124643-45-4

Usage

Uses

Used in Organic Synthesis:
2-(p-tolylethynyl)aniline is used as a precursor in organic synthesis for the production of various pharmaceuticals, dyes, and polymer materials. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of a wide range of compounds.
Used in Optoelectronic Devices:
In the field of organic electronics, 2-(p-tolylethynyl)aniline is utilized as a building block in the synthesis of organic light-emitting diodes (OLEDs) and other optoelectronic devices. Its electronic properties contribute to the performance and efficiency of these devices, enhancing their light-emitting capabilities and overall functionality.
Used in Materials Science:
2-(p-tolylethynyl)aniline's structural and electronic properties also make it a promising candidate for applications in materials science. It can be incorporated into the development of new materials with specific properties, such as improved conductivity or light-emitting characteristics, broadening its utility across various industries.

Upstream product

• 52670-38-9 2-ethynylaniline 
• 29540-83-8 p-tolyl triflate 
• 615-43-0 2-iodophenylamine 
• 766-97-2 4-n-methylphenylacetylene 
• 624-31-7 4-tolyl iodide 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 106-38-7 para-bromotoluene 
• 62-53-3 aniline 
• 95-53-4 o-toluidine 
• 38175-73-4 1-bromo-2-(p-tolylethynyl)benzene 
• 40164-42-9 1-[2-(4-methylphenyl)ethynyl]-2-nitrobenzene 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 

Downstream Products

• 55577-25-8 2-(4-methylphenyl)-1H-indole 
• 55164-81-3 3-(4-methylphenyl)quinolin-2(1H)-one 
• 60473-07-6 1H-indazole-3-yl(4-methylphenyl)methanone 
• 90828-09-4 (E)-3-(4-methylbenzylidene)indolin-2-one 
• 1236003-88-5 (Z)-N,N-dimethyl-4-(4-methylbenzylidene)-4H-benzo[d][1,3]thiazin-2-amine 
• 1264617-00-6 1-[methoxy(phenyl)methyl]-2-p-tolylindole-3-carboxylic acid methyl ester 
• 1351667-52-1 N,N-diallyl-1-methanesulfonyl-2-(4-methyphenyl)indol-3-amine 
• 1351667-53-2 N-allyl-N-methyl-1-methanesulfonyl-2-(4-methylphenyl)-indol-3-amine 
• 1351667-54-3 1-methanesulfonyl-2-(4-methylphenyl)-3-(1-piperidinyl)-indole 
• 1351667-55-4 N-butyl-1-methanesulfonyl-2-(4-methylphenyl)-N-(4-penten-1-yl)indol-3-amine 
• 1351667-31-6 N-(2-(p-tolylethynyl)phenyl)methanesulfonamide 
• 1361452-41-6 11-chloro-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]quinoline 
• 1361452-25-6 11-allyl-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]quinoline 

Relevant academic research and scientific papers

Copper-Catalyzed Aerobic Oxidative Cyclization of 2-Alkynylanilines with Nitrosoarenes: Synthesis of Organic Solid Mechanoluminescence Compounds of 4-Oxo-4 H-cinnolin-2-ium-1-ide

An efficient Cu(I)/DMAP/air system for the one-pot synthesis of 4-oxo-4H-cinnolin-2-ium-1-ides, which are often difficult to prepare by traditional routes from substituted 2-alkynylanilines and nitrosoarenes, was developed. These 4-oxo-4H-cinnolin-2-ium-1-ides have practical applications as mechanoluminescent materials. Preliminary mechanistic experiments were performed, and a plausible mechanism for this tandem process is proposed. The use of an inexpensive copper catalyst and molecular oxygen as the oxygen source and the oxidant make this an attractive green protocol with potential synthetic applications.

Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones

Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.

Copper(I)-Mediated Cascade Annulation via Dual C-H/C-H Activation: Access to Benzo[a]carbazolic AEEgens

A Cu(I)-mediated cascade cyclization/annulation of unprotectedo-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C-N and two C-C bonds to deliver fused benzo[a]carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485-502 nm with a large Stokes shift and fluorescence lifetime of ～17 ns. The annulated3aadisplays AEE behavior in the ethanol/hexane system and possesses marigold-flower-like morphology at the aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular fluorescence depicts cell imaging applicability.

Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds

Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C?C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient e

Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides

N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.

Gold(I)-Catalyzed Reactions between N-(o-Alkynylphenyl)imines and Vinyldiazo Ketones to Form 3-(Furan-2-ylmethyl)-1 H-indoles via Postulated Azallyl Gold and Allylic Cation Intermediates

This work describes gold-catalyzed additions of vinyldiazo ketones to N-(o-alkynylphenyl)imines to yield 3-(furan-2-ylmethyl)-1H-indoles involving skeletal rearrangement; these new catalytic reactions are applicable to a wide range of substrates. We postu

Cascade Reactions Assisted by Microwave Irradiation: Ultrafast Construction of 2-Quinolinone-Fused γ-Lactones fromN-(o-Ethynylaryl)acrylamides and Formamide

An ultrafast (10 s) methodology to construct novel highly functionalized 2-quinolinones fromN-(o-ethynylaryl)acrylamides (1,7-enynes) is described for the first time. Microwave irradiation enabled the ultrafast synthesis of 2-quinolinone-fused γ-lactones from Fenton’s reagents in formamide. After six key consecutive reactions, including a diastereoselective step, 2-quinolinone-fused γ-lactones were obtained in good overall yield (up to 46%; 10 s).

Asymmetric Synthesis of 3-Methyleneindolines via Rhodium(I)-Catalyzed Alkynylative Cyclization of N-(o-Alkynylaryl)imines

The first asymmetric synthesis of 3-methyleneindolines from alkynyl imines has been developed via a rhodium-catalyzed tandem process: regioselective alkynylation of the internal alkynes and subsequent intramolecular addition to the imines. The reaction pr

An expedient route to tricyanovinylindoles and indolylmaleimides fromo-alkynylanilines utilising DMSO as a one-carbon synthon

A Pd(ii)/Cu(ii) catalysed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a one-carbon synthon. The reaction proceedsviathe construction of 2-aryl-3-formyl indole followed by sequential addition of malononitrile and a CN resulting

Gold-Catalyzed Cascade and Divergent Synthesis of Indolobenzazepines and Indoloquinolines from Nitrogen-Tethered 1,8-Diynes

We describe the divergent construction of two nitrogen-containing polycyclic systems by gold-catalyzed cycloisomerizations. The gold-catalyzed cascade hydroamination and 7-endo-dig-selective cycloisomerization of nitrogen-tethered 1,8-diynes yielded indol