719-98-2 | N-(trifluoromethylthio)phthalimide

CAS:719-98-2 | N-(trifluoromethylthio)phthalimide ,Description

N-(Trifluoromethylthio)phthalimide (TFMP) is a fluorinated sulfur-containing derivative of phthalimide, which is an important synthetic building block used in organic synthesis and drug discovery. TFMP has a wide range of applications in both scientific research and industrial production. It can be used in the synthesis of several compounds, such as insecticides, herbicides, and pharmaceuticals, and has been found to have potential applications in the areas of biochemistry, physiology, and pharmacology. 
 

Scientific Research Applications

Synthesis and Organic Chemistry

N-(trifluoromethylthio)phthalimide is a valuable reagent in organic synthesis, offering a safe and efficient method for trifluoromethylthiolation. It has been used for the direct trifluoromethylthiolation of boronic acids and alkynes under copper catalysis, demonstrating its versatility and functionality in creating biologically active agents and industrial pharmaceuticals (Pluta, Nikolaienko, & Rueping, 2014). Further, its use in the trifluoromethylthiolation of aryl and vinyl boronic acids highlights its high yield and applicability in producing trifluoromethylthiolated arenes and alkenes (Kang, Xu, & Shen, 2014).

Catalysis and Enantioselective Reactions

In catalysis, this compound facilitates enantioselective trifluoromethylthiolation, especially of oxindoles. This process yields optically active products with high enantioselectivities, emphasizing its significance in producing compounds with specific stereochemistry (Rueping, Liu, Bootwicha, Pluta, & Merkens, 2014).

Medicinal and Agrochemical Applications

N-(trifluoromethylthio)phthalimide is crucial in preparing trifluoromethanesulfenamides and unsymmetrical disulfides. These compounds are noteworthy for their potential in medicinal and agrochemical applications, thanks to their remarkable properties (Pluta & Rueping, 2014).

Continuous Flow Synthesis

The compound is also central in the continuous flow synthesis of α-trifluoromethylthiolated esters and amides from carboxylic acids, demonstrating a novel and efficient approach in organic synthesis (Franco, Meninno, Lattanzi, Puglisi, & Benaglia, 2021) .

Materials Science

In materials science, N-(trifluoromethylthio)phthalimide has been involved in the development of phthalimide–thiophene copolymers, influencing the properties of materials used in electronics like OFETs, LEFETs, and NIR PLEDs (Steckler, Lee, Chen, Fenwick, Andersson, Cacialli, & Sirringhaus, 2014).

Environmental Applications

Furthermore, phthalimide-modified cellulose nanofibers, utilizing compounds like N-(trifluoromethylthio)phthalimide, have shown promise in applications like CO2 adsorption, demonstrating the compound's utility in addressing environmental challenges (Sepahvand, Jonoobi, Ashori, Gauvin, Brouwers, Oksman, & Yu, 2020).

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