1644-72-0

Usage

Uses

Used in Organic Chemical Synthesis:
2-BROMOPHENYL TRIFLUOROMETHYL SULPHIDE 98 is used as an organic chemical synthesis intermediate for the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows it to serve as a valuable building block in the synthesis of complex organic molecules.
Used in Proteomics Research:
In the field of proteomics, 2-BROMOPHENYL TRIFLUOROMETHYL SULPHIDE 98 is utilized as a halogenated compound for studying protein structure, function, and interactions. Its presence enables researchers to investigate the properties of proteins and develop a better understanding of biological processes.
Used in Pharmaceutical Industry:
2-BROMOPHENYL TRIFLUOROMETHYL SULPHIDE 98 is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, 2-BROMOPHENYL TRIFLUOROMETHYL SULPHIDE 98 is employed as an intermediate in the synthesis of pesticides and other crop protection agents. Its incorporation into these products can enhance their effectiveness and selectivity, leading to better agricultural outcomes.
Used in Specialty Chemicals:
2-BROMOPHENYL TRIFLUOROMETHYL SULPHIDE 98 is also used in the production of specialty chemicals, such as dyes, fragrances, and other fine chemicals. Its unique structure and properties make it a versatile building block for creating novel and high-value chemical products.

InChI:InChI=1/C7H4BrF3S/c8-5-3-1-2-4-6(5)12-7(9,10)11/h1-4H

Upstream product

• 71112-91-9 bis(2-bromophenyl) disulfide 
• 2923-16-2 potassium trifluoroacetate 
• 108-86-1 bromobenzene 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 719-98-2 N-((trifluoromethyl)thio)isoindoline-1,3-dione 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 456-56-4 phenyl trifluoromethylsulfide 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 6320-02-1 o-bromothiophenol 
• 2926-29-6 Langlois reagent 
• 98-88-4 benzoyl chloride 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1395062-33-5 1-bromo-2-{[bromo(difluoro)methyl]sulfanyl}benzene 
• 2314-97-8 iodotrifluoromethane 

Downstream Products

• 60940-12-7 1-bromo-4-nitro-2-(trifluoromethylthio)benzene 
• 1309953-74-9 1-(trifluoromethylsulfanyl)-2-vinylbenzene 

Relevant academic research and scientific papers

A convenient synthesis of trifluoromethyl aryl sulfides

Trifluoromethyl aryl sulfides are obtained in moderate/good yields by heating potassium trifluoroacetate and aryl disulfides in sulfolane. Copyright (C) 1996 Elsevier Science Ltd.

Electrochemical Trifluoromethylation of Thiophenols with Sodium Trifluoromethanesulfinate

We developed an electrochemical trifluoromethylation of thiophenols without the use of metal catalysts and oxidants. This reaction features mild reaction conditions, readily available substrate, as well as moderate to good yields. In addition, this protocol can be easily scaled up with moderate efficiency.

S-(Trifluoromethyl)Benzothioate (TFBT): A KF-Based Reagent for Nucleophilic Trifluoromethylthiolation

S-(Trifluoromethyl)benzothioate (TFBT) has been developed as an inexpensive, bench-stable, and user-friendly trifluoromethylthiolation reagent, which can be easily synthesized by using KF as the only fluorine source. By using TFBT, trifluoromethylthiolates with various counterions can be readily obtained. The synthetic application of TFBT was demonstrated by trifluoromethylthiolation-halogenation of arynes, bis(trifluoromethylthiolation)–halogenation of 1,2-benzdiynes, nucleophilic substitution of alkyl halides, deoxytrifluoromethylthiolation of alcohols, and cross-coupling with aryl and vinyl boronic acids.

Fluorodecarboxylation: Synthesis of aryl trifluoromethyl ethers (ArOCF3) and thioethers (ArSCF3)

Fluorodecarboxylation of aryloxydifluoroacetic acid (ArOCF2CO2H) and arylmercaptodifluoroacetic acid (ArSCF2CO2H) towards ArXCF3 (X = O, S) using silver (I) salts in the presence of Selectfluor in a biphasic system with trifluoroacetic acid additive is discussed.

