78031-08-0

Basic information

• Product Name: Benzene, [(bromodifluoromethyl)thio]-
• CAS NO: 78031-08-0
• Molecular Formula: C7H5BrF2S
• Molecular Weight: 239.084
• Mol File: 78031-08-0.mol

Chemical Properties

• CAS DataBase Reference: Benzene, [(bromodifluoromethyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(bromodifluoromethyl)thio]-(78031-08-0)
• EPA Substance Registry System: Benzene, [(bromodifluoromethyl)thio]-(78031-08-0)

Safety Data

• Hazardous Substances Data: 78031-08-0(Hazardous Substances Data)

Upstream product

• 75-61-6 dibromodifluoromethane 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 353-59-3 halon-1211 
• 58201-66-4 (bromodifluormethyl)triphenylphosphonium bromide 

Downstream Products

• 776313-42-9 1,1-difluoro-3-phenylpropyl phenyl sulfide 
• 776313-44-1 allyl 4,4-difluoro-2-methyl-4-phenylsulfanylbutanoate 
• 272788-38-2 iododifluoromethyl phenyl thioether 
• 1395062-13-1 S-bromodifluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium triflate 
• 1352812-07-7 S-phenyl 1-methyl-1H-pyrrole-2-carbothioate 
• 54429-67-3 (E)-3-(4-Methoxy-phenyl)-thioacrylic acid S-phenyl ester 
• 1422023-82-2 S-phenyl 3,3-diphenylprop-2-enethioate 

Relevant articles and documents

An easier and quicker access to (benzenesulfonyl)difluoromethanesulfenamide reagent

(Benzenesulfonyl)difluoromethanesulfenamide (PhSO2-BB12H) is an interesting reagent to lead to various fluoroalkylselenotated molecules. This compound is obtained from [(benzenesulfonyl)difluoromethyl]trimethylsilane. Herein, a new process in two steps, w

Efficient nucleophilic difluoromethylation of aldehydes with (phenylsulfonyl)difluoromethylzinc and (phenylsulfonyl)difluoromethylcadmium reagents

A new strategy for nucleophilic addition to aldehydes with difluoromethyl organometallic reagents has been developed by functionalizing the difluoromethyl moiety with the phenylsulfonyl group (SO2Ph). This electron-withdrawing group influences

Visible-Light-Induced Arylthiofluoroalkylations of Unactivated Heteroaromatics and Alkenes

Visible-light-induced arylthiofluoroalkylations of unactivated heteroaromatics and alkenes have been developed utilizing readily available arylthiofluoroalkyl sources. This method enables simultaneous installation of sulfur and fluoroalkyl moieties, two important functional groups, which demonstrates its potential use for late-stage modifications in the synthesis of functional molecules. This method can be easily utilized to fine-tune the properties of lead molecules in drug development by controlling the number of fluorine atoms in the reagents.

Direct Electrophilic (Benzenesulfonyl)Difluoromethylthiolation with a Shelf-Stable Reagent

The (benzenesulfonyl)difluoromethylsulfanyl (PhSO2CF2S) group is a valuable substituent with specific properties which can provide access to new applications of fluoroalkylthiolated compounds. Direct introduction of this moiety can be performed by in an electrophilic manner by using a new shelf-stable reagent, namely a (benzenesulfonyl)difluoromethanesulfenamide. Furthermore, mild magnesium-mediated reduction of the PhSO2CF2S group leads to a facile synthesis of difluoromethylthiolated molecules and their deuterated analogs. Chameleon-like reactivity: (Benzenesulfonyl)difluoromethanesulfenamide was developed as a new, shelf-stable reagent for the introduction of the PhSO2CF2S group into organic molecules (see scheme). The versatility of the PhSO2 moiety also provides an entry into reductive deuterations.

α-(Difluoromethyl)styrene: Improved approach to grams scale synthesis

Improved, efficient, grams scale synthesis of α-(difluoromethyl)styrene (DFMST) based on nucleophilic difluoromethylation process using difluoromethylphenyl sulfone, is presented. Difluoromethylating agent (PhSO2CF2H) was obtained in two-step synthetic sequence with 69% overall yield. Three-step DFMST synthetic route was easily implemented for the preparation of gram quantities of the monomer, allowing for polymerization studies. The syntheses were based on the use of commercially available and reasonable in price starting materials and reagents.

Electrophilic difluoro(phenylthio)methylation: Generation, stability, and reactivity of α-fluorocarbocations

Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of α-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2+).

Palladium-mediated heck-type reactions of [(Bromodifluoromethyl)sulfonyl] benzene: Synthesis of α-alkenyl- and α-heteroaryl-substituted α,α-difluoromethyl phenyl sulfones

Palladium-catalyzed Heck-type reactions of [(bromodifluoromethyl)sulfonyl] benzene (1) with styrene derivatives and heteroaromatic compounds successfully gave α-alkenyl- and α-heteroaryl-substituted α,α- difluoromethyl phenyl sulfones, respectively. Palladium-catalyzed Heck-type reactions of [(bromodifluoromethyl)sulfonyl]benzene (1) are reported. Both styrene derivatives and heteroaromatic compounds gave PhSO2CF 2-substituted products in moderate to good yields.

Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents

A series of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts 1 were readily synthesized by treatment of corresponding (bromodifluoromethyl) arylsulfoxides 2 and substituted benzenes 3 with triflic anhydride in moderate to good yields. The unsymmetrical sulfonium salts 1 with different aryl groups having electron-donating or electron-withdrawing substituents can be nicely constructed depending on the choice of 2 and 3. Bromodifluoromethylation of alkynes was evaluated by using the selected diarylsulfonium salts 1 to provide the desired bromodifluoromethylated alkynes in moderate to good yields.

COMPOUNDS AND COMPOSITIONS AS TRK INHIBITORS

The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with abnormal or deregulated TRK kinase activity.

Friedel-crafts-type alkylation with bromodifluoro(phenylsulfanyl)methane through α-fluorocarbocations: Syntheses of thioesters, benzophenones and xanthones

Bromodifluoro(phenylsulfanyl)methane undergoes a Friedel-Crafts-type alkylation, through α-fluorocarbocations, with activated aromatic compounds yielding thioesters and/or benzophenones. The methodology has been applied to the synthesis of naturally occurring xanthone derivatives.