940-76-1

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C7H4F4S/c8-5-1-3-6(4-2-5)12-7(9,10)11/h1-4H

Upstream product

• 352-34-1 4-fluoro-1-iodobenzene 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 371-42-6 4-Fluorothiophenol 
• 98-08-8 α,α,α-trifluorotoluene 
• 911360-86-6 α,α-difluoro(4-fluorophenylthio)acetic acid 
• 1640084-14-5 (((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane) 
• 1765-93-1 4-fluoroboronic acid 
• 225916-39-2 2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 15223-20-8 1-methyl-4-{[(trifluoromethyl)sulfanyl]sulfonyl}benzene 
• 371-40-4 4-fluoroaniline 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 1413732-47-4 (2,2'-bipyride-kN₁,kN₁')(1,1,1-trifluoromethanethiolato-kS)-copper 
• 2924-02-9 1-fluoro-4-thiocyanatobenzene 
• 2923-16-2 potassium trifluoroacetate 

Downstream Products

• 944-30-9 p-fluorophenyl trifluoromethyl sulfone 
• 37552-84-4 methyl (4-((trifluoromethyl)sulfonyl)phenyl)sulfane 
• 834-02-6 2-fluoro-5-trifluoromethanesulfonyl-aniline 
• 656-83-7 (4-fluoro-3-nitro-phenyl)-trifluoromethyl sulfone 
• 942-39-2 1-fluoro-4-((trifluoromethyl)sulfinyl)benzene 
• 95970-30-2 C₈H₄F₇NO₂S₂ 
• 75070-85-8 rhodium hydrido (PEt₃)3 complex 

Relevant academic research and scientific papers

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.

Transition-Metal-Free ipso-Trifluoromethylthiolation of Lithium Aryl Boronates

A transition-metal-free direct trifluoromethylthiolation of the ipso-carbon of lithium aryl boronates with trifluoromethanesulfenate under mild conditions was described. In addition, late-stage site-selective C-H borylation/trifluoromethylation and C-Cl b

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.

Silver-catalyzed fluoroalkylation of thiols using fluoroalkanesulfinates

A practical sliver-catalyzed fluoroalkylation of aryl-, heteroaryl- and alkylthiols has been developed. The reaction has a good functional-group tolerance and excellent selectivity. A variety of stable and solid fluoroalkanesulfinates including di- and perfluoroalkanesulfinates can be employed. This methodology provides a straightforward and streamlined access to perfluoroalkylthiolated organic molecules. [Figure presented]

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.

Sandmeyer-Type Trifluoromethylthiolation and Trifluoromethylselenolation of (Hetero)Aromatic Amines Catalyzed by Copper

Aromatic and heteroaromatic diazonium salts were efficiently converted into the corresponding trifluoromethylthio- or selenoethers by reaction with Me4NSCF3 or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. These Sandmeyer-type reactions proceed within one hour at room temperature, are applicable to a wide range of functionalized molecules, and can optionally be combined with the diazotizations into one-pot protocols.

Trifluoromethylation of thiophenols and thiols with sodium trifluoromethanesulfinate and iodine pentoxide

A selective and facile trifluoromethylation process for a wide range of thiophenols and thiols under metal free conditions has been developed using two simple and safe solids, sodium trifluoro-methanesulfinate and iodine pentoxide, via the radical process.

Triphenylphosphine-Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for Trifluoromethylthiolation of Aryl Iodides

We report herein a practical method for taming Langlois' reagent CF3SO2Na to generate CuSCF3 by a triphenylphospine-mediated deoxygenative reduction process. This chemistry highlights a novel utilization of the inherent CF3S skeleton of Langlois' reagent as a CF3S feedstock under mild conditions. The CuSCF3 intermediate generated by this protocol can react with a wide array of supporting ligands to furnish several air-stable [LCu(SCF3)] complexes as valuable trifluoromethylthiolating agents. In addition, the CuSCF3 intermediate can be directly employed for the trifluoromethylthiolation of (hetero)aryl iodides with operational simplicity and atomic efficiency. Efficient synthesis! A low cost method for the generation of CuSCF3 by a triphenylphospine-mediated deoxygenative reduction of Langlois' reagent (CF3SO2Na) has been developed (see scheme). This method can be applied for the convenient synthesis of a wide array of ligated and air-stable CuSCF3 complexes. Additionally, the CuSCF3 complexes generated in situ by this protocol were found to trifluoromethylthiolate (hetero)aryl iodides with high efficiency.

S-Trifluoromethylation of Thiols by Hypervalent Iodine Reagents: A Joint Experimental and Computational Study

The radical trifluoromethylation of thiophenol in condensed phase applying reagent 1 (3,3-dimethyl-1-(trifluoromethyl)-1λ3,2-benziodoxol) has been examined by both theoretical and experimental methodologies. On the basis of ab initio molecular