55805-13-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyano-alpha,alpha-difluorotoluene and 3-Cyanobenzal fluoride are used as building blocks and intermediates in the synthesis of various pharmaceuticals. They contribute to the development of new drugs and improve the efficacy and properties of existing medications.
Used in Agrochemical Industry:
These chemicals are also utilized in the production of agrochemicals, such as pesticides and herbicides. They help in the development of more effective and environmentally friendly products for agricultural applications.
Used in Chemical Industry:
3-Cyano-alpha,alpha-difluorotoluene and 3-Cyanobenzal fluoride are used in the manufacturing of dyes, pigments, and polymers. They play a crucial role in enhancing the properties and performance of these materials, leading to a wide range of applications in various industries.
Used in Specialty Chemicals:
These chemicals are employed as raw materials in the synthesis of specialty chemicals, which have unique properties and applications in specific industries, such as electronics, materials science, and biotechnology.

Upstream product

• 24964-64-5 3-Cyanobenzaldehyde 
• 1511-62-2 bromodifluoromethane 
• 150255-96-2 (3‐cyanophenyl)boronic acid 
• 718640-74-5 3-cyanophenylboronic acid ethylene glycol ester 
• 75-45-6 Chlorodifluoromethane 
• 6952-59-6 3-cyanobromobenzene 
• 667-27-6 Ethyl bromodifluoroacetate 
• 69113-59-3 3-iodobenzonitrile 
• 1249788-93-9 2-(3-cyanophenyl)-2,2-difluoro acetic acid ethyl ester 
• 1249974-01-3 2-(3-cyanophenyl)-2,2-difluoroacetic acid 

Downstream Products

• 55805-20-4 3-(difluoromethyl)benzoic acid 
• 1402454-41-4 3-difluoromethyl-N-methoxy-N-methylbenzamide 
• 1220696-59-2 3-(difluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 

Relevant academic research and scientific papers

Visible-light photoredox-catalyzed selective carboxylation of C(sp3)?F bonds with CO2

It is highly attractive and challenging to utilize carbon dioxide (CO2), because of its inertness, as a nontoxic and sustainable C1 source in the synthesis of valuable compounds. Here, we report a novel selective carboxylation of C(sp3)?F bonds with CO2 via visible-light photoredox catalysis. A variety of mono-, di-, and trifluoroalkylarenes as well as α,α-difluorocarboxylic esters and amides undergo such reactions to give important aryl acetic acids and α-fluorocarboxylic acids, including several drugs and analogs, under mild conditions. Notably, mechanistic studies and DFT calculations demonstrate the dual role of CO2 as an electron carrier and electrophile during this transformation. The fluorinated substrates would undergo single-electron reduction by electron-rich CO2 radical anions, which are generated in situ from CO2 via sequential hydride-transfer reduction and hydrogen-atom-transfer processes. We anticipate our finding to be a starting point for more challenging CO2 utilization with inert substrates, including lignin and other biomass.

Nickel-Catalyzed Difluoromethylation of Arylboronic Acids with Bromodifluoromethane

Although bromodifluoromethane (BrCF2H) is a simple and readily available fluorine source, direct formation of difluoromethylated arenes with BrCF2H has not been reported. Herein, we describe an efficient method to access difluoromethylated arenes through a nickel-catalyzed difluoromethylation of arylboronic acids with BrCF2H. The reaction exhibits high efficiency, good functional group tolerance and broad substrate scope, thus providing an efficient route for applications in drug discovery and development. Preliminary mechanistic studies reveal that a difluoromethyl radical is involved in the reaction.

Method for preparing alpha-aryl/heteroaryl/alkenyl-alpha,alpha-difluoromethyl compounds

The invention discloses a method for preparing alpha-aryl/heteroaryl/alkenyl-alpha,alpha-difluoromethyl compounds. The preparation method for the alpha-aryl/heteroaryl/alkenyl-alpha,alpha-difluoromethyl compounds as shown in a formula C which is described

Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones

We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction between iodane and hydrazone. This is the first use of non-α-stabilized diazo compounds in this reaction, which provided an efficient synthesis of aryldifluoromethane (ArCHF2) and aryldichloromethane (ArCHCl2) derivatives. (Figure presented.).

Chlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium

Difluoromethylated aromatic compounds are of increasing importance in pharmaceuticals, agrochemicals and materials. Chlorodifluoromethane (ClCF2H), an inexpensive, abundant and widely used industrial raw material, represents the ideal and most straightforward difluoromethylating reagent, but introduction of the difluoromethyl group (CF2H) from ClCF2H into aromatics has not been reported. Here, we describe a direct palladium-catalysed difluoromethylation method for coupling ClCF2H with arylboronic acids and esters to generate difluoromethylated arenes with high efficiency. The reaction exhibits a remarkably broad substrate scope, including heteroarylboronic acids, and was used for difluoromethylation of a range of pharmaceuticals and biologically active compounds. Preliminary mechanistic studies revealed that a palladium difluorocarbene intermediate is involved in the reaction. Although numerous metal-difluorocarbene complexes have been prepared, the catalytic synthesis of difluoromethylated or difluoromethylenated compounds involving metal-difluorocarbene complexes has not received much attention. This new reaction therefore also opens the door to understand metal- difluorocarbene complex catalysed reactions.

Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent

The palladium-catalyzed Negishi cross-coupling reaction of aryl iodides and bromides with (difluoromethyl)zinc reagent bearing a diamine such as TMEDA is achieved to provide the difluoromethylated aromatic compounds in good to excellent yields. The advantages of (difluoromethyl)zinc reagent are that (1) the derivatives, which possess different stability and reactivity, can be readily prepared via ligand screening and (2) transmetalation of a difluoromethyl group from the zinc reagent to palladium catalyst efficiently proceeds without an activator.

Access to Difluoromethylated Arenes by Pd-Catalyzed Reaction of Arylboronic Acids with Bromodifluoroacetate

An unprecedented example of Pd-catalyzed difluoromethylation of aryl boronic acids with bromodifluoroacetate is described. The reaction proceeds under mild reaction conditions with hydroquinone and Fe(acac)3 as additives. Preliminary mechanistic studies reveal that a difluorocarbene pathway is involved in the reaction, which is unusual compared to the most traditional approaches. This reaction has advantages of high efficiency and excellent functional group compatibility, even toward bromide and hydroxy group, thus providing a useful protocol for drug discovery and development.

NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS

Heteroaromatic compounds of Formula I: are HIV reverse transcriptase inhibitors, wherein R1, R2, R3, R4 and R5 are defined herein. The compounds of Formula I and their pharmaceutically acceptable salt

A new method for aromatic difluoromethylation: Copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides

A new methodology for aromatic difluoromethylation is described. Aryl iodides reacted with α-silyldifluoroacetates upon treatment with copper catalyst in DMSO or DME to give the corresponding aryldifluoroacetates in moderate to good yields. The subsequent hydrolysis of aryldifluoroacetates and KF-promoted decarboxylation afforded a variety of difluoromethyl aromatics.

Phenylglycinamide and pyridylglycinamide derivatives useful as anticoagulants

The present invention provides novel phenylglycinamide derivatives of Formula (I) or (IV): or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein the variables W, W1, Y, Z, R7, R8, R9, and R11 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.