2840-20-2

Basic information

• Product Name: monomethylammonium p-toluenesulfonate
• CAS NO: 2840-20-2
• Molecular Weight: 203.262
• Mol File: 2840-20-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: monomethylammonium p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: monomethylammonium p-toluenesulfonate(2840-20-2)
• EPA Substance Registry System: monomethylammonium p-toluenesulfonate(2840-20-2)

Safety Data

• Hazardous Substances Data: 2840-20-2(Hazardous Substances Data)

Upstream product

• 60-35-5 acetamide 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 108-88-3 toluene 

Downstream Products

• 15569-85-4 cotinine 
• 863094-23-9 3-methylamino-1-thiophen-2-yl-propan-1-one p-toluenesulfonate 

Relevant articles and documents

Synthesis of alkylammonium tosylates with poly{[4-hydroxy(tosyloxy)iodo] styrene}

Several primary carboxamides (RCONH2) were converted to the corresponding alkylammonium tosylates (RN+H3 -OTs) with poly{[4-hydroxy (tosyloxy) iodo]styrene} (PSHTIB) in yields ranging from 60% to 90%.

Direct Conversion of Aliphatic Carboxamides to Alkylammonium Tosylates with benzene

The utility of benzene (2) as a "Hofmann reagent" has been explored.Treatment of various primary, aliphatic carboxamides (RCONH2, R = methyl, ethyl, isopropyl, tert-butyl, n-pentyl, n-heptyl, undecyl, allyl, benzyl, cyclobutyl, cyclohexyl) with 2 in acetonitrile at reflux gave the corresponding alkylammonium tosylates (RN+H3-OTs) in yields ranging from 57percent to 94percent.The alkylammonium tosylates separated directly from the solvent when the reaction mixtures were kept at room temperature or below.When α-phenylacetamide was allowed to react with 2 in ethanol, ethyl benzylcarbamate (4) was obtained in 50percent yield, a result consistent with the intermediate existence of benzyl isocyanate in this reaction.A mechanism for the conversion of carboxamides by 2 to alkylammonium tosylates, involving the initial formation of N-phenyl iodonio amides and their collapse to iodobenzene and alkyl isocyanates, is proposed.The reaction of malonamide with 2 in acetonitrile followed a divergent course: 2-(tosyloxy)malonamide (3) was obtained in ca. 81percent yield (crude).