50487-71-3

Basic information

• Product Name: N-allyl-4-methylbenzenesulfonamide
• Synonyms: N-Allyl-p-toluenesulfonaMide;N-Allyl-p-toluenesulfonamide;N-allyl-4-methylbenzenesulfonamide
• CAS NO: 50487-71-3
• Molecular Formula: C₁₀H₁₃NO₂S
• Molecular Weight: 211.28072
• Mol File: 50487-71-3.mol
• Article Data: 155

Chemical Properties

• Melting Point: 61.0 to 65.0 °C
• Boiling Point: 326.6°Cat760mmHg
• Flash Point: 151.3°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 0.000213mmHg at 25°C
• Refractive Index: 1.536
• Solubility: soluble in Methanol
• PKA: 10.92±0.50(Predicted)
• CAS DataBase Reference: N-allyl-4-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-allyl-4-methylbenzenesulfonamide(50487-71-3)
• EPA Substance Registry System: N-allyl-4-methylbenzenesulfonamide(50487-71-3)

Safety Data

• Hazardous Substances Data: 50487-71-3(Hazardous Substances Data)

Usage

Uses

N-Allyl-p-toluenesulfonamide is a useful catalyst in the process of ring-closing enyne metathesis using Grubbs I type catalysts.

Synthesis Reference(s)

Tetrahedron Letters, 20, p. 623, 1979 DOI: 10.1016/S0040-4039(01)86019-6

InChI:InChI=1/C10H13NO2S/c1-3-8-11-14(12,13)10-6-4-9(2)5-7-10/h3-7,11H,1,8H2,2H3

Upstream product

• 591-87-7 Allyl acetate 
• 18522-92-4 sodium p-toluenesulfonamide 
• 169137-89-7 S-(prop-2-enyl)-S-phenyl-N-(p-tolylsulfonyl) sulfoximide 
• 941-55-9 4-toluenesulfonyl azide 
• 24850-33-7 allyltributylstanane 
• 76-63-1 allytriphenyltin 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 762-72-1 allyl-trimethyl-silane 
• 154139-24-9 N-allyl-N-(2-bromo-acetyl)-4-methyl-benzenesulfonamide 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 117794-75-9 N-allyl-N-[2-(phenyl)prop-2-en-1-yl]-N-(p-toluenesulfonyl)amide 
• 594-19-4 tert.-butyl lithium 
• 107-11-9 1-amino-2-propene 
• 7466-04-8 2,4,6-trichlorophenyltosylate 

Downstream Products

• 56643-09-5 N,N'-Diallyl-N,N'-tetramethylen-bis-(p-toluolsulfonamid) 
• 129748-59-0 N-tosyl-N-(5-bromopentyl)allylamine 
• 155088-02-1 N-allyl-N-tosyl-α,α-dichloroacetamide 
• 116043-28-8 N-Allyl-4-methyl-N-((E)-octa-2,7-dienyl)-benzenesulfonamide 
• 106003-71-8 N-allyl-N'-(2,7-octadienyl)-p-toluenesulfamide 
• 154139-24-9 N-allyl-N-(2-bromo-acetyl)-4-methyl-benzenesulfonamide 
• 129748-57-8 N-allyl-N-(3-bromopropyl)-4-methylbenzenesulfonamide 
• 167029-87-0 N-allyl-N-(2-bromo-propionyl)-4-methyl-benzenesulfonamide 
• 1000979-69-0 4-methyl-N-[(2E)-3-(4-methoxyphenyl)-2-propenyl]benzenesulfonamide 
• 210692-85-6 2-Methylene-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane 
• 226572-09-4 N-Allyl-N-(4-tolylsulfonyl)-2-bromo-3-methylbutanamide 
• 254759-16-5 N-Prop-2-enyl-N-(4-tolylsulfonyl)-2-chloro-2-phenylacetamide 
• 176249-70-0 N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)-4-toluenesulfonamide 
• 301832-45-1 (E)-4-methyl-N-[3-methyl-4-(phenylsulfanyl)-2-butenyl] N-(2-propenyl)benzenesulfonamide 

Relevant articles and documents

Ligand geometry effects in copper mediated atom transfer radical cyclisations

The relative rate of copper (I) mediated atom transfer radical cyclisation of (11) with a range of ligands at room temperature has been screened. The most active ligands were found to be multidentate amine ligands (6-7).

Transformation of allylic silanes into allylic amines using [N-(P- toluenesulfonyl)imino]phenyliodinane

Reaction of allylic silanes with PhI=NTs in the presence of catalytic Cu(OTf)2 provides a direct route for the preparation of allylic amines in moderate yields.

A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates

An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic studies suggest that the boron source plays a unique role in the borylation step, and in the formation of haloamine intermediates.

A Free Radical Cyclization Catalyzed by Ruthenium Hydride Species

A photolytically generated ruthenium hydride species catalyzing a free radical cyclization reaction was developed. As the new methodology ensures reproducibility of the free radical reaction of trialkyltin hydrides and a fast hydrogen transfer to the radical intermediates, the methodology provides fast quenching of radical intermediates and thus suppresses rearrangement of radical intermediates before the hydride quench. By offering new reactivity and selectivity to the trialkyltin hydride mediated free radical cyclization reactions, the methodology will find wide range of applications in organic synthesis.