1005500-75-3

Basic information

• Product Name: N-(methyl)-N-(p-toluenesulfonyl)ethynylamine
• Synonyms: N-(methyl)-N-(p-toluenesulfonyl)ethynylamine
• CAS NO: 1005500-75-3
• Molecular Weight: 209.269
• Mol File: 1005500-75-3.mol

Chemical Properties

• CAS DataBase Reference: N-(methyl)-N-(p-toluenesulfonyl)ethynylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(methyl)-N-(p-toluenesulfonyl)ethynylamine(1005500-75-3)
• EPA Substance Registry System: N-(methyl)-N-(p-toluenesulfonyl)ethynylamine(1005500-75-3)

Safety Data

• Hazardous Substances Data: 1005500-75-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(methyl)-N-(p-toluenesulfonyl)ethynylamine is used as a reagent in organic synthesis for its ability to react with various substrates, facilitating the creation of a wide array of organic compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N-(methyl)-N-(p-toluenesulfonyl)ethynylamine is utilized as a key intermediate in the synthesis of drug molecules, contributing to the development of new medications.
Used in Agrochemical Production:
Similarly, in agrochemicals, this compound serves as an essential component in the synthesis of various agrochemical products, playing a role in the production of pesticides and other agricultural chemicals.
Used in the Synthesis of Fine Chemicals:
N-(methyl)-N-(p-toluenesulfonyl)ethynylamine is also employed in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, flavors, and specialty chemicals.

Upstream product

• 872349-00-3 N,4-dimethyl-N-((trimethylsilyl)ethynyl)benzenesulfonamide 
• 156-59-2 cis-1,2-Dichloroethylene 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 79-00-5 1,1,2-trichloroethane 
• 75-35-4 1,1-Dichloroethylene 
• 1007597-63-8 N-(methyl)-N-(p-toluenesulfonyl)-2-(triisopropylsilyl)ethynylamine 

Downstream Products

• 1303612-04-5 C₁₀H₁₀INO₂S 
• 1303612-05-6 C₁₂H₁₂INO₃S 
• 1303612-11-4 C₁₇H₂₁NO₃SSi 
• 1268600-17-4 N-(methyl)-N-(p-toluenesulfonyl)-5-butyl-3-hydroxy-2-methylamine 
• 1005500-76-4 N-(methyl)-N-(p-toluenesulfonyl)-2-methylethynylamine 

Relevant articles and documents

Regio- and Stereo-Selective Intermolecular Hydroamidation of Ynamides: An Approach to (Z)-Ethene-1,2-Diamides

An efficient intermolecular trans-selective β-hydroamidation of ynamides to furnish a series of (Z)-ethene-1,2-diamide derivatives with excellent regio- and stereo-selectivities is described. The trans-β-addition reactions have been illustrated for a wide range of substrates and proceeded under basic reaction conditions using readily available materials in the absence of a transition-metal catalyst. The synthetic approach to these novel (Z)-ethene-1,2-diamide derivatives paves the way for further exploration of their synthetic application.

Regio- and Stereoselective Hydrophosphorylation of Ynamides: A Facile Approach to (Z)-β-Phosphor-Enamides

The first trans-selective β-hydrophosphorylation of ynamides, which provides a facile approach to (Z)-β-phosphor-enamide derivatives in moderate to excellent yields and with excellent regio- and stereoselectivity, is described. This transition-metal-free reaction is featured with operationally simple procedure, mild reaction conditions, readily available starting materials, broad substrate scope and good functional-group tolerance. It is noted that the (Z)-β-phosphor (V)-enamides can be prepared from the oxidation of the corresponding phosphine derivatives or the direct β-hydrophosphorylation of ynamides with diphenylphosphine oxide. In addition, cis-trans isomerization of (Z)-β-phosphor (V)-enamides can be easily realized to furnish the corresponding (E)-β-phosphor (V)-enamides. This advantageous feature enables the preparation of (Z)-β-phosphor (V)-enamides as well as (E)-β-phosphor (V)-enamides from the same starting materials. (Figure presented.).

