166903-46-4

Basic information

• Product Name: 1-[hydroxy(tosyloxy)iodo]-1H,1H-perfluoroethane
• Synonyms: 1-[hydroxy(tosyloxy)iodo]-1H,1H-perfluoroethane
• CAS NO: 166903-46-4
• Molecular Weight: 398.142
• Mol File: 166903-46-4.mol

Chemical Properties

• CAS DataBase Reference: 1-[hydroxy(tosyloxy)iodo]-1H,1H-perfluoroethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[hydroxy(tosyloxy)iodo]-1H,1H-perfluoroethane(166903-46-4)
• EPA Substance Registry System: 1-[hydroxy(tosyloxy)iodo]-1H,1H-perfluoroethane(166903-46-4)

Safety Data

• Hazardous Substances Data: 166903-46-4(Hazardous Substances Data)

Upstream product

• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 104-15-4 toluene-4-sulfonic acid 
• 100422-04-6 (2,2,2-trifluoroethyl)-λ³-iodanediyl bis(2,2,2-trifluoroacetate) 
• 6192-52-5 p-toluenesulfonic acid monohydrate 

Downstream Products

• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 81447-34-9 2-(tosyloxy)cyclohexanone 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 
• 5433-22-7 cis-1,2-bis(tosyloxy)cyclohexane 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 

Relevant articles and documents

1-[hydroxy(sulfonyloxy)iodo]-1H,1H-perfluoroalkanes: Stable, fluoroalkyl analogs of Koser's reagent

1-[Hydroxy(sulfonyloxy)iodo]-1H,1H/-perfluoroalkanes 3 [RfCH2I(OH)OSO2R; R = CH3, CH3, p-CH3C6H4, Rf = CF3, C2F5] can be pr

Facile synthesis of Koser's reagent and derivatives from iodine or aryl iodides

The first one-pot synthesis of neutral and electron-rich [hydroxy(tosyloxy)iodo]arenes (HTIBs) from iodine and arenes is presented, thereby avoiding the need for expensive iodine(III) precursors. A large set of HTIBs, including a polyfluorinated analogue, can be obtained from the corresponding aryl iodide under the same conditions. The reaction proceeds under mild conditions, without excess reagents, and is fast and high-yielding. Together, the two presented routes give access to a wide range of HTIBs, which are useful reagents in a variety of synthetic transformations.

1-[Hydroxy(sulfonyloxy)iodo]-2,2,2-trifluoroethanes, CF3CH2I(OH)OSO2R: Stable, fluoroalkyl analogs of Koser's reagent

1-[Hydroxy(sulfonyloxy)iodo]-2,2,2-trifluoroethanes [CF3CH2I(OH)OSO2R; R = CH3, CF3, p-CH3C6H4] can be prepared in two steps from trifluoroethyliodide by oxidation with pertrifluoroacetic acid and subsequent reaction with TsOH, MsOH, or Me3SiOTf. Reaction of the tosylate derivative 3 with silyl enol ethers affords α-tosyloxyketones, while triflate 5 smoothly reacts with trimethylsilylbenzene to give the respective trifluoroethyl(phenyl)iodonium triflate 8.