organic framework with a SOD topology, (Et 2NH2)[In(BCBAIP)]·4DEF·4EtOH (H 4BCBAIP: 5-(bis(4-carboxybenzyl)amino)isophthalic acid) (1), has been constructed by a 4 + 4 synthetic strategy from tetrahedral organic building units and In3+ ions. Compound 1 could adsorb organic dyes and be used as a light-harvesting antenna.

Palladium-catalyzed cross-coupling reaction of arylboronic acids with chloroformate or carbamoyl chloride

The first palladium-catalyzed cross-coupling reaction between substituted arylboronic acids and chloroformate or carbamoyl chloride is described. One-carbon homologation from arylboronic acids was achieved to give corresponding esters or amides in good yi

Desulfurization and Carbonylation of Mercaptans

The first examples of the carbonylation of mercaptans are described: cobalt carbonyl catalyzes the desulfurization and carbonylation of mercaptans to carboxylic esters by means of carbon monoxide in aqueous alcohol.

Continuous-flow, palladium-catalysed alkoxycarbonylation reactions using a prototype reactor in which it is possible to load gas and heat simultaneously

A prototype tube-in-tube reactor in which it is possible to load gas and heat simultaneously has been used in a continuous-flow approach to alkoxycarbonylation reactions of aryl iodides. In the stainless steel coil, liquid flows on the outside of a gas-permeable membrane. The coil can be heated and the temperature can be measured accurately via a probe touching the outer steel surface. A range of aryl iodides can be transformed to the corresponding esters in excellent conversion by reaction at 120 °C using 0.5 mol% palladium acetate as the catalyst with no additional ligand required. Small-scale optimization and substrate screening runs were followed by scale-up.

Base-induced cyclization of derivatives of bispropargylated acetic acid to m -toluic acid

A base-induced cyclization reaction of 1,1-bispropargyls has been examined. Alkali treatment of 2,2-bispropynyl acetic acid derivatives in aqueous ethanol mostly provided 3-methylbenzoic acid. Investigations on substituent effects indicate the requirement of an electron-withdrawing group causing CH acidity and the center of the dipropargylic structure. Besides, an intramolecular hydrogen transfer causing the rearrangement of one terminal alkyne into a corresponding allene appears to be essential. Despite an unsatisfying conversion yield of below 40%, the reaction is interesting due to the mild cyclization conditions.

Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests

To improve the insecticidal activity of (+)-nootkatone, a series of 42 (+)-nootkatone thioethers containing 1,3,4-oxadiazole/thiadiazole moieties were prepared to evaluate their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal evaluation revealed that most of the title derivatives exhibited more potent insecticidal activities than the precursor (+)-nootkatone after the introduction of 1,3,4-oxadiazole/thiadiazole on (+)-nootkatone. Among all of the (+)-nootkatone derivatives, compound 8c (1 mg/mL) exhibited the best growth inhibitory (GI) activity against M. separata with a final corrected mortality rate (CMR) of 71.4%, which was 1.54- and 1.43-fold that of (+)-nootkatone and toosendanin, respectively; 8c also displayed the most potent aphicidal activity against M. persicae with an LD50 value of 0.030 μg/larvae, which was closer to that of the commercial insecticidal etoxazole (0.026 μg/larvae); and 8s showed the best larvicidal activity against P. xylostella with an LC50 value of 0.27 mg/mL, which was 3.37-fold that of toosendanin and slightly higher than that of etoxazole (0.28 mg/mL). Furthermore, the control efficacy of 8s against P. xylostella in the pot experiments under greenhouse conditions was better than that of etoxazole. Structure-activity relationships (SARs) revealed that in most cases, the introduction of 1,3,4-oxadiazole/thiadiazole containing halophenyl groups at the C-13 position of (+)-nootkatone could obtain more active derivatives against M. separata, M. persicae, and P. xylostella than those containing other groups. In addition, toxicity assays indicated that these (+)-nootkatone derivatives had good selectivity to insects over nontarget organisms (normal mammalian NRK-52E cells and C. idella and N. denticulata fries) with relatively low toxicity. Therefore, the above results indicate that these (+)-nootkatone derivatives could be further explored as new lead compounds for the development of potential eco-friendly pesticides.

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.

Synthesis and biological evaluation of honokiol derivatives bearing 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3h)-ones as potential viral entry inhibitors against sars-cov-2

The 2019 coronavirus disease (COVID-19) caused by SARS-CoV-2 virus infection has posed a serious danger to global health and the economy. However, SARS-CoV-2 medications that are specific and effective are still being developed. Honokiol is a bioactive component from Magnoliae officinalis Cortex with damp-drying effect. To develop new potent antiviral molecules, a series of novel honokiol analogues were synthesized by introducing various 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones to its molecule. In a SARS-CoV-2 pseudovirus model, all honokiol derivatives were examined for their antiviral entry activities. As a result, 6a and 6p demonstrated antiviral entry effect with IC50 values of 29.23 and 9.82 μM, respectively. However, the parental honokiol had a very weak antiviral activity with an IC50 value more than 50 μM. A biolayer interfero-metry (BLI) binding assay and molecular docking study revealed that 6p binds to human ACE2 protein with higher binding affinity and lower binding energy than the parental honokiol. A competitive ELISA assay confirmed the inhibitory effect of 6p on SARS-CoV-2 spike RBD’s binding with ACE2. Importantly, 6a and 6p (TC50 > 100 μM) also had higher biological safety for host cells than honokiol (TC50 of 48.23 μM). This research may contribute to the discovery of potential viral entrance inhibitors for the SARS-CoV-2 virus, although 6p’s antiviral efficacy needs to be validated on SARS-CoV-2 viral strains in a biosafety level 3 facility.

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.