83882-67-1

Usage

Uses

Used in Pharmaceutical Industry:
4-(Difluoromethoxy)acetophenone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications. Its unique chemical structure allows for the creation of molecules with specific properties, enhancing the efficacy and safety of medications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(Difluoromethoxy)acetophenone serves as an essential intermediate for the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds aids in the development of more effective and environmentally friendly solutions for crop protection and management.
Used in Organic Synthesis:
4-(Difluoromethoxy)acetophenone is utilized as a versatile building block in organic synthesis for the preparation of a wide range of organic compounds. Its reactivity and functional groups make it suitable for various chemical reactions, leading to the formation of molecules with diverse applications in different industries, including the synthesis of fragrances, dyes, and other specialty chemicals.
Used in Research and Development:
4-(DIFLUOROMETHOXY)ACETOPHENONE is also employed in research and development settings as a valuable tool for exploring new chemical reactions and pathways. Its unique properties and reactivity make it an attractive candidate for studying novel synthetic methods and understanding the underlying mechanisms of various chemical processes.

InChI:InChI=1/C3H2F6O/c4-1(5)2(6)10-3(7,8)9/h1-2H

Upstream product

• 75-45-6 Chlorodifluoromethane 
• 99-93-4 4-Hydroxyacetophenone 
• 60-29-7 diethyl ether 
• 115262-01-6 [bromo(difluoro)methyl]-trimethyl-silane 
• 354-08-5 bromodifluoroacetic acid 
• 667-27-6 Ethyl bromodifluoroacetate 
• 98-86-2 acetophenone 
• 431-03-8 dimethylglyoxal 
• 128140-82-9 1-(difluoromethoxy)-4-iodobenzene 
• 1895-39-2 sodium chlorodifluoroacetate 

Downstream Products

• 141134-24-9 1-(4-difluoromethoxyphenyl)-2-bromoethan-1-one 
• 136123-72-3 dl-α-methyl-4-difluoromethoxybenzylamine 
• 149774-14-1 1-(4-difluoromethoxy-phenyl)-ethanone oxime 
• 105512-78-5 4-(4-difluoromethoxyphenyl)-thiazol-2-ylamine 
• 1180015-71-7 C₁₅H₁₃BrF₂O₂ 
• 316806-56-1 5-(4-(difluoromethoxy)phenyl)-5-methylimidazolidine-2,4-dione 
• 1391571-43-9 (S)-2-amino-2-(4-difluoromethoxy-phenyl)ethanol hydrochloride 
• 1514883-00-1 C₉H₈F₂O₃ 
• 1574396-97-6 C₁₉H₃₃F₂NO₃SSi 
• 1574396-96-5 C₁₉H₃₁F₂NO₃SSi 
• 1574396-95-4 C₁₅H₂₂F₂O₃Si 
• 1574396-42-1 3-(tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-1-(4-difluoromethoxy-phenyl)-2-hydroxy-ethyl]-amide 

Relevant academic research and scientific papers

Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C?H Di- and Trifluoromethoxylation

Applications of TEMPO. catalysis for the development of redox-neutral transformations are rare. Reported here is the first TEMPO.-catalyzed, redox-neutral C?H di- and trifluoromethoxylation of (hetero)arenes. The reaction exhibits a broad substrate scope, has high functional-group tolerance, and can be employed for the late-stage functionalization of complex druglike molecules. Kinetic measurements, isolation and resubjection of catalytic intermediates, UV/Vis studies, and DFT calculations support the proposed oxidative TEMPO./TEMPO+ redox catalytic cycle. Mechanistic studies also suggest that Li2CO3 plays an important role in preventing catalyst deactivation. These findings will provide new insights into the design and development of novel reactions through redox-neutral TEMPO. catalysis.

Catalytic radical difluoromethoxylation of arenes and heteroarenes

Intermolecular C-H difluoromethoxylation of (hetero)arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a redox-active difluoromethoxylating reagent 1a and photoredox catalysts for the direct C-H difluoromethoxylation of (hetero)arenes. Our approach is operationally simple, proceeds at room temperature, and uses bench-stable reagents. Its synthetic utility is highlighted by mild reaction conditions that tolerate a wide variety of functional groups and biorelevant molecules. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1a forming a neutral radical intermediate that liberates the OCF2H radical exclusively. Addition of this radical to (hetero)arenes gives difluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of difluoromethoxylation.

DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME

The present invention provides a compound having the structure (I), a processing of making the compound; and a process of using the compound as a reagent for the difluoromethoxylation and trifluoromethoxylation of arenes or heteroarenes.

Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones

The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. Herein, we describe a simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atmosphere. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields.

Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation

In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).

METALLOENZYME INHIBITOR COMPOUNDS

Provided are compounds having HDAC6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by HDAC6.

Difluoro methylation reagent, preparation method and application thereof (by machine translation)

The present invention discloses a two-trifluoromethylation of the reagent, preparation method and application thereof. The invention [...] methylation reagent preparation process is simple, high yield; and the reagent can be a more moderate, high-efficiently the sulfonic acid, alcohol, carbonyl and on the α carbon atom of the difluoromethyl. (by machine translation)

Visible-Light Photoredox Difluoromethylation of Phenols and Thiophenols with Commercially Available Difluorobromoacetic Acid

A simple and efficient visible-light photoredox one-pot method for difluoromethylation of phenols and thiophenols has been developed. The protocol uses commercially available, inexpensive, and easy handling difluorobromoacetic acid as the difluoromethylating agent, and the diverse O- and S-difluoromethylated products were prepared in good yields with tolerance of many functional groups.

Synthesis of gem-difluorocyclopropa(e)nes and O-, S-, N-, and P-difluoromethylated compounds with TMSCF2Br

Two-in-one: Me3SiCF2Br is an efficient difluorocarbene source and is compatible with both neutral and aqueous basic conditions. Bromide-ion-initiated [2+1] cycloaddition with alkenes/alkynes and hydroxide ion promoted α-addition with (thio)phenols, (thio)alcohols, sulfinates, heterocyclic amines, and H-phosphine oxides give the corresponding gem-difluorinated compounds with broad functional-group tolerance. Copyright

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.