26459-51-8

Usage

Uses

Used in Optical Materials Industry:
(4-TERT-BUTYLPHENYL)BENZOATE is used as a component in the production of polycarbonate resins for optical materials. Its chemical structure contributes to the desired properties of the final product, such as transparency, durability, and resistance to impact.
Used in Chemical Synthesis:
(4-TERT-BUTYLPHENYL)BENZOATE is utilized in the preparation of aryl esters through a process involving acridinium-catalyzed photoredox C-O bond cleavage and acidolysis of diaryl ethers with aryl carboxylic acids. This method allows for the efficient synthesis of aryl esters, which are important intermediates in the production of various chemical compounds and pharmaceuticals.

Upstream product

• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 108-95-2 phenol 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 2751-90-8 tetraphenylphosphonium bromide 
• 98-80-6 phenylboronic acid 
• 64-18-6 formic acid 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 201230-82-2 carbon monoxide 
• 36600-66-5 4-tert-butylphenylhydrazine hydrochloride 
• 1710-98-1 p-tert-butyl benzoyl chloride 
• 50-00-0 formaldehyd 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 1864-94-4 phenyl formate 
• 637-87-6 1-Chloro-4-iodobenzene 

Downstream Products

• 4210-32-6 4-tert-butyl benzonitrile 
• 115933-42-1 tributyl(4-(tert-butyl)phenyl)stannane 
• 71209-71-7 p-tert-butylpropiophenone 
• 111564-56-8 1-(tert-butyl)-4-(3-(4-methoxyphenyl)propyl)benzene 
• 214360-66-4 2-(4-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Influence of substituents on the infrared stretching frequencies of carbonyl group in esters of benzoic acid

Infrared spectra of 25 substituted phenyl esters of benzoic acid C 6H5CO2C6H4-X (X=H, 3-Cl, 3-F, 3-CN, 3-NO2, 3-CH3, 3-OH, 3-NH2, 4-Cl, 4-F, 4-NO2, 4-CN, 4-

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.

Choline Hydroxide as a Versatile Medium for Catalyst-Free O-Functionalization of Phenols

A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal- and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.

An alternative route for boron phenoxide preparation from arylboronic acid and its application for C[sbnd]O bond formation

An efficient synthetic route to benzyl phenyl ether preparation has been successfully developed via a one-pot synthetic protocol utilizing a combination of arylboronic acids, hydrogen peroxide (H2O2), and benzyl halides. The whole procedure consists of two consecutive reactions, formation of boron phenoxide from arylboronic acids and its nucleophilic attack. A simple operation under mild conditions such as room-temperature ionic liquid (choline hydroxide), aerobic environment, and absence of metal- and base-catalysts has been employed. Expansion to utilize benzyl surrogates was also successfully accomplished.

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.

Nickel-Catalyzed Cross-Coupling of Aryl Redoxactive Esters with Aryl Zinc Reagents

A nickel-catalyzed aryl-aroyloxyl C(sp2)-O radical cross-coupling reaction conducted using a redox active ester with aryl zinc reagent was developed. This method demonstrates a new disconnection approach for formation of aryl aryl esters. In the one-pot sequential process, the readily available aryl carboxylic acids can be converted into functionalized aryl aryl esters and heteroaryl esters. This protocol is amenable to the gram-scale synthesis. The present method has a wide substrate scope and high functional group tolerance.

Rhodium-catalysed aryloxycarbonylation of iodo-aromatics by 4-substituted phenols with carbon monoxide or paraformaldehyde

Rhodium-catalysed phenoxycarbonylation of aryl iodides were carried out under carbon-monoxide atmosphere and in the absence of CO, using paraformaldehyde as an alternative surrogate for carbonylation reactions. Both strategies proved to be efficient for the synthesis of the corresponding phenyl esters. High pressure reactions provided the ester products with good selectivity, however lower activity was achieved compared to palladium containing systems. Using paraformaldehyde as carbon-monoxide source special reaction conditions are required, thus dramatic changes observed during optimisation reactions. Using in situ generated Rh-diphosphine catalyst systems, remarkable influence of ligand structure and solvent composition was observed on the activity and chemoselectivity. The substrate scope and the substituent effect were also investigated.

Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst

Readily available and inexpensive Earth-abundant alkali metal species are used as efficient catalysts for the transesterification of aryl or heteroaryl esters with phenols which is a challenging and underdeveloped transformation. The simple conditions and the use of heterogeneous alkali metal catalyst make this protocol very environmentally friendly and practical. This reaction fills in the missing part in transesterification reaction of phenols and provides an efficient approach to aryl esters, which are widely used in the synthetic and pharmaceutical industry.

Palladium-Catalyzed Oxidative Carbonylation of Aryl Hydrazines with CO and O2 at Atmospheric Pressure

Palladium-catalyzed aerobic oxidative aminocarbonylation and alkoxycarbonylation reactions with aryl hydrazines as coupling partners have been developed. The oxidative carbonylation of aryl hydrazines proceeded smoothly at atmospheric pressure CO, employi

Palladium-catalyzed alkoxycarbonylation of aryl halides with phenols employing formic acid as the CO source

An efficient palladium-catalyzed alkoxycarbonylation of aryl halides with phenols has been developed. Various aryl benzoates have been isolated in good to excellent yields with formic acid as the CO source. The reaction proceeds smoothly under mild conditions and good functional group tolerance was observed.