90446-25-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-(Difluoromethoxy)benzonitrile is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure, which includes fluorine atoms and a methoxy group, contributes to the development of new and effective compounds for medical and agricultural applications.
Used in Organic Light-Emitting Diodes (OLEDs) Industry:
In the field of OLED technology, 4-(Difluoromethoxy)benzonitrile is studied for its potential use in enhancing the performance of these devices. Its incorporation into OLED materials can lead to improved light emission properties and overall device efficiency.
Used in Technological Applications:
Beyond its use in pharmaceuticals and OLEDs, 4-(Difluoromethoxy)benzonitrile is also being explored for its potential in other technological applications. Its unique chemical properties may offer new possibilities for the development of innovative materials and devices in various industries.

InChI:InChI=1/C8H5F2NO/c9-8(10)12-7-3-1-6(5-11)2-4-7/h1-4,8H

Upstream product

• 75-45-6 Chlorodifluoromethane 
• 767-00-0 4-cyanophenol 
• 1895-39-2 sodium chlorodifluoroacetate 
• 1514-87-0 metyhyl chlorodifluoroacetate 
• 832114-08-6 N,N-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 354-08-5 bromodifluoroacetic acid 
• 75-46-7 trifluoromethan 

Downstream Products

• 1260433-01-9 (3-bromophenyl)(4-(difluoromethoxy)phenyl)methanimine 
• 1233181-65-1 C₁₃H₁₈F₂NO₄P 

Relevant academic research and scientific papers

Ortho-Dialkylamino arylboranes as efficient reagents for difluorocarbene trapping

Compounds bearing ortho-oriented dialkylamino and boryl groups can serve as efficient reagents to trap difluorocarbene leading to zwitterionic ammonium borates featuring N-CF2-B fragments. The reagents are shelf-stable and can be used as mechanistic probe

METALLOENZYME INHIBITOR COMPOUNDS

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

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.

Decarboxylative Trifluoromethylating Reagent [Cu(O2CCF3)(phen)] and Difluorocarbene Precursor [Cu(phen)2][O2CCF2Cl]

This article describes the new economic decarboxylative trifluoromethylating reagent [Cu(phen)(O2CCF3)] (1; phen=1,10-phenanthroline) and the efficient difluorocarbene precursor [Cu(phen)2][O2CCF2Cl] (2). Treatment of copper tert-butoxide with phen and subsequent addition of trifluoroacetic acid or chlorodifluoroacetic acid afforded air-stable complexes 1 and 2, respectively, which were characterized by X-ray crystallography. The copper(I) ion in 1 is coordinated by a bidentate phen ligand, a monodentate trifluoroacetate group, and a molecule of CH3CN in a distorted tetrahedral coordination geometry. The molecular structure of 2 adopts an ionic form that consists of a [Cu(phen)2]+ cation and a chlorodifluoroacetate anion. Complex 1 reacted with a variety of aryl and heteroaryl halides to form trifluoromethyl (hetero)arenes in good yields. The corresponding Hammett plot exhibited a linear relationship and a reaction parameter (ρ)=+0.56±0.02, which indicated that the trifluoromethylation reaction proceeded via a nucleophilic reactive species. Complex 2 reacts with phenols to produce aryl difluoromethyl ethers in modest-to-excellent yields. Mechanistic investigations revealed that the difluoromethylation reaction proceeds by initial copper-mediated formation of difluorocarbene and subsequent concerted addition of difluorocarbene to the phenol to form a three-center transition state.

Three step procedure for the preparation of aromatic and aliphatic difluoromethyl ethers from phenols and alcohols using a chlorine/fluorine exchange methodology

Difluoromethyl ethers are prepared from phenols in three steps via their respective formate ester derivatives. The formates are first converted to dichloromethyl ethers by treatment with PCl5. These ethers are then induced to undergo chlorine/fluorine exchange to form the respective difluoromethyl ethers. The chlorine/fluorine exchange is carried out by either a room temperature, solvolytic process using THF-5HF or Et3N-3HF as exchange medium, where HF is the ultimate source of fluorine, or by a direct displacement process in sulfolane at 125 C, where KF is the source of fluorine. By one or another of these processes, virtually all phenols, electron-rich and electron-poor, can be converted to their respective difluoromethyl ethers in good yields. Aliphatic alcohols are also able to be converted to their difluoromethyl ether derivatives using the Et3N-3HF exchange medium.

Use of fluoroform as a source of difluorocarbene in the synthesis of difluoromethoxy- and difluorothiomethoxyarenes

Fluoroform, CHF3, a non-ozone-depleting, nontoxic, and inexpensive gas can be used as a difluorocarbene source in a process for the conversion of phenols and thiophenols to their difluoromethoxy and difluorothiomethoxy derivatives. The reactions are carried out at moderate temperatures and atmospheric pressure, using potassium hydroxide as base in a two-phase (water/dioxane or water/acetonitrile) process to provide moderate to good yields of the respective products.

Heterosubstituted pyridine derivatives as PDE4 inhibitors

The invention encompasses the novel compound of Formula I useful in the treatment of diseases, including asthma, by raising the level of cyclic adenosine-3′,5′-monophosphate (cAMP) through the inhibition of phosphodiesterase IV (PDE 4). or a pharmaceutically acceptable salt or hydrate thereof. The invention also encompasses pharmaceutical compositions and methods for treatment.

Method for synthesis of aryl difluoromethyl ethers

This invention relates to a method for preparing difluoromethyl ethers, thiols and amines without using chlorofluorocarbon gases. The intermediates prepared by this method can be used to make certain compounds which act as PDE IV inhibitors which are useful for treating asthma and other diseases implicated with the PDE IV isozyme.

SYNTHESIS AND REACTIONS OF DIFLUOROMETHOXY- AND DIFLUOROCHLOROMETHOXY DERIVATIVES OF BENZENE

Difluoromethoxybenzaldehydes were synthesized by difluoromethylation of aromatic o- and p-hydroxyaldehydes by chladone-22 in alkaline medium.Chlorination of the difluoromethoxybenzene derivatives under illumination gave difluorochloromethoxy benzene with various function groups (F, Cl, CN, COCl, COOH).The values of the ?-constants of the OCF2Cl group have been determined.In its electronic characteristics it is similar to the OCF3 group.

Insecticidal substituted-biphenylmethyl oxime ethers

Oxime ethers of the formula STR1 wherein R1 is isopropyl, cyclopropyl, cyclopropylmethyl, or cyclobutyl; X and Y are independently halogen or straight or branched chain alkyl or alkoxy of 1 to 4 carbon atoms optionally substituted with one or more halogen atoms; n is 0-2; and m is 1-4 are disclosed. The insecticidal efficacy and preparation of the compounds are described and exemplified.