25630-24-4

Basic information

• Product Name: N,N-DIALLYLBENZENESULFONAMIDE
• Synonyms: N,N-DIALLYLBENZENESULFONAMIDE;Nsc77919
• CAS NO: 25630-24-4
• Molecular Formula: C₁₂H₁₅NO₂S
• Molecular Weight: 237.32
• Mol File: 25630-24-4.mol

Chemical Properties

• Boiling Point: 345.3°Cat760mmHg
• Flash Point: 162.6°C
• Appearance: /
• Density: 1.123g/cm³
• Vapor Pressure: 6.22E-05mmHg at 25°C
• Refractive Index: 1.545
• PKA: -6.40±0.70(Predicted)
• CAS DataBase Reference: N,N-DIALLYLBENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIALLYLBENZENESULFONAMIDE(25630-24-4)
• EPA Substance Registry System: N,N-DIALLYLBENZENESULFONAMIDE(25630-24-4)

Safety Data

• Hazardous Substances Data: 25630-24-4(Hazardous Substances Data)

Usage

Uses

Used in Rubber and Plastics Industry:
N,N-Diallylbenzenesulfonamide is used as a crosslinking agent for improving the properties of vulcanized polymers. It enhances their resistance to heat, oil, and aging processes, which in turn increases the durability and performance of rubber and plastic products.
Used in Antimicrobial Applications:
Due to its antimicrobial properties, N,N-Diallylbenzenesulfonamide is used in various applications where controlling microbial growth is necessary. This makes it suitable for use in industries such as healthcare, food packaging, and water treatment, where preventing the growth of bacteria and other microorganisms is crucial for maintaining safety and quality.

InChI:InChI=1/C12H15NO2S/c1-3-10-13(11-4-2)16(14,15)12-8-6-5-7-9-12/h3-9H,1-2,10-11H2

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 124-02-7 diallylamine 
• 873-55-2 sodium benzenesulfonate 
• 874480-14-5 O-benzoyl-N,N-diallylhydroxylamine 
• 50487-70-2 N-allylbenzenesulfonamide 
• 7575-57-7 allyl benzenesulfonate 
• 98-10-2 benzenesulfonamide 
• 106-95-6 allyl bromide 
• 108-88-3 toluene 

Downstream Products

• 25630-21-1 4-benzenesulfonyl-2,6-bis-chloromethyl-thiomorpholine 
• 91639-34-8 2,6-bis(iodomethyl)-4-(phenylsulfonyl)morpholine 
• 80662-90-4 N,N-bis(3-hydroxypropyl)benzenesulfonamide 
• 124982-60-1 1,1-Dichloro-2,6-dichloromethyl-4-phenylsulfonylperhydro-1,4-tellurazine 
• 124982-62-3 2,6-Dibromomethyl-4-phenylsulfonylperhydro-1,4-selenazine 
• 124982-56-5 1,1-Dibromo-2,6-dibromomethyl-4-phenylsulfonylperhydro-1,4-selenazine 
• 125022-55-1 2,6-Dichloromethyl-4-phenylsulfonylperhydro-1,4-selenazine 
• 124982-57-6 1,1-Dichloro-2,6-dichloromethyl-4-phenylsulfonylperhydro-1,4-selenazine 
• 80662-89-1 N-benzenesulfonyl-2-methyl-4-azacycloheptanone 
• 80662-88-0 N-benzenesulfonyl-5-azacyclooctanone 
• 16851-82-4 N-phenylsulfonylpyrrole 
• 16851-71-1 1-(benzenesulfonyl)-2,5-dihydro-1H-pyrrole 
• 97462-72-1 N-(phenylsulfonyl)-3-methyl-4-methylenepyrrolidine 
• 97462-73-2 N-(phenylsulfonyl)-2-methylenepiperidine 

Relevant articles and documents

Synthesis of N -Sulfonyl- and N -Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

N -Sulfonyl- and N -acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf) 2/s

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.

Synthesis and structures of 9-oxabispidine analogues of cisplatin, carboplatin, and oxaliplatin

The literature synthesis of 9-oxabispidine [OC6H10(NH)2, C] has been revisited and optimized, which includes determination of the crystal structures of C, the secondary component trans-(PhSO2)NC4Hsub

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature

A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is

Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature

By using O-benzoyl hydroxylamines as amine sources, the first convenient copper-catalyzed electrophilic amination of sodium sulfinates has been realized. Even with 2 mol% catalyst loading, the protocol provided an efficient and straightforward synthesis of a broad range of functional sulfonamides under ambient reaction conditions without an additional base and ligand. Based on the control experiments, a plausible mechanism was proposed.

Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines giving 3-arylpyrrolidines: Protonation as a key step

A hydroxorhodium complex coordinated with (R)-segphos was found to catalyze the hydroarylation of 3-pyrrolines with arylboroxines under neutral conditions to give 3-arylpyrrolidines with high enantioselectivity in high yields.

Benzenesulfonyl chloride with primary and secondary amines in aqueous media - Unexpected high conversions to sulfonamides at high pH

We have determined pH-yield profiles under pseudo-first-order conditions of the reactions of benzenesulfonyl chloride with a set of primary and secondary water-soluble alkylamines, and have found with certain amines, such as dibutylamine, a profile taking the form of a sigmoid pH-yield curve with relatively high yields of the sulfonamide persisting with increasing basicity up to and including 1.0 mol/L sodium hydroxide. This behaviour is quantitatively accounted for by invoking, in addition to the usual second-order reaction of the sulfonyl chloride with the amine, two third-order terms (i) one first-order in sulfonyl chloride, amine and hydroxide anion, and (H) another first-order in sulfonyl chloride and second-order in the amine. The importance of the third-order terms correlates approximately with the total number of alkyl carbon atoms in the amine, and this in turn is regarded as related to the hydrophobic character of the amine. Experiments to test this picture included: (i) observation of a bell-shaped curve with bis(2-methoxyethyl)amine, (H) in the reaction of dibutylamine in THF-H2O (1:1), and also (iii) in the reaction of dibutylamine in 1.0 mol/L tetrabutylammonium bromide, and (iv) increase in the contributions of the third-order terms in 1.0 mol/L aqueous sodium chloride. Preparative reactions with dibutylamine, 1-octylamine, and hexamethylenimine in 1.0 mol/L aqueous sodium hydroxide with a 5% excess of benzenesulfonyl chloride gave, respectively, 94%, 98%, and 97% yields of the corresponding sulfonamides.

Optimizing the 5-exo/6-endo ratio of vinyl radical cyclizations through catalysis with diphenyl diselenide

The 5-exo/6-endo product ratio in the stannane mediated cyclizations of vinyl iodides is very significantly improved by operating in the presence of catalytic PhSeSePh with no loss in overall cyclization yield.

Synthesis of the Pyrrolidine Ring System by Radical Cyclization

A series of bromo-substituted allyl- and diallyl-substituted sulfonamides have been found to undergo free radical cyclization when treated with tri-n-butyltin hydride in the presence of AIBN.The regiochemical course of the cyclization depends on the nature of the substituent groups attached to the ?-bond.The stereoelectronic factors governing the cyclization reaction of these N-allylsulfonamides are even more stringent than those which occur with the simple 5-hexenyl system.This is probably related to the shorter C-N bond distance which promotes the 5-exo trigcyclization pathway.The present method provides an attractive entry to the preparation of pyrrolidines from easily available N-(2-bromoethyl)-N-allyl- and N-(2-bromopropenyl)-N-allylsulfonamides.The method represents a clear-cut example of the use of hetero-substituted radicals in C-C bond-forming processes.