41806-25-1

Usage

Uses

Used in Chemical Synthesis:
1-(4-CHLOROPHENYL)-2-PHENOXY-1-ETHANONE is used as a reagent for the synthesis of styrenyl ethers. It plays a crucial role in the Bamford-Stevens reaction of aryloxy/alkoxy acetophenones, which is a widely employed method for the preparation of styrene derivatives. These derivatives find applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(4-CHLOROPHENYL)-2-PHENOXY-1-ETHANONE serves as an intermediate in the synthesis of various drug molecules. Its unique structural features allow for the development of new compounds with potential therapeutic applications.
Used in Agrochemical Industry:
1-(4-CHLOROPHENYL)-2-PHENOXY-1-ETHANONE is also utilized in the agrochemical industry for the synthesis of novel compounds with pesticidal, herbicidal, or fungicidal properties. Its structural versatility enables the development of new molecules with improved efficacy and selectivity.
Used in Materials Science:
In the field of materials science, 1-(4-CHLOROPHENYL)-2-PHENOXY-1-ETHANONE can be employed in the development of advanced materials, such as polymers and composites, with tailored properties for specific applications. Its reactivity and structural features make it a valuable building block for the design of new materials with enhanced performance characteristics.

Upstream product

• 99-91-2 para-chloroacetophenone 
• 104-88-1 4-chlorobenzaldehyde 
• 111198-02-8 1-(phenoxymethyl)-1H-benzo[d][1,2,3]triazole 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 108-95-2 phenol 

Downstream Products

• 99-91-2 para-chloroacetophenone 
• 41907-02-2 α-bromo-4-chloro-α-phenoxyacetophenone 
• 29509-28-2 1-(4-chlorophenyl)-2-phenoxyethanol 
• 1304788-11-1 (S)-1-(4-chlorophenyl)-2-phenoxyethanol 

Relevant academic research and scientific papers

Synthesis and in vitro anti-Toxoplasma gondii activity of a new series of aryloxyacetophenone thiosemicarbazones

Abstract: A new series of aryloxyacetophenone thiosemicarbazones 4a–q have been synthesized as anti-Toxoplasma gondii agents. All compounds showed significant inhibitory activity against T. gondii-infected cells (IC50 values 1.09–25.19?μg/mL). The 4-fluorophenoxy derivative (4l) was the most potent compound with the highest selectivity toward host cells (SI = 19), being better than standard drug pyrimethamine. SAR study indicated that the concurrence of proper substituents on both aryl ring of phenoxyacetophenone is important for potency and safety profile. Further in vitro experiments with the representative compounds 4l and 4p revealed that these compounds at the concentration of 5?μg/mL can significantly reduce the viability of T. gondii tachyzoites, as well as their infectivity rate and intracellular proliferation, comparable to those of pyrimethamine. Graphic abstract: [Figure not available: see fulltext.]

Cobalt-Catalyzed Reductive C-O Bond Cleavage of Lignin β-O-4 Ketone Models via in Situ Generation of the Cobalt-Boryl Species

An efficient and mild method for reductive C-O bond cleavage of lignin β-O-4 ketone models was developed to afford the corresponding ketones and phenols with PDI-CoCl2 as the precatalyst and diboron reagent as the reductant. The synthetic utility of the methodology was demonstrated by depolymerization of a polymeric model and gram-scale transformation. Mechanistic studies suggested that this transformation involves steps of carbonyl insertion, 1,2-Brook type rearrangement, β-oxygen elimination, and rate-limiting regeneration of the catalytic active Co-B species.

Structural design, synthesis and structure-activity relationships of thiazolidinones with enhanced anti-Trypanosoma cruzi activity

Pharmacological treatment of Chagas disease is based on benznidazole, which displays poor efficacy when administered during the chronic phase of infection. Therefore, the development of new therapeutic options is needed. This study reports on the structural design and synthesis of a new class of anti-Trypanosoma cruzi thiazolidinones (4 a-p). (2-[2-Phenoxy-1-(4-bromophenyl) ethylidene)hydrazono]-5-ethylthiazolidin-4-one (4 h) and (2-[2-phenoxy-1-(4- phenylphenyl)ethylidene)hydrazono]-5-ethylthiazolidin-4-one (4 l) were the most potent compounds, resulting in reduced epimastigote proliferation and were toxic for trypomastigotes at concentrations below 10 μM, while they did not display host cell toxicity up to 200 μM. Thiazolidinone 4 h was able to reduce the in vitro parasite burden and the blood parasitemia in mice with similar potency to benznidazole. More importantly, T. cruzi infection reduction was achieved without exhibiting mouse toxicity. Regarding the molecular mechanism of action, these thiazolidinones did not inhibit cruzain activity, which is the major trypanosomal protease. However, investigating the cellular mechanism of action, thiazolidinones altered Golgi complex and endoplasmic reticulum (ER) morphology, produced atypical cytosolic vacuoles, as well as induced necrotic parasite death. This structural design employed for the new anti-T. cruzi thiazolidinones (4 a-p) led to the identification of compounds with enhanced potency and selectivity compared to first-generation thiazolidinones. These compounds did not inhibit cruzain activity, but exhibited strong antiparasitic activity by acting as parasiticidal agents and inducing a necrotic parasite cell death. Stop the cycle! The attachment of an aryl ring to the iminic carbon produced thiazolidinones that are conformationally more restricted than first-generation thiazolidinones. This enhanced the potency of antiparasitic thiazolidinones, as observed under treatment with compound 4 h where parasite development and invasion in host cells were substantially reduced. Copyright