Copper-Catalyzed Trifluoromethylthiolation of Di(hetero)aryl-λ3-iodanes: Mechanistic Insight and Application to Synthesis of (Hetero)Aryl Trifluoromethyl Sulfides

The direct and regioselective copper/S-Phos-catalyzed trifluoromethylthiolation of symmetrical and unsymmetrical di(hetero)aryl-λ3-iodanes has been accomplished for the synthesis of various (hetero)aryl trifluoromethyl sulfides employing readily accessible silver trifluoromethylthiolate (AgSCF3) as nucleophilic trifluoromethylthiolating reagent. The developed transformation tolerates various functional groups like nitrile, enolizable ketone, ester, nitro and free carboxylic acid. Interestingly, the formal trifluoromethylthiolation of arenes was also achieved through integration of the synthesis of diaryl-λ3-iodanes from arenes with the trifluoromethylthiolation. Mechanistic investigations did not favor the radical formation and SET pathway. Based on the variable temperature 19F NMR spectroscopy, isolation of the most relevant catalytic intermediate, and stoichiometric studies supported the Cu(I)/Cu(III) catalytic cycle, wherein the oxidative addition of diaryl-λ3-iodanes was assisted by the silver salt.

18F-Labeling of Aryl-SCF3, -OCF3 and -OCHF2 with [18F]Fluoride

We report that halogenophilic silver(I) triflate permits halogen exchange (halex) nucleophilic 18F-fluorination of aryl-OCHFCl, -OCF2Br and -SCF2Br precursors under mild conditions. This AgI-mediated process allows for the first time access to a range of 18F-labeled aryl-OCHF2, -OCF3 and -SCF3 derivatives, inclusive of [18F]riluzole. The 18F-labeling of these medicinally important motifs expands the radiochemical space available for PET applications. A halogen exchange (halex) 18F-fluorination process offers access for the first time to 18F-labeled arylOCF3, arylOCHF2 and arylSCF3, three motifs of established medicinal importance in PET radiotracers. The use of silver(I) triflate is critical to permit 18F-labeling under mild conditions.

Catalytic borylation of SCF3-functionalized arenes by rhodium(I) boryl complexes: Regioselective C-H activation at the ortho-position

An unprecedented reaction pathway for the borylation of SCF 3-containing arenes using [Rh(Bpin)(PEt3)3] (pin=pinacolato) is reported. Catalytic processes were developed and the functionalizations proceed under mild reaction conditions. The C-H activations occur with a unique regioselectivity for the position ortho to the SCF 3 group, which apparently serves as directing group. Borylated SCF3 compounds can serve as versatile building blocks. SCF 3 building blocks: A unique reaction route allows access to SCF 3-functionalized arenes, which are borylated at the ortho-position. The functionalization proceeds by C-H borylation with [Rh(Bpin)(PEt 3)3] (pin=pinacolato), and the SCF3 group likely serves as directing group. The generated borylated SCF3 compounds are versatile building blocks for further transformations.

Direct catalytic trifluoromethylthiolation of boronic acids and alkynes employing electrophilic shelf-stable N-(trifluoromethylthio)phthalimide

A new and safe method for the synthesis of N-(trifluoromethylthio) phthalimide, a convenient and shelf-stable reagent for the direct trifluoromethylthiolation, has been developed. N-(Trifluoromethylthio) phthalimide can be used as an electrophilic source of F3CS + and reacts readily with boronic acids and alkynes under copper catalysis. The utility of CF3S-containing molecules as biologically active agents, the mild reaction conditions employed, and the high tolerance of functional groups demonstrate the potential of this new methodology to be widely applied in organic synthesis as well as industrial pharmaceutical and agrochemical research and development. Shelf life: A new and safe method for the synthesis of N-(trifluoromethylthio)phthalimide has been developed. It serves as a convenient and shelf-stable reagent for the direct copper-catalyzed trifluoromethylthiolation of readily available boronic acids and alkynes. Copyright

Convenient synthesis and isolation of trifluoromethylthio-substituted building blocks

Various aryl-, heteroaryl-, and alkyl mercaptanes (RSH, 1a-r) were treated with a slight excess of NaH suspended in DMF to make the appropriate sodium thiolates (RSNa), which then reacted with 1.3 equivalent of CF3I at room temperature for overnight to afford the appropriate trifluoromethyl sulfides (CF3SR, 2) in fair to good yields. The radical chain alkylation reaction was effective without the use of UV irradiation with all but three substrates (thiosalicylic acid, 1k; 2-mercaptobenzimidazole, 1q; and 3-mercaptopropionic acid, 1r). Steam-distillation was found as an effective and easy to upscale means for the isolation of these volatile and water immiscible sulfides. The CF3I reagent gas was conveniently weighed and delivered to the reaction mixture by the balloon technique or as a preliminary made stock solution in DMF or DMSO. The sulfides 2 obtained here were assayed by GC and characterized by 1H, 13C, 19F NMR and MS spectroscopy.