88489-60-5

Usage

Uses

Used in Pharmaceutical and Agricultural Chemical Industries:
METHYL 4-TRIFLUOROMETHYLTHIO BENZOATE is used as an intermediate in the synthesis of various pharmaceuticals and agricultural chemicals, leveraging its unique reactivity and properties to contribute to the development of new and effective products.
Used in Flavor and Fragrance Industry:
In the production of perfumes and other consumer products, METHYL 4-TRIFLUOROMETHYLTHIO BENZOATE is used as a flavor and fragrance ingredient, adding unique scents and enhancing the sensory experience of these products.

InChI:InChI=1/C9H7F3O2S/c1-14-8(13)6-2-4-7(5-3-6)15-9(10,11)12/h2-5H,1H3

Upstream product

• 333-47-1 1-bromo-4-(trifluoromethyl)thiobenzene 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 67-56-1 methanol 
• 330-14-3 4-(trifluoromethylthio)benzoyl chloride 
• 330-17-6 4-(trifluoromethylthio)benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 1413732-47-4 (2,2'-bipyride-kN₁,kN₁')(1,1,1-trifluoromethanethiolato-kS)-copper 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 619-44-3 methyl 4-iodobenzoate 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 1879-22-7 4-(methoxycarbonyl)phenyl thiocyanate 
• 2923-16-2 potassium trifluoroacetate 
• 1640084-14-5 (((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane) 

Downstream Products

• 330-17-6 4-(trifluoromethylthio)benzoic acid 
• 88489-67-2 methyl 4-((trifluoromethyl)sulfonyl)benzoate 
• 312-22-1 4-((trifluoromethyl)sulfonyl)benzoic acid 

Relevant academic research and scientific papers

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.

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.

Metal-Free Trifluoromethylthiolation of Arylazo Sulfones

A visible-light-driven protocol for the synthesis of aryl trifluoromethyl thioethers under photocatalyst- and metal-free conditions has been pursued. The procedure exploits the peculiar properties of arylazo sulfones (having electron-rich or electron-poor substituents on the (hetero)aromatic ring) as photochemical precursors of aryl radicals and S-trifluoromethyl arylsulfonothioates as easy-to-handle trifluoromethylthiolating agents.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

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.

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.

Difluoro(aryl)(perfluoroalkyl)-λ4-sulfanes and Selanes: Missing Links of Trichloroisocyanuric Acid/Potassium Fluoride Chemistry

The TCICA/KF approach to oxidative fluorination of heteroatoms has emerged as a surprisingly simple, safe, and versatile surrogate to classically challenging fluorination reactions. Although polyfluorination (or chlorofluorination) of diaryl disulfides, diaryl diselenides, diaryl ditellurides, aryl iodides, and aryl(perfluoroalkyl)tellanes has been described, the application of this TCICA/KF methodology to aryl(perfluoroalkyl)sulfanes and selanes remains an area of unexplored chemical space. Accordingly, to address the “missing links” in the developing series of chalcogen-based substrate reactivity, we report mild syntheses of metastable difluoro(aryl)(perfluoroalkyl)-λ4-sulfanes and selanes. As only limited examples of these species exist in the current literature (accessible only by using F2 or XeF2/HF), we have carried out detailed structural analyses, primarily using NMR and SC-XRD data. In addition, we investigate the effect of the perfluoroalkyl chain on the outcome of oxidative fluorination, and, finally, we provide preliminary evidence that difluoro(aryl)(trifluoro-methyl)-λ4-sulfanes may act as fluorinating reagents.

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.

Cu-mediated oxidative trifluoromethylthiolation of arylboronic acids with (bpy)CuSCF3

An efficient trifluoromethylthiolation reaction of arylboronic acids with (bpy)CuSCF3in the presence of oxygen at room temperature is described. This method produces a variety of aryl trifluoromethylthioether derivatives in good to high yield. The mechanism of this trifluoromethylthiolation is discussed as well.

O-Trifluoromethylation of Phenols: Access to Aryl Trifluoromethyl Ethers by O-Carboxydifluoromethylation and Decarboxylative Fluorination

A new strategy for the synthesis of aryl trifluoromethyl ethers (ArOCF3) by combining O-carboxydifluoromethylation of phenols and subsequent decarboxylative fluorination is reported. This protocol allows easy construction of functionalized trifluoromethoxybenzenes and trifluoromethylthiolated arenes (ArSCF3) in moderate to good yields. Moreover, it utilizes accessible and inexpensive reagents sodium bromodifluoroacetate and SelectFluor II and, thus, is practical for O-trifluoromethylation of phenols. The potential application of this method is demonstrated with the preparation of a plant-growth regulator, Flurprimidol.