21969-24-4

Basic information

• Product Name: N,4-Dimethyl-N-(4-methoxyphenyl)benzenesulfonamide
• Synonyms: N-(4-Methoxyphenyl)-N,4-dimethylbenzenesulfonamide;N,4-Dimethyl-N-(4-methoxyphenyl)benzenesulfonamide
• CAS NO: 21969-24-4
• Molecular Formula: C₁₅H₁₇NO₃S
• Molecular Weight: 291.37
• Mol File: 21969-24-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,4-Dimethyl-N-(4-methoxyphenyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,4-Dimethyl-N-(4-methoxyphenyl)benzenesulfonamide(21969-24-4)
• EPA Substance Registry System: N,4-Dimethyl-N-(4-methoxyphenyl)benzenesulfonamide(21969-24-4)

Safety Data

• Hazardous Substances Data: 21969-24-4(Hazardous Substances Data)

Upstream product

• 1150-26-1 N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide 
• 80-48-8 methyl p-toluene sulfonate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 104-94-9 4-methoxy-aniline 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 98-59-9 p-toluenesulfonyl chloride 
• 696-62-8 para-iodoanisole 
• 512-56-1 trimethyl phosphite 
• 1146-43-6 N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide 
• 74-88-4 methyl iodide 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 197803-54-6 2-methyl-5-nitropyrimidine-4,6-bis(p-toluenesulfonate) 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 408351-58-6 4-methoxy-N-methyl-2-(toluene-4-sulfonyl)-aniline 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 14665-72-6 5-(p-Toluolsulfon-N-methylamido)-2-methoxy-benzaldehyd 

Relevant articles and documents

Cu(i) catalysed annulation of isothiocyanates/isocyanates with 2-iodo-sulfonamides: Synthesis of benzodithiazines, benzothiadiazinones, benzothiazinylidene-anilines and benzothiazolylidene-anilines

An efficient Cu(i)-catalysed cyclisation reaction of 2-iodobenzene sulfonamides with aryl-isothiocyanates and isocyanates that affords functionalised benzodithiazines and benzothiadiazinones, respectively, has been developed. Thus, in the reaction with ar

Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor

Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.

Photo-Fries rearrangement of N-arylsulfonamides to aminoaryl sulfone derivatives

Photochemical reaction of variously substituted p-toluenesulfonanilides was studied. The reaction gives rearranged products, o- and p-amino-substituted diaryl sulfones with the combined yields of 38-72%: the p-isomer is more favored over the o-isomer with the selectivity ratio of 1.1-4.3 depending on the substituents. N-Alkylation of the sulfonanilides increases the yields of the rearranged products, and e-withdrawing substituents on the N-phenyl ring does not lower the yields drastically. This study provides simple methodology for the synthesis of o- and p-aminoaryl sulfones which are otherwise not easily accessible.