14235-81-5

Usage

Uses

Used in Chemical Synthesis:
4-Ethynylaniline is used as a key component in the synthesis of various organic compounds, such as N-methyliminodiethyl 4-(4-ethynylphenyliminomethyl) benzeneboronate. It plays a crucial role in the formation of these complex molecules, contributing to their unique properties and potential applications.
Used in the Preparation of Acetylene Ligands:
4-Ethynylaniline is utilized in the preparation of acetylene ligands, such as HC2-NDI (NDI = 1,4,5,8-naphthalenediimide). These ligands are essential in various chemical reactions and can be used to modify the properties of metal complexes, enhancing their performance in catalysis and other applications.
Used in the Synthesis of Indoles:
4-Ethynylaniline serves as an alkyne component in the synthesis of indoles from nitroarenes in the presence of a palladium-phenantroline catalyst. Indoles are important organic compounds with a wide range of applications, including pharmaceuticals, agrochemicals, and materials science.
Used in Surface Functionalization:
4-Ethynylaniline is employed in the surface functionalization of multi-walled carbon nanotubes (MWNTs) and graphene, which can significantly impact their thermal behavior. This functionalization can improve the properties of these materials, making them more suitable for various applications, such as energy storage, electronics, and composite materials.

Reaction

4-Ethynylaniline, also known as p-ethynylaniline, is a terminal alkyne. Its synthesis using 2-methyl-3-butyn-2-ol (MEBYNOL) has been reported. The transition metal catalyzed polymerization of 4-ethynylaniline to afford poly(4-ethynylaniline) has been reported.[3]The impact of the surface functionalization with 4-ethynylaniline on the thermal behavior of multi-walled carbon nanotubes (MWNTs) and graphene has been investigated.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 5818, 1994 DOI: 10.1021/jo00098a051

InChI:InChI=1/C8H7N/c1-2-7-3-5-8(9)6-4-7/h1,3-6H,9H2

Upstream product

• 937-31-5 (4-Nitrophenyl)acetylene 
• 75867-39-9 4-trimethylsilylethynyl aniline 
• 82815-75-6 <4-(4-aminophenyl)>-2-methyl-3-butyn-2-ol 
• 158074-65-8 4-(4-aminophenyl)-2-methyl-3-butyn-2-ol trifluoroacetamide 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 540-37-4 p-aminoiodobenzene 
• 74-86-2 acetylene 
• 35447-78-0 2,3-dibromo-3-(4-nitro-phenyl)-propionic acid 
• 1453814-00-0 tert-butyl (4-(3-methyl-3-((2-nitrobenzyl)oxy)but-1-yn-1-yl)phenyl)carbamate 
• 64-18-6 formic acid 
• 14989-91-4 4-ethynylphenyl azide 
• 90050-69-4 α,α-dibromo-4-nitroethylbenzene 
• 100-12-9 4-ethylnitrobenzene 
• 13161-29-0 p-nitrocinnamyl bromide 

Downstream Products

• 28000-04-6 α-Brom-p-amino-styrol 
• 40101-59-5 2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione 
• 19368-13-9 N-(Acetylphenyl)-2-carboxybenzamide 
• 73819-75-7 2-(4-ethynylphenyl)isoindoline-1,3-dione 
• 73819-77-9 N-(4-Ethynyl-phenyl)-phthalamic acid 
• 91511-84-1 p-(5-methyl-5-hydroxy-1,3-hexadiynyl)aniline 
• 119754-26-6 dimethyl 4-(4-aminophenylethynyl)-2,6-pyridinedicarboxylate 
• 119984-85-9 4-(2-(4-aminophenyl)ethynyl)benzonitrile 
• 119984-87-1 methyl 4-((4-aminophenyl)ethynyl)benzoate 
• 135043-09-3 4-(4-Methanesulfonyl-phenylethynyl)-phenylamine 
• 110175-16-1 p-amino-p'-nitrodiphenylhexatriyne 
• 119984-86-0 p-amino-p'-cyanodiphenylbutadiyne 
• 106967-38-8 tetra(tert-butyl) 2,2',2'',2'''-[[4-[(4-aminophenyl)ethynyl]pyridine-2,6-diyl]bis(methylenenitrilo)]tetrakisacetate 
• 123770-68-3 4-((4-aminophenyl)ethynyl)acetophenone 

Relevant academic research and scientific papers

Ammonia borane dehydrogenation and selective hydrogenation of functionalized nitroarene over a porous nickel-cobalt bimetallic catalyst

The hydrolysis of ammonia borane is a promising strategy for hydrogen energy exploration and exploitation. The in situ produced hydrogen could be directly utilized in hydrogenation reactions. In this work, a bimetallic nickel-cobalt material with porous structure was developed through the pyrolysis of ZIF-67 incorporated with Ni ions. Through the introduction of Ni(NO3)2 as an etching agent, the ZIF-67 polyhedrons were transformed into hollow nanospheres, and further evolved into irregular nanosheets. The bimetallic NiCo phase was formed after pyrolysis in a nitrogen atmosphere at high temperature, with the decomposition and release of organic ligands as gaseous molecules under flowing nitrogen. The obtained bimetallic NiCo porous materials show superior catalytic performance towards hydrolytic dehydrogenation of ammonia borane, thereby nitrobenzene with reducible functional groups can be reduced with high selectivity to the corresponding aniline.