Liquid chromatographic resolution of mexiletine and its analogs on crown ether-based chiral stationary phases

Mexiletine, an effective class IB antiarrhythmic agent, and its analogs were resolved on three different crown ether-based chiral stationary phases (CSPs), one (CSP 1) of which is based on (+)-(18-crown-6)-2,3,11,12- tetracarboxylic acid and the other two (CSP 2 and CSP 3) are based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6. Mexiletine was resolved with a resolution (RS) of greater than 1.00 on CSP 1 and CSP 3 containing residual silanol group-protecting n-octyl groups on the silica surface, but with a resolution (RS) of less than 1.00 on CSP 2. The chromatographic behaviors for the resolution of mexiletine analogs containing a substituted phenyl group at the chiral center on the three CSPs were quite dependent on the phenoxy group of analytes. Namely, mexiletine analogs containing 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3-methylphenoxy, 4-methylphenoxy, and a simple phenoxy group were resolved very well on the three CSPs even though the chiral recognition efficiencies vary with the CSPs. However, mexiletine analogs containing 2-methylphenoxy group were not resolved at all or only slightly resolved. Among the three CSPs, CSP 3 was found to show the highest chiral recognition efficiencies for the resolution of mexiletine and its analogs, especially in terms of resolution (RS). Chirality 26:272-278, 2014. 2014 Wiley Periodicals, Inc.

Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: Application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols

An enantioselective borane-mediated reduction of a variety of 2-haloketones with 10% spiroaminoborate ester 1 as catalyst is described. By a simple basic workup of 2-halohydrins, optically active epoxides are obtained in high yield and with excellent enantiopurity (up to 99% ee). Ring-opening of oxiranes with phenoxides or sodium azide is investigated under different reaction conditions affording nonracemic 1,2-hydroxy ethers and 1,2-azido alcohols with excellent enantioselectivity (99% ee) and in good to high chemical yield. 2011 American Chemical Society.

Transformation of aryl acyloin O-alkyl and O-phenyl derivatives to ketones

The treatment of aryl acyloin (α-hydroxyketone) O-alkyl and O-phenyl derivatives with 2-3 equiv of Zn and 1-2 equiv of NH4Cl in ethanol, refluxing for 20-120 min, gave the corresponding ketones with excellent yields. Further, α,β-epoxy ketones can be efficiently transformed to β-hydroxy ketones, and 2,2-dialkoxy-1-phenyl ketone also can be dealkoxylated to 1-phenyl ketone. Copyright Taylor & Francis Group, LLC.

Base-catalyzed rearrangement of α-benzotriazolyl alkoxide anions: Synthesis of one-carbon homologated α-substituted alkyl ketones

Deprotonated benzotriazole derivatives (1a-c) reacted with aldehydes to give the α-oxyanion substituted intermediates (2), which upon further treatment with butyllithium, without separation, resulted in the formation of one-carbon homologated α-substituted alkyl ketones (6a-f). Similar treatment of benzotriazole derivatives (1d-f) generated the benzotriazole ring-opening and rearranged products (7a-f). Plausible mechanisms for these reactions have been proposed.

N-aryl-3-aryl-4-substituted-4,5-dihydro-1H-pyrazole-1-carboxamides and methods of their production

This invention relates to novel N-aryl-3-aryl-4-substituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.

Palladium (0) catalyzed nucleophilic substitution on 2-cyclopropylidene-phenoxy ethanes

2-cyclopropylidene-phenoxy ethanes 5, 2-substituted with alkyl, aryl or heterocyclic groups are readily obtained in high yields by the Wittig reaction of the easily accessible α-phenoxy etanones 4 with (3-bromo propyl) triphenylphosphonium bromide. They react with complete regioselectivity in palladium (0) catalyzed nucleophilic substitutions with a series of soft carbon nucleophiles giving an easy entry to 5,6-methanoamino acids.

Azide and isocyanate derivatives of 2-nitro-3-phenylbenzofuran

2-Nitro-3-phenylbenzofurans wherein the benzo or 3-phenyl portion of the molecule is bonded directly to an azide or an isocyanate group.