56773-33-2

Usage

Uses

Used in Organic Synthesis:
3'-(Trifluoromethylthio)acetophenone is used as a key intermediate in the synthesis of various organic compounds. Its unique trifluoromethylthio and acetophenone structures make it a valuable building block for creating complex molecules with potential applications in pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3'-(Trifluoromethylthio)acetophenone is used as a starting material for the development of new drugs. Its chemical properties allow for the creation of novel molecular structures with potential therapeutic effects. 3'-(TRIFLUOROMETHYLTHIO)ACETOPHENONE's reactivity and stability make it suitable for use in the synthesis of a wide range of pharmaceutical agents.
Used in Agrochemical Industry:
3'-(Trifluoromethylthio)acetophenone is also used in the agrochemical industry as a precursor for the synthesis of new pesticides and herbicides. Its unique chemical structure can be utilized to create compounds with improved efficacy and selectivity, leading to more effective crop protection products.
Used in Materials Science:
In materials science, 3'-(Trifluoromethylthio)acetophenone is used as a component in the development of advanced materials with specific properties. Its incorporation into polymers and other materials can result in new materials with enhanced properties, such as improved thermal stability, chemical resistance, or electrical conductivity.

InChI:InChI=1/C9H7F3OS/c1-6(13)7-3-2-4-8(5-7)14-9(10,11)12/h2-5H,1H3

Upstream product

• 946-65-6 3-(trifluoromethylthio)benzoic acid 
• 917-54-4 methyllithium 
• 14452-30-3 3'-iodoacetophenone 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 99-03-6 1-(3-aminophenyl)ethanone 
• 14428-55-8 3-acetylphenyl thiocyanate 
• 2923-16-2 potassium trifluoroacetate 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 138313-22-1 3-acetylphenyl trifluoromethanesulfonate 

Downstream Products

• 56773-34-3 m-Trifluormethylthio-α-bromacetophenon 
• 1100768-13-5 N-(4-carbamimidoyl-phenyl)-N'-[1-(3-trifluoromethanesulfonyl-phenyl)-ethyl]-malonamide trifluoroacetate 
• 1100768-10-2 N-(4-carbamimidoyl-phenyl)-N'-[(S)-1-(3-trifluoromethanesulfonyl-phenyl)-ethyl]-malonamide trifluoroacetate 
• 1100767-99-4 N-(4-carbamimidoyl-phenyl)-N'-[1-(3-trifluoromethanesulfinyl-phenyl)-ethyl]-malonamide trifluoroacetate 
• 1100768-11-3 1-(3-trifluoromethanesulfonyl-phenyl)-ethylamine 
• 1100768-02-2 1-(3-trifluoromethanesulfinyl-phenyl)-ethylamine 
• 765917-10-0 (3-trifluoromethylsulfanylphenyl)-oxoacetaldehyde 
• 1100768-00-0 1-(3-trifluoromethanesulfinyl-phenyl)-ethanone 
• 1100768-01-1 1-(3-trifluoromethanesulfonyl-phenyl)-ethanone 

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.

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.

Copper-Mediated Oxidative Trifluoromethylthiolation of Potassium Aryltrifluoroborates with Elemental Sulfur and Ruppert-Prakash Reagent

A facile procedure for the copper-mediated oxidative trifluoromethylthiolation of potassium aryl- and heteroaryltrifluoroborates with Ruppert-Prakash reagent and elemental sulfur is presented. Aryl trifluoromethyl thioethers can be prepared in good to mod

Nickel-catalyzed trifluoromethylthiolation of Csp2-O bonds

While nickel catalysts have previously been shown to activate even the least reactive Csp2-O bonds, i.e. aryl ethers, in the context of C-C bond formation, little is known about the reactivity limits and molecular requirements for the introduction of valuable functional groups under homogeneous nickel catalysis. We identified that due to the high reactivity of Ni-catalysts, they are also prone to react with existing or installed functional groups, which ultimately causes catalyst deactivation. The scope of the Ni-catalyzed coupling protocol will therefore be dictated by the reactivity of the functional groups towards the catalyst. Herein, we showed that the application of computational tools allowed the identification of matching functional groups in terms of suitable leaving groups and tolerated functional groups. This allowed for the development of the first efficient protocol to trifluoromethylthiolate Csp2-O bonds, giving the mild and operationally simple C-SCF3 coupling of a range of aryl, vinyl triflates and nonaflates. The novel methodology was also applied to biologically active and pharmaceutical relevant targets, showcasing its robustness and wide applicability.

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.

Iron-Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers

Nucleophilic CF3 has been generated by decarboxylation of potassium trifluoroacetate, arguably the most easy-to-handle, inexpensive, and sustainable source of trifluoromethyl groups. Simple iron(II) chloride catalyzes the decarboxylation as well as a subsequent trifluoromethylation of organothiocyanates, resulting in a straightforward synthesis of trifluoromethyl thioethers. The KCN byproduct is absorbed by iron(II) with formation of nontoxic potassium hexacyanoferrate. An analogous trifluoromethylation of aldehydes with trifluoroacetate underlines the synthetic potential of such iron-catalyzed decarboxylative trifluoromethylations.

Sandmeyer trifluoromethylthiolation of arenediazonium salts with sodium thiocyanate and Ruppert-Prakash reagent

In the presence of copper thiocyanate, sodium thiocyanate and the inexpensive, easy-to-use trifluoromethylating reagent Me3Si-CF 3, diazonium salts are smoothly converted into the corresponding aryl trifluoromethyl thioethers. Combin

Synthesis and discovery of 2,3-dihydro-3,8-diphenylbenzo[1,4]oxazines as a novel class of potent cholesteryl ester transfer protein inhibitors

2,3-Dihydro-3,8-diphenylbenzo[1,4]oxazines were identified as a new class of potent cholesteryl ester transfer protein inhibitors. The most potent compound 6a (IC50 = 26 nM) possessed a favorable pharmacokinetic profile with good oral bioavailability in rat (F = 53%) and long human liver microsome stability (t1/2 = 62 min). It increased HDL-C in human CETP transgenic mice and high-fat fed hamsters. The structure and activity relationship of this series will be described in this Letter.