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

• 108-94-1 cyclohexanone 
• 440365-99-1 3,5-bis(trifluoromethyl)-1-[hydroxy(tosyloxy)iodo]benzene 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 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 
• 166903-46-4 1-[hydroxy(tosyloxy)iodo]-1H,1H-perfluoroethane 
• 931-17-9 1,2-Cyclohexanediol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 93916-11-1 1,2-divinyl-cyclohexan-1-ol 
• 21336-06-1 1,2-diethynylcyclohex-1-ene 
• 108-94-1 cyclohexanone 

Relevant articles and documents

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.

Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones

The reactivity of enol esters toward [hydroxy(tosyloxy)iodo]benzene (HTIB) was assessed. These substrates were found to be rapidly converted in high yields to their corresponding α-tosyloxy ketones. This transformation demonstrates that these substrates can act as ketone surrogates. The scope of the method was investigated and aromatic, aliphatic, and cyclic enol esters were found to be suitable substrates for the reaction. The relative reactivity of a model substrate toward HTIB and m-CPBA was investigated, and it was found that the reaction could be performed under catalytic conditions.

One-Pot Protocol for Synthesis of -Organosulfonyloxy Ketones from Secondary Alcohols Using Hypervalent Iodine(V)-Mediated Oxidations

Tosyloxy ketones and -mesyloxy ketones were directly prepared from alcohols in one pot by treatment with hypervalent iodine(V) reagents in combination with p-toluenesulfonic acid and methanesulfonic acid, respectively, in moderate to good yields. Reaction