199188-29-9

Usage

Uses

Used in Green Synthetic Preparation:
2-(TRIFLUOROMETHYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent in the green synthetic preparation of N-aryl sulfonamides. It facilitates the reaction under mild conditions, which is beneficial for the environment and the overall sustainability of the process.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(TRIFLUOROMETHYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a key intermediate in the synthesis of various drugs, particularly those with anti-inflammatory, analgesic, and antipyretic properties. Its unique reactivity allows for the efficient production of these therapeutic compounds.
Used in Chemical Research:
2-(TRIFLUOROMETHYL)PHENYL TRIFLUOROMETHANESULFONATE is also utilized in chemical research as a versatile reagent for the functionalization of various organic substrates. Its ability to participate in a wide range of reactions, such as substitution, addition, and elimination, makes it a valuable tool for the development of new chemical entities and materials.
Used in Material Science:
In the field of material science, 2-(TRIFLUOROMETHYL)PHENYL TRIFLUOROMETHANESULFONATE is employed in the synthesis of novel polymers and materials with specific properties, such as enhanced thermal stability, chemical resistance, and mechanical strength. Its unique structure contributes to the development of advanced materials for various applications, including aerospace, electronics, and automotive industries.
Overall, 2-(TRIFLUOROMETHYL)PHENYL TRIFLUOROMETHANESULFONATE is a versatile and valuable compound with a wide range of applications across different industries, including pharmaceuticals, green synthetic chemistry, chemical research, and material science. Its unique properties and reactivity make it an essential component in the development of new drugs, materials, and processes.

InChI:InChI=1/C8H4F6O3S/c9-7(10,11)5-3-1-2-4-6(5)17-18(15,16)8(12,13)14/h1-4H

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 444-30-4 2-(trifluoromethyl)phenol 
• 533-58-4 2-Iodophenol 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 129112-26-1 2-iodophenyltrifluoromethanesulfonic acid 

Downstream Products

• 1043912-29-3 2-trifluoromethyl-6-trifluoromethanesulphonylphenol 
• 1334500-64-9 diisopropyl 1-[2-(trifluromethyl)phenyl]-hydrazine-1,2-dicarboxylate 
• 191867-93-3 1-phenyl-1-(2-trifluoromethylphenyl)ethylene 

Relevant academic research and scientific papers

Suzuki-miyaura cross-coupling reactions in flow: Multistep synthesis enabled by a microfluidic extraction

Continuous success: A continuous-flow Suzuki-Miyaura cross-coupling reaction starting from phenols was made possible through use of an efficient microfluidic extraction operation and a packed-bed reactor. Various biaryls were obtained in excellent yield (

Decoupling deprotonation from metalation: Thia-fries rearrangement

(Chemical Equation Presented) Label-enabled: Studies with 2H-, 18O-, and 34S-labeled aryl triflates show that lithium diisopropylamide-mediated thia-Fries rearrangement proceeds through an irreversible ortho deprotonation (see scheme; DIPA = diisopropylamine, LDA = lithium diisopropylamide). In contrast, ortho metalation results exclusively in the generation of a benzyne.

On the preparation of ortho-trifluoromethyl phenyl triflate

In contrast to an earlier report advocating a copper-mediated trifluoromethylation of ortho-iodophenyl triflate, ortho-trifluoromethyl phenyl triflate may be prepared simply by reacting the corresponding phenol with triflic anhydride in the presence of a

First synthesis of ortho-trifluoromethylated aryl triflates

An efficient method for the preparation of trifluoromethylated aryl triflates (trifluoromethanesulfonates) has been developed. Treatment of 2-iodophenol with trifluoromethanesulfonic anhydride in the presence of triethylamine gives triflate 3. Then, reaction of compound 3 with FSO2CF2CO2Me and CuI in DMF-HMPA affords trifluoromethylated aryl triflate 2. This reaction sequence is also successful for meta- and para-trifluoromethylated aryl triflates. Based on this methodology, the trifluoromethylated aryl triflate 11, a key intermediate for the preparation of the conformationally restricted retinoid 8 containing a trifluoromethyl group, has been synthesized. The cross-coupling of aryl triflate 11 with vinylstannane 17 under palladium catalysis provides compound 18, the methyl ester of retinoid 8, in moderate yield.