Copper-Catalyzed Synthesis of Terminal vs. Fluorine-Substituted N-Allenamides via Addition of Diazo Compounds to Terminal Ynamides

A copper-mediated coupling reaction between ynamides and diazo-compounds to produce N-allenamides is reported for the first time. This method enables facile and rapid access to terminal N-allenamides by using commercially available TMS-diazomethane with w

Catalytic Asymmetric Hydroacyloxylation/Ring-Opening Reaction of Ynamides, Acids, and Aziridines

A highly enantioselective three-component reaction of ynamides with carboxylic acids and 2,2′-diester aziridines has been realized by using a chiral N,N′-dioxide/Ho(OTf)3 complex as a Lewis acid catalyst. The process includes the formation of an α-acyloxyenamide intermediate through the addition of carboxylic acids to ynamides and the following enantioselective nucleophilic addition to in-situ-generated azomethine ylides induced by the chiral catalyst. A range of amino acyloxyenamides are delivered in moderate to good yields with good ee values. In addition, a possible catalytic cycle with a transition model is proposed to elucidate the reaction mechanism.

Photo-induced synthesis of β-sulfonyl imides from carboxylic acids

A photo-induced imidation process of carboxylic acids is described. Numerous carboxylic acids could convert to β-sulfonyl imides in the presence ofN-sulfonyl ynamides under visible light irradiation. Control experiments and mechanistic studies demonstrate that this imidation process involves a hydroacyloxylation/radical rearrangement cascade. This protocol represents a direct imidation method from carboxylic acids under mild conditions, with broad scope and high atom-economy.

Metal-free C8-H functionalization of quinolineN-oxides with ynamides

The metal-free C8-H functionalization of quinolineN-oxides with ynamides is unveiled for the first time by the intramolecular Friedel-Crafts-type reaction of quinolyl enolonium intermediates generated from Br?nsted acid-catalyzed addition of quinolineN-ox

Direct Synthesis of CF2H-Substituted 2-Amidofurans via Copper-Catalyzed Addition of Difluorinated Diazoacetone to Ynamides

The significance of molecules containing difluoromethyl groups is driven by their potential applications in pharmaceutical and agrochemical science. Methods for the incorporation of lightly fluorinated groups such as CF2H have been less well developed. He

Catalytic Asymmetric Three-component Hydroacyloxylation/ 1,4-Conjugate Addition of Ynamides

A highly enantioselective three-component hydroacyloxylation/1,4-conjugate addition of ortho-hydroxybenzyl alcohols, ynamides and carboxylic acids was developed under mild reaction conditions in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex, which went through in situ generated ortho-quinone methides with α-acyloxyenamides, delivering a range of corresponding chiral α-acyloxyenamides derivatives containing gem(1,1)-diaryl skeletons in moderate to good yields with excellent ee values. The scale-up experiment and further derivation showed the practicality of this catalytic system. In addition, a possible catalytic cycle and transition state model was proposed to elucidate the origin of the stereoselectivity based on X-ray crystal structure of the α-acyloxyenamide intermediate and product.

Ynamide-Mediated Thionoester and Dithioester Syntheses

A novel ynamide-mediated synthesis of thionoesters and dithioesters is described. The selective addition reactions of various monothiocarboxylic acids with ynamide furnish α-thioacyloxyenamides, which undergo transesterification with nucleophilic -OH or -SH species to afford thionoesters and dithioesters, respectively. The broad substrate scope, mild reaction conditions, and excellent yields make this method an attractive synthetic approach to thionoesters and dithioesters.

Gold-Catalyzed Oxidations of 1,3-Diynamides with C(1) versus C(3) Regioselectivity: Catalyst-Dependent Oxidative Cyclizations in the C(3) Oxidation

This work reports two distinct paths in catalytic oxidations of 1,3-diynamides with 8-methylquinoline oxide. A typical C(1) regioselectivity was observed for aryl-substituted 1,3-diyn-1-amides, whereas an unexpected C(3) regioselectivty occurred for 5-hydroxy1,3-diyn-1-amides. We focused on the C(3) oxidations of 5-hydroxy1,3-diyn-1-amides because we observed two oxidative cyclizations of the same substrates to yield 2-aminomethylenefuran-3(2H)-ones and 2-amino-4H-pyran-4-ones using AuCl3 and a cationic gold catalyst, respectively. Density functional theory calculations were performed to rationalize the C(3) regioselectivity on 5-hydroxy1,3-diyn-1-amides.