5398-17-4

Usage

Uses

Used in Pharmaceutical and Bioactive Molecule Synthesis:
2-(4-methoxybenzyl)benzoic acid is used as a building block for the synthesis of various pharmaceuticals and bioactive molecules, contributing to the development of new drugs and therapeutic agents.
Used in Anti-inflammatory and Anti-cancer Research:
2-(4-methoxybenzyl)benzoic acid is used as a compound with potential anti-inflammatory and anti-cancer properties, being studied for its effects on reducing inflammation and inhibiting cancer cell growth.
Used in Dye and Fragrance Production:
2-(4-methoxybenzyl)benzoic acid is used as a precursor in the production of dyes and fragrances, providing a foundation for the creation of various colorants and aromatic compounds.
Used in Material and Polymer Development:
2-(4-methoxybenzyl)benzoic acid is used in the development of new materials and polymers, leveraging its unique chemical structure to enhance material properties and performance.

Upstream product

• 85-44-9 phthalic anhydride 
• 85-57-4 2-(4-hydroxy-benzoyl)-benzoic acid 
• 124-38-9 carbon dioxide 
• 68355-78-2 1-bromo-2-(4-methoxybenzyl)benzene 
• 59142-64-2 2-bromo-α-(4-methoxyphenyl)benzyl alcohol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1151-15-1 2-(4-methoxybenzoyl)benzoic acid 
• 7758-99-8 copper(II) sulfate 
• 7440-66-6 zinc 
• 100-66-3 methoxybenzene 
• 108-95-2 phenol 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 7664-41-7 ammonia 

Downstream Products

• 500282-70-2 2-(4-methoxy-benzyl)-benzoic acid ethyl ester 
• 53604-95-8 2-methoxy-9(10H)-anthracenone 
• 1456693-98-3 3-hydroxy-2-methoxy-3-(4-methoxyphenyl)isoindolin-1-one 
• 21615-74-7 3-(4-methoxyphenyl)phthalide 
• 10324-42-2 2-(4-Methoxybenzyl) benzylchlorid 
• 1026396-79-1 5-(4-Methoxy-benzyl)-4H-isoquinoline-3,3-dicarboxylic acid diethyl ester 
• 1028289-57-7 2-Formylamino-2-[2-(4-methoxy-benzyl)-benzyl]-malonic acid diethyl ester 
• 1026228-02-3 5-(4-Methoxy-benzyl)-1,4-dihydro-2H-isoquinoline-3,3-dicarboxylic acid diethyl ester 
• 1026413-47-7 Methanesulfonic acid 2-(4-methoxy-benzyl)-benzyl ester 
• 69007-91-6 C₁₅H₁₅BrO 
• 10324-41-1 2-(4-Methoxybenzyl)-phenyl-acetonitril 
• 10324-03-5 (4-Methoxybenzyl)-2-phenylessigsaeure 
• 10324-43-3 2-<(4-methoxyphenyl)methyl>benzyl alcohol 
• 10324-44-4 methyl 2-<(4-methoxyphenyl)methyl>benzoate 

Relevant academic research and scientific papers

Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones

A copper-catalyzed aerobic 3-hydroxyisoindolinone synthesis was developed via the benzylic double C(sp3)-H functionalization of 2-alkylbenzamides. In this reaction, molecular oxygen was used as both an oxidant for C(sp3)-H functionalization and an oxygen source. Our method can be extended to diverse benzylic C(sp3)-H bonds and shows excellent functional group tolerance. This journal is

Completing the Redox-Series of Silicon Trisdioxolene: ortho-Quinone and Lewis Superacid Make a Powerful Redox Catalyst

Quinones are mild oxidants, the redox potentials of which can be increased by supramolecular interactions. Whereas this goal has been achieved by hydrogen bonding or molecular encapsulation, a Lewis acid-binding strategy for redox amplification of quinones is unexplored. Herein, the redox chemistry of silicon tris(perchloro)dioxolene 1 was studied, which is the formal adduct of ortho-perchloroquinone QCl with the Lewis superacid bis(perchlorocatecholato)silane 2. By isolating the anionic monoradical 1.?, the redox-series of a century-old class of compounds was completed. Cyclic voltammetry measurements revealed that the redox potential in 1 was shifted by more than 1 V into the anodic direction compared to QCl, reaching that of “magic blue” or NO+. It allowed oxidation of challenging substrates such as aromatic hydrocarbons and could be applied as an efficient redox catalyst. Remarkably, this powerful reagent formed in situ by combining the two commercially available precursors SiI4 and QCl.

A Novel Three-Step Tandem Reaction for Efficient Syntheses of Bulky Anthracenyl Esters from 2-Benzylbenzoic Acids

Bulky anthracenyl esters could be efficiently synthesized from 2-benzylbenzoic acids via a novel three-step tandem reaction containing intramolecular Friedel-Crafts acylation, enolization, and esterification. A mechanism for the tandem reaction is proposed.

