50487-70-2

Usage

Uses

Used in Polymer Synthesis:
N-Allylbenzenesulfonamide is used as a crosslinking agent for the synthesis of polymers, particularly in the production of thermoset resins and rubbers. Its ability to form carbon-nitrogen bonds makes it a valuable component in creating durable and stable polymer materials.
Used in Organic Synthesis:
In the realm of organic synthesis, N-Allylbenzenesulfonamide serves as a reagent, especially in the formation of carbon-nitrogen bonds. This function is crucial for the development of various organic compounds and contributes to the advancement of chemical research.
Used in Pharmaceutical and Biotechnology Research:
N-Allylbenzenesulfonamide has been studied for its potential biological activity, including antimicrobial and antiviral properties. Its application in this field highlights its potential use in the development of new drugs and treatments for various diseases.
Used in Chemical Industry:
Due to its solubility in water and most organic solvents, N-Allylbenzenesulfonamide finds use in various chemical processes and formulations within the chemical industry. Its versatility as a chemical compound makes it a valuable asset in numerous applications.

InChI:InChI=1/C9H11NO2S/c1-2-8-10-13(11,12)9-6-4-3-5-7-9/h2-7,10H,1,8H2

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 107-11-9 1-amino-2-propene 
• 98-10-2 benzenesulfonamide 
• 7575-57-7 allyl benzenesulfonate 
• 108-88-3 toluene 
• 106-95-6 allyl bromide 
• 938-10-3 phenylsulfonyl azide 
• 24850-33-7 allyltributylstanane 
• 76-63-1 allytriphenyltin 
• 100-46-9 benzylamine 
• 1017238-68-4 N-allylbenzenesulfinamide 
• 2622-05-1 allylmagnesium bromide 
• 875559-85-6 N-allyl-N-(3-methylbut-2-en-1-yl)benzenesulfonamide 
• 99606-67-4 N-(3-methylbut-2-en-1-yl)benzenesulfonamide 

Downstream Products

• 50487-74-6 N-(2,3-dibromo-propyl)-benzenesulfonamide 
• 66897-92-5 N-Allyl-N-[1-(4-methoxy-phenyl)-ethyl]-benzenesulfonamide 
• 66897-91-4 N-Allyl-N-(1-p-tolyl-ethyl)-benzenesulfonamide 
• 66897-88-9 N-Allyl-N-[1-(3-chloro-phenyl)-ethyl]-benzenesulfonamide 
• 66897-89-0 N-allyl-N-(α-methyl-4-chlorobenzyl)benzenesulfonamide 
• 66896-83-1 N-allyl-2-iodo-N-phenylsulfonylbenzamide 
• 66897-87-8 N-Allyl-N-[1-(2-chloro-phenyl)-ethyl]-benzenesulfonamide 
• 66897-34-5 N-Allyl-N-(3,6-dichloro-2-methoxy-benzoyl)-benzenesulfonamide 
• 66897-90-3 N-Allyl-N-[1-(2,4-dichloro-phenyl)-ethyl]-benzenesulfonamide 
• 66897-46-9 N-Allyl-N-(2,3,5-trichloro-6-methoxy-benzoyl)-benzenesulfonamide 
• 66896-84-2 N-Allyl-N-(3-chloro-benzoyl)-benzenesulfonamide 
• 66896-80-8 N-allyl-2-chloro-N-phenylsulfonylbenzamide 
• 66896-89-7 N-Allyl-N-(4-methoxy-benzoyl)-benzenesulfonamide 
• 66896-87-5 N-Allyl-N-(2-methyl-benzoyl)-benzenesulfonamide 

Relevant academic research and scientific papers

Twofold Radical-Based Synthesis of N, C-Difunctionalized Bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C-I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.

Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes

An efficient copper(I)-catalyzed enyne oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts.

Harnessing Energy-Transfer in N-Centered Radical-Mediated Synthesis of Pyrrolidines

Atom transfer radical addition (ATRA), cyclization (ATRC), and polymerization (ATRP) are valuable synthetic methods for the functionalization of olefins. With the advent of photoredox catalysis, visible-light became a popular tool for the initiation of these reactions. We have developed a protocol that enables easy access to distally functionalized pyrrolidines employing blue-light mediated atom transfer radical [3+2] cyclization. The reaction is scalable, proceeds at very mild conditions. tolerates various functional groups, and provides the corresponding products in good to excellent yields. If rigid olefins are utilized as the reaction partners, the products can be isolated as single diastereomers. The mechanistic investigations provide strong support for an energy-transfer mechanism.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Hypervalent Iodine Mediated Sulfonamide Synthesis

A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.

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.

CONTRAST AGENTS

The present invention relates to new class of functionalized polyazamacrocycles including at least one phosphonic or phosphinic group linked to a nitrogen atom of the macrocyclic cage, and capable of chelating paramagnetic metal ions, their chelated compl

Silver(I)-Catalyzed Deprenylation of Allylsulfonamide Derivatives

The silver(I)-catalyzed deprenylation of sulfonamide bearing prenyl functional groups on the nitrogen atom has been developed. In this reaction, the prenyl moiety was selectively eliminated without allyl or benzyl cleavage on the nitrogen atom. In addition, geranyl was also applicable for this elimination reaction. Furthermore, sulfonamide possessing two prenyl groups underwent a double deprenylation to form the corresponding deprenylated sulfonamide. Thus, a novel reactivity between the silver cation and double bond was observed.

UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides

A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.