Chemoselective hydrogenation of nitroarenes catalyzed by cellulose-supported Pd NPs

Cellulose-supported palladium nanoparticles (NPs) were prepared by straightforward deposition of metal NPs on modified cellulose. The catalyst exhibited excellent catalytic activity and selectivity in room-temperature hydrogenation of various nitroarenes to arylamines under atmospheric hydrogen pressure in neat water without any additives. High chemoselectivity was also achieved in the hydrogenation of substituted nitroarenes with multiple reducible groups. The catalyst can be recycled by simple centrifugation and reused for at least 4 times without significant decline of yields.

Diruthenium phenylacetylide complexes bearing para -/ meta -amino phenyl substituents

Presented herein is the synthesis and characterization of four diruthenium(II,III) compounds of formulas Ru2(Xap) 4(C≡C-C6H4-4-NH2) (Xap is 2-anilinopyridinate, 1a; and 2-(3,5-dimethoxy)anilinopyridinate, 1b) and Ru 2(Xap)4(C≡C-C6H4-3-NH 2) (2a/2b). X-ray structural studies of compounds 1b and 2a revealed minimal changes in the coordination sphere of the Ru2 core. Voltammetric measurements showed that compounds 1 exhibit three one-electron redox processes: a reversible reduction of Ru2, a reversible oxidation of Ru2, and a quasi-reversible oxidation of an amino group. Compounds 2 display the same Ru2-based redox processes but not the -NH2 oxidation. Compounds 1a/1b were successfully converted to the corresponding diazonium salts [Ru2(Xap)4-(C≡C-C 6H4-4-N2)](BF4) (3a/3b) via oxidation by nitrosonium tetrafluoroborate, which was generated in situ from t-BuONO and BF3. However, the attempt to convert compounds 2 to the corresponding diazonium salts was unsuccessful. DFT calculations of model compounds were performed to rationalize some unusual structural and electrochemical characteristics observed for compounds 1/2.

Development of a Pre-assembled Through-Bond Energy Transfer (TBET) Fluorescent Probe for Ratiometric Sensing of Anticancer Platinum(ll) Complexes

Fluorescence microscopy has emerged as an attractive technique to probe the intracellular processing of Pt-based anticancer compounds. Herein, we reported the first through-bond energy transfer (TBET) fluorescent probe NPR1 designed for sensitive detectio

Selective hydrogenation of nitroarenes to aminoarenes using a MoO:X-modified Ru/SiO2 catalyst under mild conditions

Modification of Ru/SiO2 with metal oxides (MoOx, WOx, and ReOx) improved the activity and selectivity in the hydrogenation of 3-nitrostyrene to 3-aminostyrene under mild conditions such as 0.3 MPa H2, 303 K, and no solvent. Ru-MoOx/SiO2(Mo/Ru = 1/2) catalyst was applicable to various substituted nitroarenes, providing the corresponding substituted aminoarenes in high yields (85-99%).

A study on the electro-oxidation and electropolymerization of a new OPE linear molecule by EQCM and in situ FTIR spectroelectrochemistry

A novel symmetric conjugated oligo(phenylene-ethynylene) (OPE) linear molecule (1,4-bis(4-aminophenylethynyl)benzene); BAB) was synthesized by Sonogashira cross-coupling reactions. The structure and purity of the compound were confirmed by 1H N

Using the hydrogen and oxygen in water directly for hydrogenation reactions and glucose oxidation by photocatalysis

Direct utilization of the abundant hydrogen and oxygen in water for organic reactions is very attractive and challenging in chemistry. Herein, we report the first work on the utilization of the hydrogen in water for the hydrogenation of various organic compounds to form valuable chemicals and the oxygen for the oxidation of glucose, simultaneously by photocatalysis. It was discovered that various unsaturated compounds could be efficiently hydrogenated with high conversion and selectivity by the hydrogen from water splitting and glucose reforming over Pd/TiO2 under UV irradiation (350 nm). At the same time, glucose was oxidated by the hydroxyl radicals from water splitting and the holes caused by UV irradiation to form biomass-derived chemicals, such as arabinose, erythrose, formic acid, and hydroxyacetic acid. Thus, the hydrogen and oxygen were used ideally. This work presents a new and sustainable strategy for hydrogenation and biomass conversion by using the hydrogen and oxygen in water.

Phosphorus-Doped and Lattice-Defective Carbon as Metal-like Catalyst for the Selective Hydrogenation of Nitroarenes

We report carbon can be activated as metal-like hydrogenation catalyst for the selective hydrogenation of nitroarenes. Using DFT calculations we demonstrated the combination of P dopant and lattice defect in carbon can cause significant electron delocaliz

Cobalt nanoparticles encapsulated in nitrogen-doped carbon for room-temperature selective hydrogenation of nitroarenes

Here, we report cobalt nanoparticles encapsulated in nitrogen-doped carbon (Co@NC) that exhibit excellent catalytic activity and chemoselectivity for room-temperature hydrogenation of nitroarenes. Co@NC was synthesized by pyrolyzing a mixture of a cobalt

One-pot synthesis of monosubstituted aryl(hetaryl)acetylenes by direct introduction of the C≡CH residue into arenes and hetarenes

A convenient one-pot synthesis of aryl(hetaryl)acetylenes by cross-coupling of aryl(hetaryl)iodides with acetylene in presence of PdCl2(Ph 3)2, CuI and K2CO3 in DMF has been developed.