4181-97-9

Usage

Uses

Used in Pharmaceutical Industry:
4-METHOXY-BENZOIC ACID PHENYL ESTER is used as a reagent for the synthesis of pyrazoles via iodine catalyzed denitrative imino-diaza-Nazarov cyclization. This application is significant in the development of new pharmaceutical compounds, as pyrazoles are known to possess diverse biological activities, including anti-inflammatory, antifungal, and anticancer properties.
Used in Enzyme Inhibition:
In the field of biochemistry and molecular biology, 4-METHOXY-BENZOIC ACID PHENYL ESTER is used as a potent inhibitor of 15-lipoxygenase, an enzyme involved in the metabolism of fatty acids and the production of inflammatory mediators. By inhibiting this enzyme, the compound may contribute to the development of treatments for various inflammatory diseases and conditions.

InChI:InChI=1/C14H12O3/c1-16-12-9-7-11(8-10-12)14(15)17-13-5-3-2-4-6-13/h2-10H,1H3

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 108-95-2 phenol 
• 100-09-4 4-methoxybenzoic acid 
• 17954-26-6 1,2-dihydro-2-phenoxycarbonylisoquinoline-1-carbonitrile 
• 106-41-2 4-bromo-phenol 
• 201230-82-2 carbon monoxide 
• 733-53-9 p-methoxyphenyl(phenyl)iodonium tetrafluoroborate 
• 102-09-0 bis(phenyl) carbonate 
• 696-62-8 para-iodoanisole 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 13360-92-4 phenyl diphenylphosphinite 
• 164594-13-2 Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 98-80-6 phenylboronic acid 

Downstream Products

• 611-99-4 4,4'-Dihydroxybenzophenone 
• 61002-54-8 4-hydroxy-4'-methoxybenzophenone 
• 27410-09-9 3-(p-Anisyl)-1,4-pentadiin-3-ol 
• 87228-56-6 1-(4-Methoxy-phenyl)-2-methylsulfanyl-2-(toluene-4-sulfonyl)-ethanone 
• 3229-70-7 phenolate 
• 16285-97-5 p-methoxybenzoate^(1-) 
• 138630-68-9 3,4-Dihydro-6-methoxy-1-(4-methoxybenzoyl)-2(1H)-naphthalenone 
• 61821-26-9 2-Methoxy-1,3-bis-(4-methoxy-phenyl)-propane-1,3-dione 
• 21160-15-6 Phenyl-<α-(4-methoxy-benzoyl)-α-methoxy-methyl>-sulfon 
• 21160-14-5 p-Tolyl-<α-(4-methoxy-benzoyl)-α-methoxymethyl>-sulfon 
• 63619-82-9 3-(4-methoxyphenyl)-4-(4-methoxybenzoyl)-1,2-dihydronaphthalene 
• 63084-03-7 6-methoxy-2-[(4-methoxyphenyl)carbonyl]-2,3,4-trihydronaphthalen-1-one 
• 63119-40-4 1-oxo-2-(4-methoxybenzoyl)-5-methoxyindane 
• 121-98-2 methyl 4-methoxybenzoate 

Relevant academic research and scientific papers

Transesterification kinetics investigation of r-substituted phenyl benzoates with 4-methoxyphenol in the presence of K2CO3 in DMF

Transesterification of R-substituted phenyl benzoates 1-5 with 4-methoxyphenol 6 was kinetically investigated in the presence of K 2CO3 in dimethylformamide (DMF) at various temperatures. The Hammett plots for the reactions of the 1-

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

Palladium Catalyzed Regioselective Cyclization of Arylcarboxylic Acids via Radical Intermediates with Diaryliodonium Salts

Palladium-catalyzed C2-arylation/intramolecular acylation with arylcarboxylic acids was developed by using diaryliodonium salts. The protocol has the advantage of good step-economy by two chemical bonds formation in one pot.