Activation of Electron-Deficient Quinones through Hydrogen-Bond-Donor-Coupled Electron Transfer

Quinones are important organic oxidants in a variety of synthetic and biological contexts, and they are susceptible to activation towards electron transfer through hydrogen bonding. Whereas this effect of hydrogen bond donors (HBDs) has been observed for Lewis basic, weakly oxidizing quinones, comparable activation is not readily achieved when more reactive and synthetically useful electron-deficient quinones are used. We have successfully employed HBD-coupled electron transfer as a strategy to activate electron-deficient quinones. A systematic investigation of HBDs has led to the discovery that certain dicationic HBDs have an exceptionally large effect on the rate and thermodynamics of electron transfer. We further demonstrate that these HBDs can be used as catalysts in a quinone-mediated model synthetic transformation.

C-ARYL GLYCOSIDE COMPOUNDS FOR THE TREATMENT OF DIABETES AND OBESITY

This invention relates to a compound of generic formula (I): (I) as well as a pharmaceutically acceptable salt thereof, a tautomer, optical isomer or a mixture of optical isomers in any proportion, in particular a mixture of enantiomers, and particularly a racemate mixture, in particular for use thereof as a drug, notably in the treatment of diabetes.

Efficient synthesis of isobenzofuran-1(3H)-ones (Phthalides) and selected biological evaluations

The studies presented here deal with the convenient and efficient one-step conversion of o-alkylbenzoic acids into their corresponding isobenzofuran-1 (3H)-ones (phthalides) using NaBrO3/NaHSO3 in a two-phase system. A range of o-alkylbenzoic acids was used with the object of getting a variety of phthalide derivatives as multipurpose biologically active compounds. Seventeen phthalides have been synthesized and tested for cytotoxicity, antibacterial and antifungal activities. Some of these compounds showed promising cytotoxic effects against Artemia salina. Compounds 4j-4p were highly active against Gram-negative and Gram-positive bacteria among all tested compounds. In the fungicidal assay, the compounds showed a broad spectrum of activity against six fungi. All compounds were characterized via elemental analysis, UV, IR, mass and-NMR spectroscopy. ECV · Editio Cantor Verlag.

Tricyclic alkylamides as melatonin receptor ligands with antagonist or inverse agonist activity

This work reports the design and synthesis of novel alkylamides, characterized by a dibenzo[a,d] cycloheptene nucleus, as melatonin (MLT) receptor ligands. The tricyclic scaffold was chosen on the basis of previous quantitative structure-activity studies on MT1 and MT2 antagonists, relating selective MT2 antagonism to the presence of an aromatic substituent out of the plane of the MLT indole ring. Some dibenzo seven-membered structures were thus selected because of the noncoplanar arrangement of their benzene rings, and an alkylamide chain was introduced to fit the requirements for MLT receptor binding, namely, dibenzocycloheptenes with an acylaminoalkyl side chain at position 10 and dibenzoazepines with this side chain originating from the nitrogen atom bridging the two phenyl rings. Binding affinity at human cloned MT1 and MT2 receptors was measured by 2[125I] iodomelatonin displacement assay and intrinsic activity by the GTPγS test. The majority of the compounds were characterized by higher affinity at the MT2 than at the MT 1 receptor and by very low intrinsic activity values, thus confirming the importance of the noncoplanar arrangement of the two aromatic rings for selective MT2 antagonism. Dibenzocycloheptenes generally displayed higher MT1 and MT2 affinity than dibenzoazepines. N-(8-Methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ylmethyl)propionamide (4c) and -butyramide (4d) were the most selective MT2 receptor antagonists of the series, with MT2 receptor affinity comparable to that of melatonin and as such among the highest reported in the literature for MLT receptor antagonists. The acetamide derivative 4b produced a noticeable reduction of GTPγS binding at MT2 receptor, thus being among the few inverse agonists described.

Direct synthesis of γ-substituted phthalides by cyclization of benzyl radicals generated from o-(arylmethyl)benzoic acids

Direct oxidation of o-(arylmethyl)benzoic acids with sodium peroxysulfate-copper(II) chloride in water yields γ-substituted phthalides. The reaction is highly regioselective, and the corresponding γ-butyro-lactones are the only products formed through intermediate stable arylmethyl radicals.

Direct Synthesis of γ-Substituted Phthalides Via ortho-Aryl Benzoic Acid Mediated Benzyl Radical Cyclization

Direct synthesis of γ-substituted phthalids from related ortho-aryl benzoic acids with 48-85% yield are covered. The direct oxidation in the presence of peroxydisulphate-copper (II) chloride in aqueous medium was applied. The reaction is highly regioselective and leads exclusively to γ-butyrolactone, through very stable benzylic radical intermediate.

An alternative method for the synthesis of γ-lactones by using cesium fluoride-celite/acetonitrile combination

A variety of 2-(1-bromoalkyl) benzoic acids 4 undergo intramolecular nucleophilic substitution reaction when treated with a CsF-Celite as solid base in acetonitrile under reflux condition to give the corresponding cyclized phthalides in moderate to very good yield. These 2-(1-bromoalkyl) benzoic acids 4 are formed by the α-bromination of 2-alkylbenzoic acids 3 using N-bromosuccinimide and a catalytic amount of α,α′ -azoisobutyronitrile in carbon tetrachloride under reflux.