66865-75-6

Basic information

• Product Name: 4-methyl-α,α-difluorotoluene
• Synonyms: 4-methyl-α,α-difluorotoluene
• CAS NO: 66865-75-6
• Molecular Weight: 142.148
• Mol File: 66865-75-6.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 4-methyl-α,α-difluorotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-α,α-difluorotoluene(66865-75-6)
• EPA Substance Registry System: 4-methyl-α,α-difluorotoluene(66865-75-6)

Safety Data

• Hazardous Substances Data: 66865-75-6(Hazardous Substances Data)

Upstream product

• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 1219454-89-3 2-((difluoromethyl)sulfonyl)pyridine 
• 15106-88-4 di(p-tolyl)zinc 
• 106-38-7 para-bromotoluene 
• 1493-03-4 iododifluoromethane 
• 56228-54-7 2-((difluoromethyl)sulfonyl)-4,6-dimethylpyrimidine 
• 195062-57-8 p-tolylboronic pinacol ester 
• 6140-17-6 4-methylbenzotrifluoride 
• 106-43-4 para-chlorotoluene 
• 1511-62-2 bromodifluoromethane 
• 52693-87-5 4-methylbenzaldehyde hydrazone 
• 3429-52-5 2,2,3-trimethyl-2-silabutane 
• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 

Relevant articles and documents

Arylsulfur trifluorides: Improved method of synthesis and use as in situ deoxofluorination reagents

Building on recent results of Umemoto and Winter, an improved method of synthesis of arylsulfur trifluorides, including the excellent, new deoxofluorination reagent Fluolead, is hereby reported. The method utilizes Br2 and KF as oxidizing and fluorinating reagents for efficient, high yield conversion of aryl disulfides and mercaptans to arylsulfur trifluorides. It has also been shown that both Fluolead and mesitylsulfur trifluoride may be generated in acetonitrile and used as in situ deoxofluorination reagents for conversion of either aldehydes or ketones to their respective gem-difluoro compounds. An analysis of the probable mechanism of action, including computational efforts, allows postulation of a rationale for the highly variable reactivities of different arylsulfur trifluorides as deoxofluorination reagents.

Iron-Catalyzed Fluoroalkylation of Arylborates with Sulfone Reagents: Beyond the Limitation of Reduction Potential

The iron-catalyzed alkyl–aryl coupling reaction between sulfones and arylboron compounds has remained a challenge. We report the first iron-catalyzed radical difluoroalkylation of arylborates with N-heteroaryl sulfones. The coordination between the iron catalyst and the nitrogen atom of N-heteroaryl sulfones was identified to be important in overcoming the reduction potential limitation of sulfones in the intermolecular single-electron-transfer process, which enables both fluoroalkyl N-heteroaryl sulfones (with relatively high reduction potentials) and nonfluorinated alkyl N-heteroaryl sulfones (with low reduction potentials) to serve as powerful alkylation reagents.

Frustrated Lewis-Pair-Meditated Selective Single Fluoride Substitution in Trifluoromethyl Groups

Single fluoride substitution in trifluoromethylarenes is an ongoing synthetic challenge that often leads to "over-reaction", where multiple fluorides are replaced. Development of this reaction would allow simple access to a vast range of difluoromethyl derivatives of current interest to pharmaceutical, agrochemistry, and materials sciences. Using a catalytic frustrated Lewis pair approach, we have developed a generic protocol that allows a single substitution of one fluoride in trifluoromethyl groups with neutral phosphine and pyridine bases. The resulting phosphonium and pyridinium salts can be further functionalized via nucleophilic substitution, photoredox coupling, and electrophilic transfer reactions allowing the generation of a vast array of difluoromethyl products.