13141-38-3

Basic information

• Product Name: 2-(phenylethynyl)aniline
• Synonyms: Benzenamine, 2-(2-phenylethynyl)-
• CAS NO: 13141-38-3
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24384
• Mol File: 13141-38-3.mol
• Article Data: 47

Chemical Properties

• Melting Point: 89 °C(Solv: ethanol (64-17-5))
• Boiling Point: 359.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.42±0.10(Predicted)
• CAS DataBase Reference: 2-(phenylethynyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(phenylethynyl)aniline(13141-38-3)
• EPA Substance Registry System: 2-(phenylethynyl)aniline(13141-38-3)

Safety Data

• Hazardous Substances Data: 13141-38-3(Hazardous Substances Data)

Usage

General Description

2-(phenylethynyl)aniline is a chemical compound with the molecular formula C14H11N. It is an aromatic amine, meaning it contains both an amine and an aromatic ring in its structure. The compound is commonly used in the production of dyes and pigments due to its ability to impart vibrant and stable colors to various materials. Additionally, 2-(phenylethynyl)aniline has been studied for its potential applications in organic electronics and optoelectronics, as it exhibits properties suitable for use in devices such as organic light-emitting diodes and organic field-effect transistors. Its unique chemical structure and versatile properties make it a valuable component in various industrial and technological applications.

Upstream product

• 35010-17-4 1-nitro-2-phenylethynyl-benzene 
• 615-43-0 2-iodophenylamine 
• 536-74-3 phenylacetylene 
• 13146-23-1 copper(I) phenylacetylenide 
• 1873-77-4 tris-(trimethylsilyl)silane 
• 199277-23-1 1-azido-2-(phenylethynyl)benzene 
• 52670-38-9 2-ethynylaniline 
• 591-50-4 iodobenzene 
• 143360-93-4 N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 615-36-1 2-bromoaniline 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 143360-89-8 o-(phenylethynyl)trifluoroacetanilide 

Downstream Products

• 143360-89-8 o-(phenylethynyl)trifluoroacetanilide 
• 285991-63-1 4,6-dichloro-pyrimidine-5-carboxylic acid (2-phenylethynyl-phenyl)-amide 
• 13141-39-4 N-<2-(2-Phenylethynyl)phenyl>methanamide 
• 1103523-11-0 C₂₂H₂₁NO₂ 
• 948-65-2 2-phenyl-indole 
• 1103523-19-8 C₁₈H₁₅NO₂ 

Relevant articles and documents

Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina

A microwave-enhanced, solventless Sonogashira coupling reaction has been developed. Terminal alkynes couple with aryl or alkenyl iodide on palladium- doped alumina in the presence of triphenylphosphine and cuprous iodide to provide high yields of products. (C) 2000 Published by Elsevier Science Ltd.

Effect of solvent polarity on N-H insertion versus rearrangement of alkylidene carbenes

Alkylidene carbenes, when generated from o-aminobenzophenones and lithiated trimethylsilyldiazomethane, give a mixture of alkyne (by rearrangement) and indole (by N-H insertion). It has been found that this ratio of indole to acetylene shows a linear dependence on the polarity of the ethereal solvent.

Magnetic Cu–Schiff base complex with an ionic tail as a recyclable bifunctional catalyst for base/Pd-free Sonogashira coupling reaction

Abstract: A Cu(II)–Schiff base complex containing imidazolium ionic phase was prepared and decorated on γ-Fe2O3 magnetic nanoparticles (γ-Fe2O3@Cu(II)IL-SB) and found to be an efficient catalyst for the Pd- and base-free Sonogashira coupling reaction. The heterogeneous catalyst was characterized by FTIR spectroscopy, UV–visible spectroscopy, FE-SEM, TEM, XRD spectroscopy, EDX spectroscopy, VSM, ICP spectroscopy, and atomic absorption spectroscopy. The coupling reactions were performed using the catalyst under mild and base-free conditions, and high-to-excellent yields were obtained for a variety of substrates. The catalyst demonstrates a dual-functionality arising from metal sites and imidazolium moieties and that the later plays a base role. Reusability and stability of γ-Fe2O3@Cu(II)IL-SB were studied several times, which can be reused up to eight consecutive runs with at least reduction in catalytic activity. Also, the mechanism of this bifunctional catalytic system was thoroughly investigated. Graphic abstract: A new and efficient method has been developed for the base- and Pd-free Sonogashira cross-coupling reactions of aryl halides with phenyl acetylene using a bifunctional γ-Fe2O3@Cu(II)IL-SB catalyst with imidazolium moiety under mild conditions[Figure not available: see fulltext.].

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.

Diorganyl tellurides as substrates in Sonogashira coupling reactions under mild conditions

A new method of Sonogashira coupling reactions between diorganyl tellurides and terminal alkynes is reported. The coupling reactions are performed using Pd(dppf)Cl2 as a catalyst, CuI as a co-catalyst in the presence of K2CO3 in DMSO. The reactions are carried out at room temperature and completed within 2 h when phenyl acetylene is used as a terminal alkyne. For aliphatic terminal alkynes, such as 1-hexyne and 1-octyne, an elevated temperature and longer reaction time are needed for the completion of the reactions. This process results in good yields of Sonogashira coupling products which is applicable for diaryl, divinyl and dialkynyl tellurides but not applicable for dialkyl tellurides.