66558-04-1

Basic information

• Product Name: Benzenesulfonamide, 4-methyl-N-[(1S)-1-phenylethyl]-
• CAS NO: 66558-04-1
• Molecular Formula: C15H17NO2S
• Molecular Weight: 275.371
• Mol File: 66558-04-1.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 4-methyl-N-[(1S)-1-phenylethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-methyl-N-[(1S)-1-phenylethyl]-(66558-04-1)
• EPA Substance Registry System: Benzenesulfonamide, 4-methyl-N-[(1S)-1-phenylethyl]-(66558-04-1)

Safety Data

• Hazardous Substances Data: 66558-04-1(Hazardous Substances Data)

Upstream product

• 24865-83-6 (E)-1-phenyl-N-tosylethanimine 
• 929632-72-4 C₁₇H₁₆F₃NO₃S 
• 407-25-0 trifluoroacetic anhydride 
• 100-41-4 ethylbenzene 
• 127-65-1 chloroamine-T 
• 24865-83-6 4-methyl-N-(1-phenylethylidene)benzenesulfonamide 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 544-97-8 dimethyl zinc(II) 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 70-55-3 toluene-4-sulfonamide 
• 17264-54-9 sodium p-methylbenzoate 
• 98-86-2 acetophenone 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 

Downstream Products

• 155694-28-3 4-Methyl-N-((R)-5-methyl-cyclopent-1-enylmethyl)-N-((S)-1-phenyl-ethyl)-benzenesulfonamide 
• 155694-27-2 4-Methyl-N-((S)-5-methyl-cyclopent-1-enylmethyl)-N-((S)-1-phenyl-ethyl)-benzenesulfonamide 
• 929632-72-4 C₁₇H₁₆F₃NO₃S 
• 156303-48-9 (+)-(S)-4-methyl-N-(1-phenylethyl)-N-tosylbenzenesulfonamide 
• 1176193-81-9 C₁₈H₁₉NO₂S 
• 155694-30-7 (R)-2-((1R,3S)-3-Methyl-2-methylene-cyclopentyl)-N-((S)-1-phenyl-ethyl)-propionamide 
• 155694-29-4 N-((S)-5-Methyl-cyclopent-1-enylmethyl)-N-((S)-1-phenyl-ethyl)-propionamide 
• 155694-31-8 (R)-2-((1S,2R,3S)-2-Hydroxymethyl-3-methyl-cyclopentyl)-N-((S)-1-phenyl-ethyl)-propionamide 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Relevant articles and documents

Optically active lithium-alkoxide catalyzed asymmetric reduction of imines with trimethoxyhydrosilane

Optically active lithium alkoxide catalyzed asymmetric reduction of imines with trimethoxhydroysilane in moderate enantioselectivity (up to 72% ee).

Electrochemical synthesis of sulfonamides in a graphite powder macroelectrode

The electrochemical generation of sulfinyl radicals from commercially available and non-expensive sodium salts of sulfinic acids is described. Electrooxidation reactions were carried out in a graphite powder macroelectrode using an aqueous electrolyte and cavity cell. Further reaction with primary or secondary amines gave the corresponding sulfonamides, a unit present in several biologically active compounds and pharmaceuticals, in good yields.

Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex

Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.

PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes

A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.