1871-38-1

Usage

Uses

Used in Pharmaceutical Industry:
Phenyl 4-chlorobenzoate is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and improving the efficacy of existing medications.
Used in Agricultural Chemical Industry:
Phenyl 4-chlorobenzoate is used as a starting material in the production of agricultural chemicals, such as pesticides and herbicides, to enhance crop protection and increase agricultural productivity.
Used in Dye and Pigment Synthesis:
Phenyl 4-chlorobenzoate is utilized as a starting material for the synthesis of dyes and pigments, providing a wide range of color options for various applications, including textiles, plastics, and printing inks.
Used in Fragrance and Flavor Formulation:
Phenyl 4-chlorobenzoate is used in the formulation of fragrances and flavors, adding unique scents and tastes to various consumer products, such as perfumes, cosmetics, and food items.
It is important to handle phenyl 4-chlorobenzoate with care, as it may pose health hazards if not properly managed.

InChI:InChI=1/C13H9ClO2/c14-11-8-6-10(7-9-11)13(15)16-12-4-2-1-3-5-12/h1-9H

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 108-95-2 phenol 
• 74-11-3 para-chlorobenzoic acid 
• 5216-25-1 4-chlorotrichloromethylbenzene 
• 17954-26-6 1,2-dihydro-2-phenoxycarbonylisoquinoline-1-carbonitrile 
• 6264-29-5 4-nitrophenyl 4-chlorobenzoate 
• 3229-70-7 phenolate 
• 102-09-0 bis(phenyl) carbonate 
• 637-87-6 1-Chloro-4-iodobenzene 
• 201230-82-2 carbon monoxide 
• 98-80-6 phenylboronic acid 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 104-88-1 4-chlorobenzaldehyde 
• 591-50-4 iodobenzene 

Downstream Products

• 79146-99-9 4-chloro-N-(thiazol-2-yl)benzamide 
• 37904-52-2 (4-chloro-benzoyl)-(4-nitro-benzenesulfonyl)-amine 
• 42019-78-3 4-chloro-4'-hydroxybenzophenone 
• 2985-79-7 4'-chloro-2-hydroxybenzophenone 
• 6282-15-1 4-chloro-benzoic acid-(3-nitro-anilide) 
• 61821-24-7 1,3-Bis-(4-chloro-phenyl)-2-methoxy-propane-1,3-dione 
• 49538-11-6 2-Benzenesulfonyl-1-(4-chloro-phenyl)-2-methoxy-ethanone 
• 41997-85-7 1-(4-Chloro-phenyl)-2-methoxy-2-(toluene-4-sulfonyl)-ethanone 
• 31401-26-0 N-(4-chlorobenzoyl)benzenesulfonamide 
• 555-24-8 lithium phenolate 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 78322-97-1 phenyl [1,1′-biphenyl]-4-carboxylate 
• 873-76-7 para-Chlorobenzyl alcohol 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Functional analysis of repositioned anilide derivatives as anticancer compounds

Off the different types cancers 40% of the population have been observed to be affected by leukemia. Contemporary therapeutics is focusing on generation of new synthetic analogues that can exert maximum positive physiological effect with minimum dosage and negligible deleterious side effects. New generation pharmacists are focusing on such promising effects of Imatinib (a potential anti-cancer drug molecule), Dasatinib, Pelitinib and Nilotinib. The present research study focuses on novel synthesized anilides derivative against BCR-ABL kinase as potential anti-leukemic agent. Validation of the compounds by molecular docking with specific BCR-ABL kinase confirmed their activity. Toxicity prediction of these compounds helped to identify sustainability as therapeutic molecules. The IC50 values were calculated (211 ug, 175 ug, 272ug for compounds A, B, C resp.) and the mode of cell death was gauged by DNA laddering assay. The cells were observed to be induced for programmed cell death. By validating and in-vivo testing of three synthesized compounds, the compound B was observed to be more stable thermodynamically with a potentially vital active site and appears to be a promising anti-leukemic factor. The present research thus lays a preliminary platform in world of pharmaceutics, where these new analogues appear to be efficient, target specific and less toxic molecules.

Conversion of esters to thioesters under mild conditions

We report conversion of esters to thioestersviaselective C-O bond cleavage/weak C-S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterification/decarbonylation and easy-to-handle gram scale thioesterification. Selectivity and computational studies were performed to gain insight into the formation of weak C-S bonds by C-O bond cleavage, which contrasts with the traditional trend of nucleophilic additions to carboxylic acid derivatives.

