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

Description

N-Allyl-4-methylbenzenesulfonamide is an organic compound that features a sulfonylamide functional group with a specific allyl and methyl substituent pattern. It is known for its potential applications in various chemical and industrial processes due to its unique structural properties.

Uses

Used in Chemical Synthesis:
N-Allyl-4-methylbenzenesulfonamide is used as a catalyst in the process of ring-closing enyne metathesis when utilizing Grubbs I type catalysts. Its application is crucial for facilitating the formation of cyclic structures from enyne substrates, which are important in the synthesis of complex organic molecules and have potential applications in pharmaceuticals, materials science, and other related fields.

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

• 98-59-9 p-toluenesulfonyl chloride 
• 107-11-9 1-amino-2-propene 
• 591-87-7 Allyl acetate 
• 18522-92-4 sodium p-toluenesulfonamide 
• 1469-70-1 allyl ethyl carbonate 
• 70-55-3 toluene-4-sulfonamide 
• 107183-92-6 N-(propen-3' yl) N-tosyl dimethyl-1,1 ethanesulfenamide 
• 106-95-6 allyl bromide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 120568-65-2 Acetic acid (E)-4-[allyl-(toluene-4-sulfonyl)-amino]-but-2-enyl ester 
• 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 

Downstream Products

• 102654-50-2 N-(2,3-dibromopropyl)-4-methylbenzenesulfonamide 
• 56643-09-5 N,N'-Diallyl-N,N'-tetramethylen-bis-(p-toluolsulfonamid) 
• 66897-38-9 N-Allyl-N-(2,4-dichloro-benzoyl)-4-methyl-benzenesulfonamide 
• 129748-58-9 N-tosyl-N-(4-bromobutyl)allylamine 
• 2645-02-5 methyl tosylglycinate 
• 129748-59-0 N-tosyl-N-(5-bromopentyl)allylamine 
• 155088-02-1 N-allyl-N-tosyl-α,α-dichloroacetamide 
• 154139-26-1 N-allyl-N-tosyl-α,α-dimethyl-α-bromoacetamide 
• 154330-95-7 N-tosyl-α,α-dichloro-α-methyl-allylacetamide 
• 116043-28-8 N-Allyl-4-methyl-N-((E)-octa-2,7-dienyl)-benzenesulfonamide 
• 121224-75-7 Acetic acid (1R,4S)-4-[allyl-(toluene-4-sulfonyl)-amino]-cyclohex-2-enyl ester 
• 133886-44-9 2-(Toluene-4-sulfonyl)-hexahydro-cyclopenta[c]pyrrol-5-one 
• 133886-43-8 2,3,3a,4-tetrahydro-2-[(4-methylphenyl)sulfonyl]-cyclopenta[c]pyrrol-5(1H)-one 
• 134886-28-5 2,3,3a,4-tetrahydro-6-methyl-2-[(4-methylphenyl)sulfonyl]-cyclopenta[c]pyrrol-5(1H)-one 

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.

Practical Synthesis of Halogenated N-Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.