957188-75-9

Basic information

• Product Name: [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ³-bromane
• Synonyms: [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ³-bromane
• CAS NO: 957188-75-9
• Molecular Weight: 372.086
• Mol File: 957188-75-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ³-bromane(CAS DataBase Reference)
• NIST Chemistry Reference: [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ³-bromane(957188-75-9)
• EPA Substance Registry System: [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ³-bromane(957188-75-9)

Safety Data

• Hazardous Substances Data: 957188-75-9(Hazardous Substances Data)

Upstream product

• 421-85-2 Trifluoromethanesulfonamide 
• 206753-28-8 difluoro[4-(trifluoromethyl)phenyl]-λ³-bromane 
• 1335436-87-7 [p-(trifluoromethyl)phenyl](diacetoxy)-λ3-bromane 
• 312-75-4 trimethyl(4-trifluoromethylphenyl)silane 

Downstream Products

• 957188-84-0 2-phenyl-N-[(trifluoromethyl)sulfonyl]aziridine 
• 957188-85-1 2-(4-chlorophenyl)-N-[(trifluoromethyl)sulfonyl]aziridine 
• 957188-81-7 cis-2,3-diphenyl-N-[(trifluoromethyl)sulfonyl]aziridine 
• 1099795-94-4 dimethyl(benzyl)ammonium (trifluoromethanesulfonyl)imide 
• 1133467-90-9 [N-(trifluoromethanesulfonyl)imino](2-carbamoyl-4-methylphenyl)-λ3-iodane 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 1133467-75-0 [N-(trifluoromethanesulfonyl)imino](4-chlorophenyl)-λ3-iodane 
• 1133467-73-8 [N-(trifluoromethanesulfonyl)imino](4-methylphenyl)-λ3-iodane 
• 1133467-74-9 [N-(trifluoromethanesulfonyl)imino](4-methoxyphenyl)-λ3-iodane 
• 1133467-77-2 [N-(trifluoromethanesulfonyl)imino][4-(trifluoromethyl)phenyl]-λ3-iodane 
• 1133467-72-7 [N-(trifluoromethanesulfonyl)imino](2-methylphenyl)-λ3-iodane 
• 1133467-76-1 [N-(trifluoromethanesulfonyl)imino](4-bromophenyl)-λ3-iodane 
• 1133467-78-3 [N-(trifluoromethanesulfonyl)imino](4-cyanophenyl)-λ3-iodane 
• 1133467-89-6 [N-(trifluoromethanesulfonyl)imino](2-carbamoylphenyl)-λ3-iodane 

Relevant articles and documents

Benchtop-Stabssle Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- And Moisture-Stable λ3-Bromanes

We present the first synthesis of air/moisture-stable λ3-bromanes (9and10) by using a cyclic 1,2-benzbromoxol-3-one (BBX) strategy. X-ray crystallography and NMR and IR spectroscopy ofN-triflylimino-λ3-bromane (12) revealed that the bromine(III) center is effectively stabilized by intramolecular R-Br-O hypervalent bonding. This strategy enables the synthesis of a variety of air-, moisture-, and benchtop-stable Br-hydroxy, -acetoxy, -alkynyl, -aryl, and bis[(trifluoromethyl)sulfonyl]methylide λ3-bromane derivatives.

Highly regioselective amination of unactivated alkanes by hypervalent sulfonylimino-δ3-bromane

Amination of alkanes has generally required metal catalysts and/or high temperatures. Here we report that simple exposure of a broad range of alkanes to N-triflylimino-δ3-bromane 1 at ambient temperature results in C-H insertion of the nitrogen functionality to afford triflyl-substituted amines in moderate to high yields. Marked selectivity for tertiary over secondary C-H bonds was observed; primary (methyl) C-H bonds were inert. Addition of hexafluoroisopropanol to inhibit decomposition of 1 dramatically improved the C-H amination efficiencies. Second-order kinetics, activation parameters (negative activation entropy), deuterium isotope effects, and theoretical calculations suggest a concerted asynchronous bimolecular transition state for the metal-free C-H amination event.

Direct transfer of the sulfonylimino group of imino-λ3- bromane to N-heterocycles and trialkylamines: Synthesis of N-iminoammonium ylides under metal-free conditions

(Chemical Equation Presented) Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-λ3-bromane at room temperature results in direct transfer of the sulfonylimino group to the nitrogen atoms and affords a vari