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

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.]

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.

Designing heterocyclic chalcones, benzoyl/sulfonyl hydrazones: An insight into their biological activities and molecular docking study

The aim of this study is to investigate the antioxidant, anticholinesterase and the antiproliferative activities of some chalcones, benzoyl and sulfonyl hydrazones. The antioxidant activity was studied by way of four complimentary assays and the anticholinesterase activity was studied using the Ellman method. The antiproliferative activity of the compounds was determined using a BrdU cell proliferation ELISA assay. Compound 32 (IC50: 15.58 ± 0.01 μg/mL) against the brain (C6) and 29 (IC50: 5.02 ± 0.05 μg/mL) against cervical (HeLa) cancer cell lines exhibited higher antiproliferative activity than the other compounds. Two sulfonyl hydrazone derivatives 45 and 47 exhibited very good antioxidant activity. The results of anticholinesterase activity indicated that nine compounds 3, 8, 10, 14, 24, 25, 27, 38, and 45 significantly inhibited acetylcholinesterase enzymes and thirty-three compounds 1–4, 7–14, 22–28, 32–41, 44–47 inhibited butyrylcholinesterase enzymes (BChE) more than galantamine. In addition, virtual screening methods based on ligand 45 having the best activity against BChE was used to define new human BChE inhibitors. The interactions of ligand 8 against acetylcholinesterase (AChE) were also examined. Important key residues were determined and visualized on completion of the methodology. All calculations indicated the suitability of use of the molecular docking approach for understanding interaction mechanisms and crucial fragments of novel hit compounds such as the potential lead AChE and BChE inhibitor candidates.

Studies of hydrogen isotope scrambling during the dehalogenation of aromatic chloro-compounds with deuterium gas over palladium catalysts

Catalytic dehalogenation of aromatic halides using isotopic hydrogen gas is an important strategy for labelling pharmaceuticals, biochemicals, environmental agents and so forth. To extend, improve and further understand this process, studies have been carried out on the scrambling of deuterium isotope with protium during the catalytic deuterodehalogenation of model aryl chlorides using deuterium gas and a palladium on carbon catalyst in tetrahydrofuran solution. The degree of scrambling was greatest with electron-rich chloroarene rings. The tetrahydrofuran solvent and the triethylamine base were not the source of the undesired protium; instead, it arose, substantially, from the water content of the catalyst, though other sources of protium may also be present on the catalyst. Replacement of the Pd/C catalyst with one prepared in situ by reduction of palladium trifluoroacetate with deuterium gas and dispersed upon micronised polytetrafluoroethylene led to much reduced scrambling (typically 0–6% compared with up to 40% for palladium on carbon) and to high atom% abundance, regiospecific labelling. The improved catalytic system now enables efficient polydeuteration via the dehalogenation of polyhalogenated precursors, making the procedure viable for the preparation of MS internal standards and, potentially, for high specific activity tritium labelling.

Design and Bioevaluation of Novel Hydrazide-Hydrazones Derived from 4-Acetyl-N-Substituted Benzenesulfonamide

Abstract: In this research, a series of hydrazine-hydrazone derivatives (Ia–g), (IIa–h) were synthesized to discover new antioxidant and anticholinesterase agents. The structures of synthesized compounds were characterized by spectroscopic data using UV, IR, 1H, 13C NMR, mass spectroscopy, and elemental analysis. The bio-evaluation of the synthesized compounds (Ia–g), (IIa–h) were evaluated according to in vitro activity assays. The results of β-carotene/linoleic acid assay showed that among the synthesized compounds, the (Ib), (Ie), (IIb–IIe), and (IIh) compound exhibited higher activity for the lipid peroxidation inhibitory activity. In the DPPH free scavenging activity and the cation radical scavenging activity in ABTS?+ activity, compound (IIb) was found to be more active. In the CUPRAC reduced power assay, the A0.5 values of all synthesized compounds were better than α-TOC. In AChE assay, compound (IIb) exhibited the most activity with IC50 = 11.12 ± 0.74 μM, while the compounds (Ib–g) and (IIb–h), exhibited excellent activity than the positive standard galantamine (IC50 = 46.06 ± 0.10 μM) in the BChE assay.

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.