Transition-Metal-Free DMAP-Mediated Aromatic Esterification of Amides with Organoboronic Acids

A new, transition-metal-free, effective method for aromatic esterification of amides with organoboronic acids has been developed. A wide range of benzoate derivatives were obtained with yields ranging from moderate to good. The catalytic reaction shows a broad substrate scope and excellent functional group tolerance. Conceptually, DMAP mediates the reaction and is crucial for this transformation.

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Palladium-catalyzed aryloxy- and alkoxycarbonylation of aromatic iodides in γ-valerolactone as bio-based solvent

Fossil-based solvents and triethylamine as a toxic and volatile base were successfully replaced with γ-valerolactone as a non-volatile solvent and K2CO3 as inorganic base in the alkoxy- and aryloxycarbonylation of aryl iodides using phosphine-free Pd catalyst systems. By this, the traditional systems were not simply replaced but also significantly improved. In the study, the effects of different reaction parameters, i.e. the use of several other solvents, the temperature, the carbon monoxide pressure, the base and the catalyst concentrations, were evaluated in details on the efficiency of the carbonylations. To gather some information on the mechanism of these reactions, the effects of the electronic parameters (σ) of various aromatic substituents of the aryl iodides as well as the influence of para-substitution of phenol were investigated on the activity. For a comparison, the aryl-substituted aryl iodides were also reacted with methanol and aryl iodide was also alkoxycarbonylated using several different lower alcohols. From the observed correlations between the electronic parameters of the aromatic substituents and the rates, it appears that the rate determining step is the oxidative addition of Ar–I to Pd0, provided that sufficient amounts of nucleophiles are present for the ester formation. If this is not the case, the rate of nucleophile attack might determine the overall rate.

Ester Transfer Reaction of Aromatic Esters with Haloarenes and Arenols by a Nickel Catalyst

A catalytic ester transfer reaction of aromatic esters with aryl halides/arenols was developed. The present reaction can transfer an ester functional group from certain aromatic esters to haloarenes. This ester transfer reaction involves two oxidative additions-one from the C-C bond of the aromatic ester and one from the C-halogen bond of haloarenes-onto a nickel catalyst. The utilization of a Ni/dcypt catalyst capable of cleaving both chemical bonds was a key for the reaction progress. Furthermore, naphthol-based aryl electrophiles were also applicable to the catalytic system via C-O bond activation.

Palladium-catalyzed carbonylative transformation of phenols via in-situ triflyl exchangement

Phenols are attractive starting materials due to their ready availability. Herein, we developed a novel method on palladium-catalyzed alkoxycarbonylation of phenols. By using commercially available Pd(OAc)2 and PtBu3·HBF4 as the catalyst system and aryl triflates as triflyl source to activate the other phenol, various carboxylic acid esters were prepared in moderate to good yields via Tf exchange and then O-Tf bond cleavage. Notably, phenols generated from aryl triflates after Tf transfer or other additional aliphatic alcohols can all be employed as nucleophiles to synthesize the corresponding esters.

Ligand-Controlled C?O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

Palladium-catalyzed cross-coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C?C bond coupling and C?H arylation are well established in the literature. However, direct C?O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C?O bond formation, enabled by a bidentate N,N-ligand such as 1,10-phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon-carbon bond coupling. (Figure presented.).

Supramolecular Pd(II) complex of DPPF and dithiolate: An efficient catalyst for amino and phenoxycarbonylation using Co2(CO)8 as sustainable C1 source

Highly active, efficient and robust “dppf ligated tetranuclear palladium dithiolate complex” was synthesized and applied as a catalyst for chemical fixation of carbon monoxide for the synthesis value added chemicals such as tertiary amide and aromatic esters. The synthesized catalyst was characterized using different analytical techniques such as elemental analysis, 1H and 31P NMR spectroscopy. The use of Co2(CO)8 as a cheap, less toxic and low melting solid surrogate are additional advantages over the current protocol. The catalyst showed superior activity towards the Amino (10?3 mol % catalyst) and Phenoxycarbonylation (10-2 mol % catalyst) and high TON (104 to 103) and TOF (103 to 102 h-1). The Betol and Lintrin (active drug molecules) were synthesized under an optimized reaction condition. The scalability of the current protocol has been demonstrated up-to the gram level.