16473-21-5

Basic information

• Product Name: Benzonitrile, 4-(fluoromethyl)-
• CAS NO: 16473-21-5
• Molecular Formula: C8H6FN
• Molecular Weight: 135.141
• Mol File: 16473-21-5.mol

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-(fluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(fluoromethyl)-(16473-21-5)
• EPA Substance Registry System: Benzonitrile, 4-(fluoromethyl)-(16473-21-5)

Safety Data

• Hazardous Substances Data: 16473-21-5(Hazardous Substances Data)

Upstream product

• 70135-28-3 (4-cyanophenyl)diazomethane 
• 87829-00-3 4-(hydrazonomethyl)benzonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 3058-39-7 4-iodobenzonitrile 
• 455-18-5 4-CF₃C₆H₄CN 
• 874-89-5 4-Cyanobenzyl alcohol 
• 373-52-4 bromofluoromethane 
• 126747-14-6 4-cyanophenylboronic acid 
• 373-53-5 fluoroiodomethane 
• 171364-82-2 4-cyanophenylboronic acid pinacol ester 
• 104-85-8 para-methylbenzonitrile 
• 17201-43-3 4-cyanobenzyl bromide 

Downstream Products

• 120427-54-5 4-(bromofluoromethyl)benzonitrile 
• 5462-71-5 4-cyanophenylacetic acid 
• 35505-99-8 (E) 3-(4-cyanophenyl)-1-phenyl-propene 
• 116450-83-0 4-(6-nitro-1-indolylmethyl)benzonitrile 
• 104-85-8 para-methylbenzonitrile 

Relevant articles and documents

The transmission of resonance effects through a methylene group-spectroscopic studies on some α-substituted-acetonitriles and p-toluonitriles

Frequencies and integrated intensities are recorded for the νCN mode of a representative selection of α-substituted acetonitriles, α-substituted-p-toluonitriles and β-substituted propionitriles.The frequencies of the acetonitriles are confirmed

PROCESSES FOR FLUORINATION

The present technology relates to fluorination reactions. Specifically, processes useful for making the fungicide compound, DFT are disclosed. More broadly, also disclosed herein are processes useful for deoxyfluorination at the α-aromatic position of a given compound.

METHOD AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

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.

Electrochemical-Promoted Nickel-Catalyzed Oxidative Fluoroalkylation of Aryl Iodides

This work describes a general strategy for metal-catalyzed cross-coupling of fluoroalkyl radicals with aryl halides under electrochemical conditions. The contradiction between anodic oxidation of fluoroalkyl sulfinates and cathodic reduction of low-valent nickel catalysts can be well addressed by paired electrolysis, allowing for direct introduction of fluorinated functionalities into aromatic systems.

Deoxyfluorination of alcohols with aryl fluorosulfonates

Aryl fluorosulfonates are developed as a deoxyfluorinating reagent in the transformation of primary and secondary alcohols into the corresponding alkyl fluorides. These reagents feature easy availability, low-cost, high stability and high efficiency. Diverse functionalities including aldehyde, ketone, ester, halogen, nitro, alkene, and alkyne are well tolerated under mild reaction conditions.

PROCESSES FOR FLUORINATION

The present technology relates to fluorination reactions. Specifically, processes useful for making the fungicide compound, DFT are disclosed. More broadly, also disclosed herein are processes useful for deoxyfluorination at the α-aromatic position of a given compound.

Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery

Molecular editing such as insertion, deletion, and single atom exchange in highly functionalized compounds is an aspirational goal for all chemists. Here, we disclose a photoredox protocol for the replacement of a single fluorine atom with hydrogen in electron-deficient trifluoromethylarenes including complex drug molecules. A robustness screening experiment shows that this reductive defluorination tolerates a range of functional groups and heterocycles commonly found in bioactive molecules. Preliminary studies allude to a catalytic cycle whereby the excited state of the organophotocatalyst is reductively quenched by the hydrogen atom donor, and returned in its original oxidation state by the trifluoromethylarene.

Cobalt-Catalyzed Asymmetric Cross-Coupling Reaction of Fluorinated Secondary Benzyl Bromides with Lithium Aryl Boronates/ZnBr2

A cobalt-catalyzed asymmetric cross-coupling of α-bromo-α-fluorotoluene derivatives with a variety of aryl zincates derived from lithium aryl n-butyl pinacol boronates and ZnBr2 under mild reaction conditions was described. In addition to mild reaction conditions, another advantage includes the compatibility of various common functional groups such as fluoride, chloride, bromide, cyano, or ester groups. Furthermore, this protocol was successfully applied to the enantioselective synthesis of three fluorinated derivatives of biologically active compounds or drug molecules.

Nucleophilic fluorination facilitated by a CsF-CaF2 packed bed reactor in continuous flow

A simple to prepare, dry and handle packed bed reactor carrying CsF on CaF2, towards nucleophilic fluorinations in continuous flow, is reported. The reactor also proved adaptable for silyl-ether deprotection and trifluoromethylations with Ruppert's reagent. The study includes reactor stability and scale-up investigations.