1005500-77-5

Basic information

• Product Name: N,4-dimethyl-N-(phenylethynyl)benzenesulfonamide
• Synonyms: N,4-dimethyl-N-(phenylethynyl)benzenesulfonamide
• CAS NO: 1005500-77-5
• Molecular Weight: 285.367
• Mol File: 1005500-77-5.mol
• Article Data: 49

Chemical Properties

• CAS DataBase Reference: N,4-dimethyl-N-(phenylethynyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,4-dimethyl-N-(phenylethynyl)benzenesulfonamide(1005500-77-5)
• EPA Substance Registry System: N,4-dimethyl-N-(phenylethynyl)benzenesulfonamide(1005500-77-5)

Safety Data

• Hazardous Substances Data: 1005500-77-5(Hazardous Substances Data)

Upstream product

• 1483-82-5 phenylethynyl chloride 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 58723-96-9 (Z)-1,2-dichloro-2-phenylethylene 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 536-74-3 phenylacetylene 
• 98-59-9 p-toluenesulfonyl chloride 
• 637-44-5 phenylpropyolic acid 
• 932-87-6 1-Bromo-2-phenylacetylene 

Downstream Products

• 1026133-70-9 N-[(E)-2-dimethylphenylsilyl-2-phenylethenyl]-N-methyl-p-toluenesulfonamide 
• 1026133-68-5 N-methyl-N-[(E)-2-phenyl-2-(trimethylsilyl)ethenyl]-p-toluenesulfonamide 
• 1005500-93-5 C₂₃H₂₁NO₃S₂ 
• 1268824-74-3 N-methyl-2-oxo-2-phenyl-N-p-toluenesulfonylacetamide 
• 1422721-64-9 (E)-N-(1-iodo-2-phenylvinyl)-N,4-dimethylbenzenesulfonamide 
• 1422721-65-0 (E)-N-(1-bromo-2-phenylvinyl)-N,4-dimethylbenzenesulfonamide 
• 1005500-94-6 N-methyl-N-(p-tolylsulfonyl)phenylacetamide 
• 21601-78-5 phenylmalonic acid monophenyl ester 
• 78907-06-9 N-benzyl-2-phenylglycine methyl ester 
• 1645293-10-2 C₂₂H₁₅N₅O₂S 
• 1629962-34-0 (E)-N-(1-bromo-2-iodo-2-phenylvinyl)-N,4-dimethylbenzenesulfonamide 
• 1577201-70-7 dimethyl 2-((N,4-dimethylphenyl)sulfonamido)-3-phenyl-4-(p-methylphenyl)cyclopent-2-ene-1,1-dicarboxylate 
• 1577201-88-7 dimethyl 2-((N,4-dimethylphenyl)sulfonamido)-3-phenyl-4-(thiophen-2-yl)cyclopent-2-ene-1,1-dicarboxylate 

Relevant articles and documents

α-Imino Gold Carbenes from 1,2,4-Oxadiazoles: Atom-Economical Access to Fully Substituted 4-Aminoimidazoles

A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access α-imino gold carbenes, which corresponds to an unprecedented intermolecular transfer of N-acylimino nitrenes to ynamides. Moreover, the reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale.

AgOTf-catalyzed reaction of sulfonyl hydrazones with ynamides led to stereoselective synthesis of α-amino alkenyl-substituted hydrazone derivatives

A novel method for the synthesis of α-amino alkenyl-substituted hydrazone derivatives was disclosed through silver-catalyzed reaction of sulfonyl hydrazones with ynamides. The present method features mild conditions, high stereoselectivity and good yields. The proposed mechanism involves silver-mediated generation of a keteniminium ion intermediate to facilitate the stereoselective addition of hydrazones in the presence of K2CO3, while pyrazole ring could not be constructed under the current conditions.

Ring Expansion and 1,2-Migration Cascade of Benzisoxazoles with Ynamides: Experimental and Theoretical Studies

Demonstrated herein is an AuI-catalyzed annulation of sulfonyl-protected ynamides with substituted 1,2-benzisoxazoles for the synthesis of E-benzo[e][1,3]oxazine derivatives. The transformation involves the addition of benzisoxazole to the gold-activated ynamide, ring expansion of the benzisoxazole fragment to provide an α-imino vinylic gold intermediate, and 1,2-migration of the sulfonamide motif to the masked carbene center to deliver the respective ring-expanded benzo[e][1,3]oxazine of predominant E configuration. A trapping experiment justifies the participation of the α-imino masked gold carbene. DFT computations also support the hypothesized mechanism and rationalize the product stereoselectivity.

Er(OTf)3-catalyzed approach to 3-alkenylindoles through regioselective addition of ynamides and indoles

An efficient approach to access functionalized 3-alkenylindoles has been developed through Er(OTf)3-catalyzed addition of ynamides and indoles. A number of C-aryl substituted ynamides 7a-7k could react with indoles 6a-6s, affording the desired products 8aa-8sa, 8ab-8ak, 8bd, 8bk and 8tc in moderate to excellent yields with high regioselectivities.

Nickel-catalyzed regioselective hydroamination of ynamides with secondary amines

The first Ni(OTf)2-catalyzed hydroamination of ynamides 2 was developed by reacting with secondary amines (1 and 4). This protocol features excellent regioselectivity, a broad substrate scope of secondary aryl amines, and good functional group tolerance for ynamides. Using this method, a variety of substituted ethene-1,1- diamine compounds were prepared in moderate to excellent yields with high regioselectivities.

DIBENZOTHIOPHENE SALT AS ALKYNYLATING AND CYANATING AGENT

The present invention describes a new alkynylation and cyanation agent, as well as its preparation and use to introduce nitrile (cyano) or alkyne groups into chemical target molecules by means of an electrophilic reaction. To enable an electrophilic reaction, the chemical backbone of dibenzothiophene was used.

Biogenic synthesis of Pd-nanoparticles using Areca Nut Husk Extract: a greener approach to access α-keto imides and stilbenes

An eco-friendly green method for a one-step synthesis of palladium nanoparticles and their synthetic utility are reported. Phytochemicals like amines, alcohols, and phenols present in the Areca Nut Husk extract facilitate the reduction of Pd(ii) to Pd(0). The phytochemicals serve as stabilising agents and ligands for palladium reduction and the need for an external ligand is avoided. The Field Emission Scanning Electron Microscopy and Transmission Electron Microscopy of newly synthesized palladium nanoparticles revealed a spherical morphology. The catalytic activity of the nanoparticles was tested for 1,2-difunctionalization of ynamides, Heck coupling, denitrogenative coupling of phenylhydrazine and C-H arylation of indole. Moreover, catalyst recyclability, control experiments, mechanistic elucidation, and gram-scale synthesis are elaborated.