1821-40-5

Usage

Uses

Used in Plastics and Rubber Industry:
N-ethyl-4-methyl-N-phenyl-benzenesulfonamide is used as a UV stabilizer for preventing degradation and discoloration of plastics and rubber materials caused by harmful UV radiation.
Used in Polymer Production:
N-ethyl-4-methyl-N-phenyl-benzenesulfonamide is used as an additive to improve the heat resistance and durability of polymer materials.
Used in Pharmaceutical and Agrochemical Synthesis:
N-ethyl-4-methyl-N-phenyl-benzenesulfonamide is used as a building block in the creation of various organic compounds for pharmaceuticals and agrochemicals.

InChI:InChI=1/C15H17NO2S/c1-3-16(14-7-5-4-6-8-14)19(17,18)15-11-9-13(2)10-12-15/h4-12H,3H2,1-2H3

Upstream product

• 64-67-5 diethyl sulfate 
• 68-34-8 phenyl toluenesulfonamide 
• 557-20-0 diethylzinc 
• 98-95-3 nitrobenzene 
• 98-59-9 p-toluenesulfonyl chloride 
• 613-97-8 N-methyl-N-ethylaniline 
• 16078-91-4 N-allyl-N-ethylaniline 
• 91-66-7 N,N-diethylaniline 
• 103-69-5 N-ethyl-N-phenylamine 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 64-17-5 ethanol 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 

Downstream Products

• 1213-33-8 o-aminophenyl p-tolyl sulfone 
• 101113-21-7 toluene-4-sulfonic acid-(N-ethyl-4-nitro-anilide) 
• 53973-79-8 N-ethyl-2-(toluene-4-sulfonyl)-aniline 

Relevant academic research and scientific papers

KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines: Synthesis of amides and sulfonamides

KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines producing secondary amine was introduced, which was trapped by electrophiles (acyl chloride and sulfonyl chloride) to form amides and sulfonamides. The reaction could take place at mild condition, tolerating a wide range of function groups and affording products in moderate to excellent yields.

Mild alkaline hydrolysis of hindered esters in non-aqueous solution

Sterically hindered esters of carboxylic acids, which are considered very resistant to saponification, were rapidly and efficiently saponified in a non-aqueous medium using NaOH in MeOH/CH2Cl2 (1:9) at room temperature. Furthermore, this reaction protocol was extended and successfully applied to the hydrolysis of tosylates and N-tosyl indoles.

Electrophilic Amination with Nitroarenes

An exceptionally general electrophilic amination, which directly transforms commercially available nitroarenes into alkylated aromatic aminoboranes with zinc organyl compounds was developed. The reaction starts with a two-step partial reduction of the nitro group to a nitrenoid, which is used in situ as the electrophilic amination reagent. To facilitate isolation, the resulting air- and moisture-sensitive aminoboranes were reacted with a range of electrophiles. The method not only represents a direct transformation of nitro compounds into electrophilic amination reagents but also provides an elegant alternative to dehydrocoupling methods for the generation of aminoboranes.

Palladium-Catalyzed cascade sp2 c?H bond functionalizations allowing one-Pot access to 4?Aryl-1,2,3,4-tetrahydroquinolines from n?Allyl?N?arylsulfonamides

We have developed a palladium-catalyzed cascade reaction allowing an efficient synthesis of 4-aryl-1,2,3,4-tetrahydroquinolines from N-allyl-N-arylsulfonamides and benzenesulfonyl chlorides. In this transformation, two C(sp2)?C(sp3) bonds were formed via activation of C(sp2)?H bonds. The reaction proceeds using the easily accessible catalyst PdCl2, with Li2CO3 as inexpensive base and CuBr as additive, and tolerates a wide variety of substituents on both reaction partners.

Synthesis of sulfonamides: Via copper-catalyzed oxidative C-N bond cleavage of tertiary amines

A copper-catalyzed coupling reaction of sulfonyl chlorides with tertiary amines via the oxidative C-N bond cleavage of tertiary amines was developed. Sulfonamides were synthesized using this strategy in moderate to good yields. The reaction was applicable to various tertiary amines, as well as sulfonyl chlorides.

NH4I-Catalyzed Synthesis of Sulfonamides from Arylsufonylhydrazides and Amines

A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to good yields. Possible reaction pathway for the formation of the products was also discussed in this paper. Sulfonimides were synthesized through the oxidation coupling of arylsufonylhydrazides and amines by TBHP/NH4I system in moderate to good yields.

Solvent effects in the arenesulfonylation of N-alkylanilines

The kinetics of arenesulfonylation of N-methyl- and N-ethylaniline with 3-nitro- and 4-methylbenzenesulfonyl chlorides in aqueous 1,4-dioxane have been studied. Comparison of the solvent effects on the reaction of N-alkylanilines with arenesulfonyl chlori

Visible light-mediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts

Herein, the development of visible light-mediated atom transfer radical addition (ATRA) of haloalkanes onto alkenes and alkynes using the reductive and oxidative quenching of [Ir{dF(CF3)ppy}2(dtbbpy)]PF 6 and [Ru(bpy)3]Cl2 is presented. Initial investigations indicated that the oxidative quenching of photocatalysts could effectively be utilized for ATRA, and since that report, the protocol has been expanded by broadening the scope of the reaction in terms of the photocatalysts, substrates, and solvents. In addition, further modifications of the reaction conditions allowed for the efficient ATRA of perfluoroalkyl iodides onto alkenes and alkynes utilizing the reductive quenching cycle of [Ru(bpy) 3]Cl2 with sodium ascorbate as the sacrificial electron donor. These results signify the complementary nature of the oxidative and reductive quenching pathways of photocatalysts and the ability to predictably direct reaction outcome through modification of the reaction conditions.

A practical, water-soluble, ionic scavenger for the solution-phase syntheses of amides

A new ionic, water-soluble scavenger for acyl chlorides, 1-(2-aminoethyl)pyridinium bromide (1), has been investigated. Compound 1 was used for the rapid and simple purification of a series of benzamides and sulfonamides (Table) obtained by solution-phase synthesis from the corresponding amines (Scheme). The inexpensive scavenger, which can be prepared on large scale, was shown to readily 'eliminate' excess acyl chlorides (reagent) by simple aqueous extraction. The amides purified in this way were obtained in excellent yields and purities (Table), which makes 1 a versatile new reagent, especially for the combinatorial solution-phase synthesis of amide libraries.

Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds

The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.