456-56-4

Usage

Uses

Used in Chemical Synthesis:
Trifluoromethylthiobenzene is used as an intermediate in the preparation of various organic compounds, such as sulfoxides, dithiane dioxide, and dithiolane dioxide. It is involved in iron-catalyzed oxidation reactions of sulfides, dithiane, or dithiolane with hydrogen peroxide, which allows for the formation of these valuable products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trifluoromethylthiobenzene is used as a building block for the synthesis of bioactive molecules and drug candidates. Its unique trifluoromethylthio group can impart specific properties to the final drug molecule, such as increased lipophilicity, metabolic stability, and binding affinity to target proteins.
Used in the Synthesis of Fluorinated Compounds:
Trifluoromethylthiobenzene is also used in the synthesis of fluorinated compounds, such as trifluoroand difluoromethylsilanes. These compounds are obtained through reductive coupling reactions of fluoromethyl sulfones, sulfoxides, and sulfides with chlorosilanes. The resulting fluorinated compounds have potential applications in various fields, including materials science, agrochemistry, and pharmaceuticals.
Used in the Preparation of Benzophenone Hydrazone Derivatives:
Furthermore, trifluoromethylthiobenzene is utilized in the preparation of benzophenone hydrazone derivatives. These derivatives are important in organic chemistry as they can act as precursors to various heterocyclic compounds and have potential applications in the synthesis of pharmaceuticals, dyes, and other organic compounds.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 4047, 1985 DOI: 10.1021/jo00221a017Synthesis, p. 721, 1975 DOI: 10.1055/s-1975-23905

InChI:InChI=1/C7H5F3S/c8-7(9,10)11-6-4-2-1-3-5-6/h1-5H

Upstream product

• 2923-16-2 potassium trifluoroacetate 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 701-65-5 (trichloromethylthio)benzene 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 372-16-7 thioorthocarbonotrifluoridic acid 4-amino-phenyl ester 
• 2314-97-8 iodotrifluoromethane 
• 108-86-1 bromobenzene 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 591-50-4 iodobenzene 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 75-63-8 Bromotrifluoromethane 
• 3111-52-2 potassium thiophenolate 
• 372-64-5 Bis(trifluoromethyl)disulfid 

Downstream Products

• 426-58-4 (trifluoromethylsulfonyl)benzene 
• 366-96-1 4-trifluoromethylsulfanyl-m-phenylenediamine 
• 22172-65-2 3-phenyl-5-trifluoromethylsulfanyl-benzo[c]isoxazole 
• 703-18-4 phenyl trifluoromethyl sulfoxide 
• 87996-58-5 trifluoromethylthio-4 fluoro-4' benzophenone 
• 701-65-5 (trichloromethylthio)benzene 
• 16936-63-3 Tribrommethyl-phenyl-sulfid 
• 70350-12-8 difluoro(phenyl)(trifluoromethyl)-λ⁴-sulfane 
• 144434-16-2 Phenyl-(2,2,2-trifluoro-1-furan-2-yl-ethyl)-amine 
• 191084-66-9 phenyl[2-(2-phenyl-1,1,1-trifluoroethyl)] amine 

Relevant academic research and scientific papers

New stable reagents for the nucleophilic trifluoromethylation. Part 4: Trifluoromethylation of disulfides and diselenides with hemiaminals of trifluoroacetaldehyde

Hemiaminals of fluoral and derivatives have been previously described as efficient new reagents for the nucleophilic trifluoromethylation of carbonyl compounds. Their use has been extended to the synthesis of trifluoromethyl sulfides and selenides from di

A New and Efficient Method for the Synthesis of Trifluoromethylthio- and Selenoethers

(Equation presented) A new atom-economic procedure for preparation of trifluoromethyl thio- and selenoethers is reported, wherein both halves of aryl and alkyl disulfides and diselenides are able to be utilized with high efficiency.

