352-68-1

Usage

Uses

Used in Pharmaceutical Industry:
4-(TRIFLUOROMETHYLTHIO)TOLUENE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures that are essential in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(TRIFLUOROMETHYLTHIO)TOLUENE is employed as an intermediate in the production of agrochemicals, playing a crucial role in the development of compounds that protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
4-(TRIFLUOROMETHYLTHIO)TOLUENE is used as a reagent in organic synthesis, facilitating specific chemical reactions that are vital for the creation of a wide range of organic compounds.
Used as a Solvent in Organic Reactions:
4-(TRIFLUOROMETHYLTHIO)TOLUENE also serves as a solvent for various organic reactions, providing a medium that supports the desired chemical processes and improves the efficiency of these reactions.
Safety Precautions:
Given its flammable nature and potential harmful effects if inhaled, ingested, or absorbed through the skin, 4-(TRIFLUOROMETHYLTHIO)TOLUENE requires careful handling and proper safety measures to ensure the well-being of those who work with it.

InChI:InChI=1/C8H7F3S/c1-6-2-4-7(5-3-6)12-8(9,10)11/h2-5H,1H3

Upstream product

• 2976-38-7 p-tolyltrichloromethylsulfide 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 696-61-7 4-tolylmagnesium chloride 
• 75-63-8 Bromotrifluoromethane 
• 26330-85-8 4-Methyl-benzenethiol anion 
• 31367-69-8 potassium p-tolylthiolate 
• 33453-95-1 lithium p-toluenethiolate 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 106-38-7 para-bromotoluene 
• 106-45-6 para-thiocresol 
• 2314-97-8 iodotrifluoromethane 
• 42530-92-7 trifluoromethyl-sulfenyl acetate 
• 108-88-3 toluene 
• 55642-42-7 bis(trifluoromethyl)tellurium 

Downstream Products

• 383-10-8 1-methyl-4-(trifluoromethylsulfonyl)benzene 
• 393-99-7 (4-methyl-2-nitro-phenyl)-trifluoromethyl sulfoxide 
• 363-98-4 (4-methyl-2-nitro-phenyl)-trifluoromethyl sulfone 
• 2189-43-7 p-tolyl trifluoromethyl sulfoxide 
• 2192-27-0 (3-Nitro-4-methyl-phenyl)-trifluormethyl-sulfon 
• 70124-90-2 2-(4-((trifluoromethyl)thio)phenyl)acetonitrile 
• 1933-61-5 <4-Carboxy-3-nitro-phenyl>-trifluormethyl-sulfon 
• 243977-23-3 2-(4-((trifluoromethyl)thio)phenyl)acetic acid 
• 1099597-82-6 2-(4-(trifluoromethylsulfonyl)phenyl)acetic acid 
• 1948-09-0 (2-Amino-4-methyl-phenyl)-trifluormethyl-sulfoxid 
• 21101-63-3 4-(trifluoromethylthio)benzyl bromide 
• 118754-62-4 2,3,5,6-tetrachloro-4-trifluoromethylthiotoluene 
• 75070-85-8 rhodium hydrido (PEt₃)3 complex 
• 21101-67-7 3-(4-trifluoromethylsulfanyl-phenyl)-acrylic acid 

Relevant academic research and scientific papers

Direct Trifluoromethylthiolation of Aryl Halides using Methyl Fluorosulfonyldifluoroacetate and Sulfur

In the presence of S8 and copper(I) iodide, methyl fluorosulfonyldifluoroacetate 1 reacts with aryl halides 2 in hexamethylphosphoramide (HMPA) or N-methylpyrrolidinone (NMP) at 100-110 deg C to give the corresponding trifluoromethylthiolated derivatives 3 in good yields.

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.

Synthesis of Symmetrical Thiosulfonates via Cu(OTf)2-Catalyzed Reductive Homocoupling of Arenesulfonyl Chlorides

A variety of symmetrical thiosulfonates are synthesized via Cu-catalyzed reductive homocoupling of aryl sulfonyl chlorides. This protocol uses organic amine acting as a mild reductant and low-cost copper as an effective catalyst. Such a reductive coupling process features a broad substrate scope and good functional group tolerance. Related thiosulfonate products can also be converted into diverse functional molecules.

Trifluoromethyl Sulfoxides: Reagents for Metal-Free C?H Trifluoromethylthiolation

Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C?H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism.

Perfluoroalkylation of Thiosulfonates: Synthesis of Perfluoroalkyl Sulfides

A practical synthesis of perfluoroalkyl sulfides is described. The method employs stable and readily accessible thiosulfonates as new electrophiles with commercial nucleophilic perfluoroalkylating reagents. The mild reaction conditions allow access to a wide variety of both aryl- and alkyl-substituted perfluoroalkyl sulfides amenable to pharmaceutical development. Furthermore, the reaction operation is straightforward, odorless, does not produce toxic wastes, and, therefore should appeal to practitioners in industrial-scale productions.

Visible-Light-Mediated Synthesis of Trifluoromethylthiolated Arenes

The visible-light-mediated synthesis of trifluoromethylthiolated arenes in the presence of ruthenium-based photocatayst under mild reaction conditions is reported. The trifluoromethylthiolated arenes are obtained using the shelf-stable reagent trifluoromethyl toluenethiosulfonate at room temperature. The reaction proceeds selectively and does not require the presence of any additive. A mechanism is proposed based on the obtained results of EPR as well as luminescence.

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.

Tf2O-Promoted Trifluoromethythiolation of Various Arenes Using NaSO2CF3

A sulfonic anhydride-promoted direct trifluoromethylthiolation using NaSO2CF3 has been developed. The simple and practical strategy enabled the direct introduction of SCF3 moiety into unexplored arene scaffolds under reductant- and metal-free condition at room temperature. (Figure presented.).

Metal-free trifluoromethylthiolation of arenediazonium salts with Me4NSCF3

A metal-free entry to the pharmaceutically meaningful substrate class of trifluoromethyl thioethers has been developed starting from widely available arenediazonium salts and commercially available Me4N+SCF3?. This reaction proceeds within one hour at 0 °C and is applicable to a wide range of functionalized substrates.

Diversification of Trifluoromethylthiolation of Aromatic Molecules with Derivatives of Trifluoromethanesulfenamide

Trifluoromethylthiolation of aromatic compounds with different electrophilic reagents of the type ArNHSCF3 was studied in the presence of triflic acid as an activator. The effect of the reagent structure on the reactivity was studied with three different reagents: PhNHSCF3 (H/SCF3, 1a), 4-ClC6H4NHSCF3 (Cl/SCF3, 1b) and C6F5NHSCF3 (F5/SCF3, 1c). p-Chloro substituted reagent 1b was more stable than the unsubstituted 1a and was the most effective because it could not react by trifluoromethylthiolation of itself. This reaction was the most important side reaction of 1a. The pentafluoro derivative 1c was less reactive. Solvent played an important role in the transformation and, depending on the substrate, dichloromethane, hexane or trifluoroacetic acid gave the best yield of various trifluoromethylthiolated aromatic molecules (63–98 %).