867367-02-0

Usage

Uses

Used in Pharmaceutical Industry:
3,5-diMethyl-4-fluorobenzonitrile is used as a synthetic intermediate for the development of pharmaceuticals, contributing to the creation of new drugs and therapeutic agents. Its unique molecular structure allows for the synthesis of a wide range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 3,5-diMethyl-4-fluorobenzonitrile is utilized as a key intermediate in the synthesis of various agrochemicals, including pesticides and herbicides. Its incorporation aids in enhancing the effectiveness of these products in agricultural applications.
Used in Dye and Pigment Production:
3,5-diMethyl-4-fluorobenzonitrile is employed as a building block in the manufacturing of dyes and pigments. Its chemical properties enable the production of a diverse array of colorants used in various industries, such as textiles, plastics, and printing inks.
Used in Organic Compound Synthesis:
3,5-diMethyl-4-fluorobenzonitrile also serves as a valuable building block in the synthesis of various organic compounds. Its presence in the molecular structure of these compounds allows for the development of new materials with unique properties and applications.

InChI:InChI=1S/C9H8FN/c1-6-3-8(5-11)4-7(2)9(6)10/h3-4H,1-2H3

Upstream product

• 955929-58-5 4-cyano-2,6-dimethylphenyl trifluoromethanesulfonate 
• 557-21-1 zinc(II) cyanide 
• 443-88-9 2-fluoro-m-xylene 
• 7321-55-3 2,2-dimethylmalononitrile 
• 99725-44-7 3,5-dimethyl-4-fluoro-1-bromobenzene 
• 99-93-4 4-Hydroxyacetophenone 
• 4198-90-7 3,5-dimethyl-4-hydroxybenzonitrile 
• 1147894-98-1 2-(4-fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1056155-67-9 C₁₉H₁₈ClNO₃ 

Relevant academic research and scientific papers

Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes

Aromatic nitriles are key structural units in organic chemistry and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting commercially available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches.

1,4-Dicarbofunctionalization of 4-Fluoroaryl Grignard and Lithium Reagents with Disubstituted Malononitriles

An efficient one-pot 1,4-dicarbofunctionalization of 4-fluoroaryl Grignard or lithium reagents with 2,2-disubstituted malononitriles is described. The reaction proceeds by sequential transnitrilation and SNAr reactions. Commercial Grignard solutions, Grignard reagents prepared in situ by halogen/magnesium exchange with i-PrMgCl, or aryllithium reagents prepared in situ by bromine/lithium exchange with n-BuLi are compatible with the reaction conditions. Moreover, 2,2-disubstituted malononitriles of diverse structures are accommodated. The reaction provides a unique approach to 1,4-dicarbofunctionalization of activated arenes in a tandem, one-pot transformation.

Phosphine-Ligated Palladium Sulfonate Palladacycles

Described are palladium precatalysts, and methods of making and using them. The palladium precatalysts show improved stability and improved reactivity in comparison to previously-described palladium precatalysts.

One-pot, two-step, microwave-assisted palladium-catalyzed conversion of aryl alcohols to aryl fluorides via aryl nonaflates

A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.

Accelerating palladium-catalyzed C-F bond formation: Use of a microflow packed-bed reactor

A flow process for Pd-catalyzed C-F bond formation is described. A microreactor with a packed-bed design allows for easy handling of large quantities of insoluble CsF with precise control over reaction times, efficient mixing, and the ability to safely handle elevated temperatures and pressures. A variety of aryl triflates, including heteroaryl ones, were converted into aryl fluorides in short reaction times (see scheme).

Cyanation of arenes via iridium-catalyzed borylation

We report a method to conduct one-pot meta cyanation of arenes by iridium-catalyzed C-H borylation and copper-mediated cyanation of the resulting arylboronate esters. This process relies on a method to conduct the cyanation of arylboronic esters, and conditions for this new transformation are reported. Conditions for the copper-mediated cyanation of arylboronic acids are also reported. By the resulting sequence of borylation and cyanation, 1,3-disubstituted and 1,2,3-trisubstituted arenes and heteroarenes containing halide, ketone, ester, amide, and protected alcohol functionalities are converted to the corresponding meta-substituted aryl nitriles. The utility of this methodology is demonstrated through the conversion of a protected 2,6-disubstituted phenol to 4-cyano-2,6-dimethylphenol, which is an intermediate in the synthesis of the pharmaceutical etravirine. The utility of the method is further demonstrated by the conversion of 3-chloro-5-methylbenzonitrile, produced through the one-pot C-H borylation and cyanation sequence, to the corresponding 3,5-disubstituted aldehydes, ketones, amides, carboxylic acids, tetrazoles, and benzylamines.