Nucleophilic perfluoroalkylation of diaryldisulfides with perfluorocarboxylate salts

A new industrial and economical route to trifluoromethyl aryl sufides by thermal decarboxylation of trifluoroacetate salts has been recently developed. The possibility of generalising this reaction of "trifluorodecarboxylation" to RfCO2K (Rf: CCl3, CF2Cl, CF3CF2, CF3CF2CF2) in order to synthesise RfSAr has been studied. Thus, the reaction was effective with RfCO2K (Rf=CCl3, CF3CF2) and a new route to aryl pentafluoroethyl sufides CF3CF2SAr has been briefly exemplified.

Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides

The first C?SCF3/SeCF3 cross-coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF3 or Me4NSeCF3, and organohalides as substrates are reported. The new methodology enables a one-stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers with a broad substrate scope (>60 examples with up to 97 % isolated yield). The method is scalable, and its robustness is evidenced by the late-stage functionalization of various bioactive molecules, which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio- and selenoethers for pharmaceutical and agrochemical research and development.

Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF3

Herein, we report an indirect trifluoromethylthiolation of sodium arylsulfinates. This transition-metal-free reaction significantly provides an environmentally friendly and practical synthetic method for aryl trifluoromethyl thioethers using commercial Ruppert-Prakash reagent TMSCF3. This approach is also a potential alternative to the current industrial production method owing to facile substrates, excellent functional group compatibility, and operational simplicity.

Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF3+, CF3?, and CF3-Reactivity

Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF3+OTf-) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from thianthrene and triflic anhydride. We demonstrate the use of TT-CF3+OTf- in electrophilic, radical, and nucleophilic trifluoromethylation reactions.

The First Organosilver(III) Fluoride, [PPh4][(CF3)3AgF]

Organosilver(III) fluoride complexes have been assigned a key role in different fluorination processes. To the best of our knowledge, however, none of them seem to have been isolated or even detected thus far. Here we report on the successful synthesis of the trifluoromethyl derivative [PPh4][(CF3)3AgF], which has been isolated in high yield. The thermodynamic stability of the Ag?F bond is shown by calculation and demonstrated by multistage mass spectrometry (MSn) under collision-induced dissociation (CID) conditions. Nevertheless, the substantial elongation found in the Ag?F bond (X-ray) is correlated with a marked nucleophilic character of the terminal F ligand. This Ag?F bond is, in fact, quite reactive: it suffers hydrolysis and is also solvolyzed by thiols.

Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3

An efficient method for trifluoromethylthiolation of arenediazonium salts has been developed in mild conditions with a stable and convenient AgSCF3. It provides a straightforward and convenient way for the synthesis of trifluoromethylthiolated compound from diazonium salts in moderate to good yields.

Ortho-lithiation reaction of aryl triflones

The ortho-lithiation of substituted arenes is a powerful methodology to synthesize ortho-substituted arenes. While a wide variety of directed metalation groups (DMGs) have been reported, trifluoromethyl sulfone has never been used. We disclose the first example of ortho-lithiation of aryl triflones. We found that the trifluoromethyl sulfonyl group is not only an important structural motif in biologically active molecules and specialty materials, but also an excellent DMG moiety for ortho-metalation reactions. The use of a base that causes steric hindrance, LTMP, is the key for successful transformation to furnish a variety of ortho-substituted aryl triflones in good yields. Further functionalization of resulting ortho-substituted aryl triflones was demonstrated by metal-catalyzed coupling reactions.

Synthesis of Chloro(phenyl)trifluoromethyliodane and Catalyst-Free Electrophilic Trifluoromethylations

The present work deals with a challenge in the synthesis of aryltrifluoromethyliodanes (ArICF3X) and develops a direct route to PhICF3Cl via a simple ligand-exchange reaction of PhI(OCOCF3)2, Me3SiCF3, and NaCl for the first time. The I-Cl bond length in PhICF3Cl supports its iodonium character, which enables an enhanced CF3-transfer capability in electrophilic S-, O-, N-, and C-trifluoromethylations as well as in catalyst-free trifluoromethylation-cyclizations of arylisonitriles.