137595-22-3

Basic information

• Product Name: Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-2-phenyl-
• CAS NO: 137595-22-3
• Molecular Formula: C16H17NO2S
• Molecular Weight: 287.382
• Mol File: 137595-22-3.mol
• Article Data: 41

Chemical Properties

• CAS DataBase Reference: Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-2-phenyl-(137595-22-3)
• EPA Substance Registry System: Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-2-phenyl-(137595-22-3)

Safety Data

• Hazardous Substances Data: 137595-22-3(Hazardous Substances Data)

Upstream product

• 127-65-1 chloroamine-T 
• 98-83-9 isopropenylbenzene 
• 41085-71-6 bromamine T 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 98-86-2 acetophenone 
• 1058-14-6 N-p-tolylsulfonylphosphine imide 
• 70-55-3 toluene-4-sulfonamide 
• 21849-40-1 dibromamine-T 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 

Downstream Products

• 1160286-77-0 3-methyl-3,5-diphenyl-1-tosyl-2,3-dihydro-1H-pyrrole 
• 1188273-65-5 5-(4-methoxyphenyl)-3-methyl-3-phenyl-1-tosyl-2,3-dihydro-1H-pyrrole 
• 1188273-76-8 N-(4-(4-methoxyphenyl)-2-methyl-4-oxo-2-phenylbutyl)-4-methylbenzenesulfonamide 
• 58107-54-3 N-(2-hydroxy-2-phenylpropyl)-4-methylbenzene-sulfonamide 

Relevant articles and documents

Iridium-Catalyzed Isomerization of N-Sulfonyl Aziridines to Allyl Amines

The Crabtree's reagent catalyzes the isomerization of N-sulfonyl 2,2-disubstituted aziridines to allyl amines. The selectivity of allyl amine vs imine is very high (up to 99/1). The unprecedented isomerization takes place in mild conditions without activation of the catalyst by hydrogen. The mechanism has been studied computationally by DFT calculations; instead of the usual hydrogenation of COD, the catalytic species is formed by a loss of the pyridine ligand. Approaching of aziridine to this unsaturated species leads to a carbocation intermediate through a low energy barrier. A metal-mediated tautomerization involving sequentially γ-H elimination and N-H reductive elimination affords selectively the allyl amine. The readiness of the CγH bond to participate in the H elimination step accounts for the selectivity toward the allyl amine product.

Catalytic asymmetric heterogeneous aziridination of alkenes using zeolite CuHY with [N-(p-tolylsulfonyl)imino]phenyliodinane as nitrene donor

Copper-exchanged zeolite Y (CuHY) is found to be a highly effective heterogeneous catalyst for the aziridination of alkenes using [N-(p-tolylsulfonyl)imino]phenyliodinane (PhI=NTs) as the nitrogen source. Exchange of zeolite Y with other cations (Ag+

Iron(III) porphyrin catalyzed aziridination of alkenes with bromamine-T as nitrene source

Equation presented. Iron(III) porphyrin complexes Fe(Por)Cl are effective catalysts for aziridination of alkenes using bromamine-T as the nitrene source. The catalytic system can operate under mild conditions with alkenes as limiting reagents. The aziridi

Practical aziridinations II: Electronic modifications to poly(pyrazolyl)borate-copper catalysts

A significant influence of the electronic features of poly(pyrazolyl)borate ligands on the efficiency of the copper-catalyzed aziridination reaction has been noted. Electron-deficient, bidentate di(pyrazolyl)borates in conjunction with copper(II) chloride

Is the Electrophilicity of the Metal Nitrene the Sole Predictor of Metal-Mediated Nitrene Transfer to Olefins? Secondary Contributing Factors as Revealed by a Library of High-Spin Co(II) Reagents

Recent research has highlighted the key role played by the electron affinity of the active metal-nitrene/imido oxidant as the driving force in nitrene additions to olefins to afford valuable aziridines. The present work showcases a library of Co(II) reage

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

Synthesis of indolines: Via a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides

A Pd- and norbornene-catalyzed domino procedure has been developed to synthesize indoline compounds. This reaction provides efficient access to indolines by employing aryl iodides with aziridines as new electrophiles. The transformation is scalable and tolerates a range of functional groups.