29540-81-6

Usage

Uses

Used in Pharmaceutical Industry:
1-(TRIFLUOROMETHANESULFONYL)IMIDAZOLE is used as a building block for the synthesis of complex organic molecules, particularly in the development of new pharmaceutical compounds. Its unique reactivity allows for the creation of diverse molecular structures, contributing to the advancement of drug discovery and design.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(TRIFLUOROMETHANESULFONYL)IMIDAZOLE serves as a key intermediate in the synthesis of various bioactive compounds. Its application aids in the development of innovative agrochemicals that can address challenges in crop protection and pest management.
Used as a Precursor in Active Pharmaceutical Ingredients Production:
1-(TRIFLUOROMETHANESULFONYL)IMIDAZOLE is utilized as a precursor in the production of active pharmaceutical ingredients. Its role in the synthesis process is crucial for generating the desired bioactive molecules, which are then used in the formulation of medications to treat various diseases and conditions.
Used in Organic Synthesis:
As a building block in organic synthesis, 1-(TRIFLUOROMETHANESULFONYL)IMIDAZOLE is employed for the creation of a wide range of organic compounds. Its electron-withdrawing properties facilitate various chemical reactions, making it a valuable component in the synthesis of molecules with specific functional groups and properties.

InChI:InChI=1/C6H5FIN/c7-5-3-4(8)1-2-6(5)9/h1-3H,9H2

Upstream product

• 288-32-4 1H-imidazole 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 421-83-0 trifluoromethane sulfonyl chloride 

Downstream Products

• 41381-28-6 3,5-dicyclopropylphenyl trifluoromethanesulfonate 
• 41381-29-7 <3,5-Bis(1-methylcyclopropyl)phenyl>trifluormethansulfonat 
• 109057-09-2 N-(trifluoromethylsulfonyl)pyrrole 
• 69025-95-2 (+/-)-6,6aβ,7,8,10,10aα-hexahydro-6,6-dimethyl-3-(1-methyl-4-phenylbutoxy)spiro<9H-dibenzopyran-9,2'-<1,3>dioxolan>-1-yl trifluoromethanesulfonic acid ester 
• 29540-83-8 p-tolyl triflate 
• 17763-67-6 Phenyl triflate 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 17763-80-3 para-nitrophenyl triflate 

Relevant academic research and scientific papers

TRIFLAZOLES AND METHODS OF MAKING THE SAME

Methods for producing triflazoles or related derivatives thereof, and the resulting products are provided. For example, triflazoles can be prepared by reaction of trifluoromethanesulfonyl fluoride with an azole or azolate salt. Yields up to 78% are obtained. Triflazoles can be prepared by the reaction of a trifluoromethanesulfonyl fluoride with an N-silylazole in the presence of a basic catalyst. Yields up to 97% are obtained.

Highly efficient preparation of amides from aminium carboxylates using N-(p-toluenesulfonyl) imidazole

Treatment of aminium carboxylates with N-(p-toluenesulfonyl)imidazole in the presence of triethylamine in DMF at 100 °C afforded the corresponding amides in good to excellent yields. N-(p-Toluenesulfonyl)imidazole proved to be a highly efficient coupling reagent for the preparation of numerous structurally diverse primary, secondary and tertiary amides.

Reaction of triflyl-imidazole with aldoximes: Facile synthesis of nitriles and formation of novel aldoxime-bis(N-triflyl)-imidazole adducts

The synthetic utility of N-triflylimidazole as an in situ reagent for facile, high yielding, synthesis of various aliphatic, aromatic, and heteroaromatic nitriles from the corresponding aldoximes has been demonstrated. With benzaldoximes, in the presence of certain substitutents (2-F; 2-OMe; 3-CF3; 2-Me-5-F) a different course of reaction was observed, leading instead to novel 1:1 aldoxime-bis(N-triflyl)imidazole covalent adducts, in which the aldoxime oxygen atom is bonded to the imidazole C-2 ring carbon. For these aldoximes, conversion to nitrile could be effected by reaction with Tf2O in the absence of imidazole. The molecular structure of the adduct formed from 2-methyl-5-fluoro-benzaldoxime was confirmed by X-ray analysis. Plausible mechanisms for the formation of 1:1 covalent adducts have been considered. Various attempts to isolate such adducts via the reaction of an authentic sample of bis(N-triflyl)imidazolium trifate with aldoxime were unsuccessful. Remarkably, whereas isolated benzaldoxime adducts undergo deprotonation/methylation with NaH/MeI, an authentic sample of bis(N-triflyl)imidazolium triflate did not undergo H/Me exchange under these conditions. These transformations are discussed.