81447-34-9

Basic information

• Product Name: Cyclohexanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-
• Synonyms: Cyclohexanone,2-[[(4-methylphenyl)sulfonyl]oxy];2-tosyloxycyclohexanone;(p-toluenesulfonyloxy)cyclohexanone;toluene-4-sulfonic acid 2-oxocyclohexyl ester
• CAS NO: 81447-34-9
• Molecular Formula: C13H16O4S
• Molecular Weight: 268.334
• Mol File: 81447-34-9.mol
• Article Data: 26

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-(81447-34-9)
• EPA Substance Registry System: Cyclohexanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-(81447-34-9)

Safety Data

• Hazardous Substances Data: 81447-34-9(Hazardous Substances Data)

Upstream product

• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 108-94-1 cyclohexanone 
• 104-15-4 toluene-4-sulfonic acid 
• 1424-22-2 1-cyclohexenyl acetate 
• 159950-96-6 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 
• 25370-96-1 O-(p-toluenesulfonyl)-N-tert-butoxycarbonyl-N-methylhydroxylamine 
• 25370-97-2 O-(p-toluenesulfonyl)-N-methylhydroxylamine 
• 108-93-0 cyclohexanol 
• 440365-99-1 3,5-bis(trifluoromethyl)-1-[hydroxy(tosyloxy)iodo]benzene 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 166903-46-4 1-[hydroxy(tosyloxy)iodo]-1H,1H-perfluoroethane 
• 931-17-9 1,2-Cyclohexanediol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 108-94-1 cyclohexanone 
• 71911-61-0 6-bicyclo<3.1.0>hexan-6-ol 

Relevant articles and documents

Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier

The development of practical methods to access chiral nonracemic α-substituted ketones is of particular importance due to their ubiquitous nature. Unprecedented levels of enantioselectivity are reported for the synthesis of α-tosyloxy ketones, using enol esters and chiral iodine(III) reagents. The reaction can be performed under both stoichiometric and catalytic conditions. These results suggest widely different reaction mechanisms for the reaction of ketones versus enol esters, supporting recent computational insights.

General Method for the Preparation of Electron-Deficient Imidazo[1,2-a]pyridines and Related Heterocycles

A new annulation method for the preparation of the imidazo[1,2-a]pyridine ring system under mild conditions is presented. Treatment of a 2-aminopyridine with a dimethylketal tosylate in acetonitrile at elevated temperature (80-140°C) in the presence of catalytic Sc(OTf)3 provides the imidazo[1,2-a]pyridine product in good yield. The annulation method is broadly applicable to electron-poor 2-aminopyridines and displays a complementary profile to the classic preparation of the imidazo[1,2-a]pyridine ring system by reaction of a bromoketone with electron-rich and -neutral substrates. The scope of the process and mechanistic considerations are discussed.

M-iodosylbenzoic acid: Recyclable hypervalent iodine reagent for-tosyloxylation and-mesyloxylation of ketones

m-Iodosylbenzoic acid-mediated reactions of various carbonyl compounds provided-organosulfonyloxy carbonyl compounds in good yields. The final products could be easily isolated without any chromatographic purification by simple treatment of the crude mixt