1900-85-2

Usage

Uses

Used in Fragrance Industry:
Phenyl 4-methylbenzoate is used as a flavoring agent and fragrance ingredient for its sweet, floral scent, enhancing the aroma of consumer products such as perfumes, lotions, and soaps.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, phenyl 4-methylbenzoate is utilized in the manufacturing process, contributing to the development of medicinal products, likely due to its chemical properties that can be manipulated in synthesis reactions.
Used in Organic Synthesis:
Phenyl 4-methylbenzoate is also employed in organic synthesis reactions, where its chemical structure is key to creating other compounds or products, taking advantage of its reactivity and functional groups in chemical processes.

Upstream product

• 99-94-5 p-Toluic acid 
• 108-95-2 phenol 
• 13222-85-0 p-methylbenzoic anhydride 
• 139-02-6 sodium phenoxide 
• 153921-22-3 Se-diphenylarsanyl 4-methylbenzenecarboselenoate 
• 17954-26-6 1,2-dihydro-2-phenoxycarbonylisoquinoline-1-carbonitrile 
• 874-60-2 4-methyl-benzoyl chloride 
• 100-66-3 methoxybenzene 
• 106-41-2 4-bromo-phenol 
• 15023-67-3 4-nitrophenyl 4-methylbenzoate 
• 3229-70-7 phenolate 
• 102-09-0 bis(phenyl) carbonate 
• 106-43-4 para-chlorotoluene 
• 71-43-2 benzene 

Downstream Products

• 150175-93-2 4-methyl-N-(thiazol-2-yl)benzamide 
• 6833-18-7 4-methyl-N-phenylbenzamide 
• 92967-43-6 (N-acetyl-sulfanilyl)-p-toluoyl-amine 
• 27410-07-7 3--3-aethinyl-3-hydroxy-propin-(1) 
• 87228-57-7 2-Methylsulfanyl-2-(toluene-4-sulfonyl)-1-p-tolyl-ethanone 
• 35092-35-4 4-Bromomethyl benzoic acid phenyl ester 
• 134-92-9 4-hydroxy-4'-methylbenzophenone 
• 19434-30-1 2-hydroxy-4'-methylbenzophenone 
• 3229-70-7 phenolate 
• 5118-31-0 4-methylbenzoate 
• 41997-73-3 2-Benzenesulfonyl-2-methoxy-1-p-tolyl-ethanone 
• 41997-82-4 2-Methoxy-2-(toluene-4-sulfonyl)-1-p-tolyl-ethanone 
• 28137-36-2 (2-methoxyphenyl)(4-methylphenyl)methanone 
• 104-87-0 4-methyl-benzaldehyde 

Relevant academic research and scientific papers

Mechanically induced solvent-free esterification method at room temperature

Herein, we describe two novel strategies for the synthesis of esters, as achieved under high-speed ball-milling (HSBM) conditions at room temperature. In the presence of I2 and KH2PO2, the reactions afford the desired esterification derivatives in 45% to 91% yields within 20 min of grinding. Meanwhile, using KI and P(OEt)3, esterification products can be obtained in 24% to 85% yields after 60 min of grinding. In addition, the I2/KH2PO2 protocol was successfully extended to the late-stage diversification of natural products showing the robustness of this useful approach. Further application of this method in the synthesis of inositol nicotinate was also discussed. This journal is

Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.

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.

Method for preparing diaryl ester compound through efficient catalysis of pyridine palladium

The invention discloses a method for preparing a diaryl ester compound through efficient catalysis of pyridine palladium. The method is used for high-efficiency high-yield preparation of the diaryl ester compound under mild conditions by taking a phenol compound, an iodobenzene compound and carbon monoxide as raw materials, triethylamine as alkali and pyridine palladium as a catalyst. The method provided by the invention has the advantages of less usage amount of the palladium catalyst, high catalytic activity of the palladium catalyst, stability of the palladium catalyst to air, simple operation, short reaction time and high atom economy, opens up a low-cost, green and efficient way for preparation of diaryl ester compounds, and has broad application prospects.

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.

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.

Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols

In this report, we have developed a sustainable protocol for the synthesis of aromatic esters by a carbonylative method using di-μ-chlorobis [5-hydroxy-2-[1-(hydroxyimino-?N) ethyl] phenyl-?C] palladium (II) dimer (1) catalyst in PEG-400 as a greener and recyclable solvent. The reaction is carried out at room temperature using CO in a balloon. Good to excellent yield of various esters can be synthesize using this protocol. Direct insertion of CO moiety leads to the high atom and step economy. Compared to previous protocol this phosphine free approach for the synthesis of aromatic esters provides high Turnover Number (TON) and Turnover Frequency (TOF). Developed approach has an alternative route for use of conventional palladium precursor with high conversion and selectivity. The catalyst system and product can easily be separated using diethyl ether as a solvent. The Pd/PEG-400 system could be reused up to a fifth consecutive cycle without any loss of its activity and selectivity.

PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis

By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.