21230-07-9

Usage

Uses

Used in Organic Synthesis:
Benzenesulfonamide, 4-methyl-N-(1-methylethyl)-, is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, such as nucleophilic substitutions, electrophilic aromatic substitutions, and rearrangement reactions. This makes it a valuable component in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzenesulfonamide, 4-methyl-N-(1-methylethyl)-, is used as a building block for the synthesis of various drug candidates. Its ability to form stable derivatives and participate in diverse chemical reactions makes it a promising candidate for the development of new drugs with improved therapeutic properties.
Used as Alkylating Reagents:
Benzenesulfonamide, 4-methyl-N-(1-methylethyl)-, is used as an alkylating reagent in the N-alkylation of sulfonamides using inactive ethers. This application is particularly relevant in the synthesis of various sulfonamide-based compounds, which have a wide range of applications in the pharmaceutical and chemical industries.

Upstream product

• 75-31-0 isopropylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-20-3 di-isopropyl ether 
• 70-55-3 toluene-4-sulfonamide 
• 104-15-4 toluene-4-sulfonic acid 
• 29281-83-2 4-methylbenzensulphonamide potassium salt 
• 67-63-0 isopropyl alcohol 
• 84461-21-2 isopropylammonium tosylate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1858-86-2 Ethyl p-toluenesulfinate 
• 6873-86-5 p-Toluolsulfinsaeure-isopropylamid 
• 2232-08-8 N-tosylimidazole 
• 51060-12-9 1-tosyl-2,3-dimethylimidazolium chloride 
• 29981-92-8 1-tosyl-3-methyl-imidazolium chloride 

Downstream Products

• 1629894-53-6 C₁₀H₁₄INO₂S 

Relevant academic research and scientific papers

Intramolecular NC rearrangements involving sulfonamide protecting groups

The reaction of amine derivatives orthogonally protected with an aryl sulfonamide and a carbamate, via a base-mediated nitrogen to carbon rearrangement is reported. This noteworthy isomerisation has implications for the use of sulfonamide protecting group

Functionalization of α-C(sp3)?H Bonds in Amides Using Radical Translocating Arylating Groups

α-C?H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3)?H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO2 extrusion.

Au(I)-Catalyzed Oxidative Functionalization of Yndiamides

Yndiamides, underexplored cousins of ynamides, offer rich synthetic potential as doubly nitrogenated two carbon building blocks. Here we report a gold-catalyzed oxidative functionalization of yndiamides to access unnatural amino acid derivatives, using a wide range of nucleophiles as a source of the amino acid side chain. The transformation proceeds under mild conditions, is highly functional group tolerant, and displays excellent regioselectivity through subtle steric differentiation of the yndiamide nitrogen atom substituents.

Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications

Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.

Structurally Diverse Synthesis of Five-, Six-, and Seven-Membered Benzosultams through Electrochemical Cyclization

We have developed a metal- and oxidant-free approach to structurally diverse synthesis of benzosultams from aryl sulfonamides through an electrochemical cyclization. Upon variation of the ortho substituent on aryl sulfonamides, five-, six-, and seven-memb

Time-Resolved EPR Revealed the Formation, Structure, and Reactivity of N -Centered Radicals in an Electrochemical C(sp3)-H Arylation Reaction

Electrochemical synthesis has been rapidly developed over the past few years, while a vast majority of the reactions proceed through a radical pathway. Understanding the properties of radical intermediates is crucial in the mechanistic study of electroche

Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

Functionalization at the α-position of carbonyl compounds has classically relied on enolate chemistry. As a result, the generation of a new C-X bond, where X is more electronegative than carbon requires an oxidation event. Herein we show that, by rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides. More than 60 examples are presented to establish the generality of this process, and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodology.

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex

The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.

A palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O

A novel palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O has been disclosed. H2O as an ideal hydrogen source was activated by B2pin2 to furnish allylamines or enamines with a broad functional group tolerance. The regioselectivity for both of the two products was up to 99:1 for most of the examples, which was achieved by adjusting the addition order of the catalyst and iodobenzene derivatives. The tentative investigation of the mechanism proved the reaction to be a non-radical process and the deuterium-labeled experiments indicated that the hydrogen was from H2O.

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.