62482-45-5

Usage

Uses

Used in Pharmaceutical Industry:
3'-Chloro-2-phenylacetophenone is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 3'-chloro-2-phenylacetophenone serves as a valuable building block for the creation of a wide range of organic compounds. Its reactivity and functional groups enable chemists to synthesize complex molecules for various applications.

InChI:InChI=1/C14H11ClO/c15-13-8-4-7-12(10-13)14(16)9-11-5-2-1-3-6-11/h1-8,10H,9H2

Upstream product

• 618-48-4 3-chlorobenzamide 
• 6921-34-2 benzylmagnesium chloride 
• 766-84-7 3-chloro-benzonitrile 
• 72867-64-2 N-[1-(3-Chloro-phenyl)-1-cyano-2-phenyl-ethyl]-N-phenyl-benzamide 
• 72867-29-9 2-(3-chlorophenyl)-2-(phenylamino) acetonitrile 
• 587-04-2 m-Chlorobenzaldehyde 
• 100-39-0 benzyl bromide 
• 4039-32-1 lithium hexamethyldisilazane 
• 33756-91-1 tris(3-chlorophenyl)bismuthane 
• 103-80-0 phenylacetyl chloride 
• 63503-60-6 3-chlorophenylboronic acid 
• 140-29-4 phenylacetonitrile 
• 201230-82-2 carbon monoxide 
• 100-44-7 benzyl chloride 

Downstream Products

• 181697-29-0 1-(3-chlorophenyl)-2-phenyl-ethan-1-one oxime 
• 7498-72-8 1-(3-chlorophenyl)-2-phenylethane-1,2-dione 
• 1384131-20-7 (Z)-1-t-butyldimethylsilyloxy-1-(3-chlorophenyl)-2-phenylethene 
• 181696-19-5 4-[3-(3-chlorophenyl)-5-methylisoxazol-4-yl]benzenesulfonamide 
• 1283117-46-3 6-(3-chlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one 

Relevant academic research and scientific papers

Visible-Light-Promoted [3 + 2] Cycloaddition of 2H-Azirines with Quinones: Access to Substituted Benzo[f]isoindole-4,9-diones

A visible-light-promoteded [3 + 2] cycloaddition reaction of 2H-azirines with quinones has been developed under mild reaction conditions. The reaction provides a general and efficient strategy for the synthesis of the benzo[f]isoindole-4,9-diones scaffold

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones

Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.

Oxaprozin Analogues as Selective RXR Agonists with Superior Properties and Pharmacokinetics

The retinoid X receptors (RXR) are ligand-activated transcription factors involved in multiple regulatory networks as universal heterodimer partners for nuclear receptors. Despite their high therapeutic potential in many pathologies, targeting of RXR has only been exploited in cancer treatment as the currently available RXR agonists suffer from exceptional lipophilicity, poor pharmacokinetics (PK), and adverse effects. Aiming to overcome the limitations and to provide improved RXR ligands, we developed a new potent RXR ligand chemotype based on the nonsteroidal anti-inflammatory drug oxaprozin. Systematic structure-activity relationship analysis enabled structural optimization toward low nanomolar potency similar to the well-established rexinoids. Cocrystal structures of the most active derivatives demonstrated orthosteric binding, and in vivo profiling revealed superior PK properties compared to current RXR agonists. The optimized compounds were highly selective for RXR activation and induced RXR-regulated gene expression in native cellular and in vivo settings suggesting them as excellent chemical tools to further explore the therapeutic potential of RXR.

Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP

An efficient and user-friendly palladium(II) precatalyst, POxAP (post-oxidative-addition precatalyst), was identified for use in Fukuyama cross-coupling reactions. Suitable for storage under air, the POxAP precatalyst allowed reaction between thioesters and organozinc reagents with turnover numbers of ～90000. A series of 23 ketones were obtained with yields ranging from 53 to 99%. As proof of efficacy, an alternative approach was developed for the synthesis of a key precursor of the natural product isoprekinamycin.

Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles

An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.

Alternative approach toward the generation of benzylic zinc reagent: Direct oxidative addition of active zinc into the carbon-oxygen bond of benzyl mesylates

The use of highly active zinc, prepared by the Rieke method, for the direct preparation of benzylic zinc mesylate was investigated. The oxidative addition of highly active zinc to benzyl mesylate was easily completed under mild conditions. The resulting benzylic zinc mesylates were employed in subsequent cross-coupling reactions with a broad range of electrophiles, and the formation of the corresponding products was successful.

Catalytic decarboxylative cross-ketonisation of aryl- and alkylcarboxylic acids using iron catalysts

In the presence of catalytic amounts of magnetite nanopowder, mixtures of aromatic and aliphatic carboxylic acids are converted selectively into the corresponding aryl alkyl ketones. As by-products, only carbon dioxide and water are released. This catalytic cross-ketonisation allows the regioselective acylation of aromatic systems and, thus, represents a sustainable alternative to Friedel-Crafts acylations.

Direct synthesis of arylketones by nickel-catalyzed addition of arylboronic acids to nitriles

A convenient and efficient method for the synthesis of various arylketones by nickel-catalyzed addition of arylboronic acids to nitriles is described. A catalytic cycle involving Ni(II) species as the catalytic intermediates is proposed to account for the present catalytic reaction.

Palladium-catalyzed carbonylative coupling of benzyl chlorides with aryl boronic acids in aqueous media

A novel chemoselective protocol for the carbonylative Suzuki coupling of benzyl chlorides with aryl boronic acids at low pressure of carbon monoxide has been developed. Applying a commercially available palladium acetate/PCy 3 catalyst system in the presence of potassium phosphate as the base and water as the solvent the coupling reactions proceeded smoothly. To demonstrate the general applicability 12 different α-arylated acetophenones have been synthesized in moderate to good yields (41-78%) under mild conditions.