6941-73-7

Basic information

• Product Name: 2-[2,2-BIS-(1H-INDOL-3-YL)-ETHYL]-PHENYLAMINE
• Synonyms: 2-[2,2-bis(1H-indol-3-yl)ethyl]aniline
• CAS NO: 6941-73-7
• Molecular Formula: C₂₄H₂₁N₃
• Molecular Weight: 351.44
• Mol File: 6941-73-7.mol

Chemical Properties

• Boiling Point: 592.8°C at 760 mmHg
• Flash Point: 347.9°C
• Appearance: /
• Density: 1.282g/cm³
• Vapor Pressure: 5.04E-14mmHg at 25°C
• Refractive Index: 1.766
• CAS DataBase Reference: 2-[2,2-BIS-(1H-INDOL-3-YL)-ETHYL]-PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2,2-BIS-(1H-INDOL-3-YL)-ETHYL]-PHENYLAMINE(6941-73-7)
• EPA Substance Registry System: 2-[2,2-BIS-(1H-INDOL-3-YL)-ETHYL]-PHENYLAMINE(6941-73-7)

Safety Data

• Hazardous Substances Data: 6941-73-7(Hazardous Substances Data)

Usage

General Description

2-[2,2-BIS-(1H-INDOL-3-YL)-ETHYL]-PHENYLAMINE, also known as apeginin, is a chemical compound composed of two indole rings attached to an ethyl group, which in turn is connected to a phenylamine moiety. It is a synthetic organic compound that has been studied for its potential pharmacological properties, such as its anti-inflammatory and antioxidant effects. Apeginin may also have potential applications in the field of medicine and drug development due to its unique chemical structure and potential therapeutic properties. However, more research is needed to fully understand its mechanisms of action and potential uses.

InChI:InChI=1/C24H21N3/c25-22-10-4-1-7-16(22)13-19(20-14-26-23-11-5-2-8-17(20)23)21-15-27-24-12-6-3-9-18(21)24/h1-12,14-15,19,26-27H,13,25H2

Upstream product

• 120-72-9 indole 
• 6637-10-1 2,3-dihydro-1H,1'H-[2,3']biindolyl 
• 536-74-3 phenylacetylene 
• 1896-62-4 (E)-benzalacetone 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 28035-59-8 2,3-dihydro-1'H-[2,3']biindolyl-1-carboxylic acid ethyl ester 
• 15582-86-2 methyl o-nitrostyrylcarbamate 
• 1969-73-9 (2-nitrophenyl)acetaldehyde 
• 180910-53-6 1-hydroxy-N_b-methoxycarbonyltryptamine 
• 180910-54-7 1-hydroxy-Nb-trifluoroacetyltryptamine 
• 7479-22-3 3,3'-(o-nitrophenethylidene)di-indole 
• 88048-51-5 ortho -2 ethyl, ethoxy carbanilide 
• 1484-27-1 3-bromoindole 
• 16990-74-2 3-hydroxy-3-methyloxindole 

Downstream Products

• 120-72-9 indole 
• 65439-77-2 2,3'-(o-aminophenethylidene)di-indole 
• 120499-36-7 2-(2,2-di-indol-3-yl-ethyl)-N,N-dimethyl-aniline 

Relevant articles and documents

Br?nsted acidic ionic liquid–catalyzed tandem trimerization of indoles: An efficient approach towards the synthesis of indole 3,3′-trimers under solvent-free conditions

We have observed the role of 1-butane sulfonic acid-3-methylimidazolium tosylate, [BSMIM]OTs, as an organocatalyst for the tandem type trimerization of indoles to synthesize indole 3,3′-trimers under neat conditions. Using this developed protocol synthesis of indole trimers with various substituted indoles, which are biologically important, has been reported. From the control experiments and literature, a possible mechanism has been proposed via the generation of indolinium cation in the presence of the ionic liquid catalyst. The catalyst has been recycled for several times. The significant advantages of our methodology are clean reaction with very short time, no chromatography for purification, commercially available substrates, neat reaction conditions, and in the absence of metal. Using the protocol, the MDM2-p53 inhibitor has been synthesized in gram scale with high yield.

B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes: An approach toward bis(indolyl)alkanes

The first example of the metal-and solvent-free B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes was disclosed. Both N-H and N-protected indoles were tolerated, leading to a wide spectrum of versatile bis

Sc(OTf) 3 -Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles

Oligomerization of substituted indoles and N -methylindoles was investigated in the presence of catalytic amounts of scandium triflate in dichloromethane. Two types of indole oligomer, 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles were obtained based on the substituent on indole ring. This study constitutes the first example of Sc(OTf) 3 -catalyzed oligomerization of indoles and gave good yield of 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles..

Thermodynamics and kinetics of indole oligomerization in 0.5molL -1 aqueous sulfuric acid: Evaluation of some temperature-dependant parameters

Indole is present in a wide variety of natural compounds with physiological activities, as well as it is a very important intermediate in medicinal and industrial chemistry. For this reason, the evaluation of indole protonation, oligomerization equilibria and the study of the kinetics of dimer and trimer formation in diluted sulfuric acid at various temperatures are of paramount importance because of their practical and scientific implications. Here, we calculate the protonation equilibria by using the literature titration data together with a quantum chemical computational approach, in order to obtain reliable pKa value of indole from 288 to 313K. Starting from these calculations, we are able to measure the oligomerization equilibrium constants of indole, their kinetic constants, whose values are dependent of indole pK a, at different temperatures. Enthalpy and entropy of the reactions are calculated by means of Van't Hoff equation, while the activation parameters of Eyring-Evans-Polanyi equation are evaluated for the whole kinetic constants. Copyright

Solvent-free Br?nsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols

A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Br?nsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr's nucleophilicity and electrophilicity scales.

Acid-catalyzed reactions of 3-hydroxy-2-oxindoles with electron-rich substrates: Synthesis of 2-oxindoles with all-carbon quaternary center

A Lewis acid catalyzed reaction of in situ generated 2H-indol-2-one (9) with various 2π and other electron-rich substrates has been developed. A variety of electron-rich substrates such as allyl/methallyltrimethylsilane, phenylacetylene, styrenes, acetophenone, and indoles have been used. The methodology provides a straightforward approach for the synthesis of 2-oxindoles with an all-carbon quaternary center at the pseudobenzylic position.

A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and β-nitrostyrenes, via an unprecedented reaction sequence

A six-step one-pot reaction was designed for synthesizing homodimeric 7-phenylindolo[3,2-a]carbazoles from 1H-indoles and β-nitrostyrenes, in the presence of SnCl2·2H2O. The reactions proceeded under very mild conditions and the desi

Hf(Otf)4-catalyzed 1,4-addition reactions of indole to enone in the presence of meso and chiral pyridine-diamine ligands

Hf(OTf)4-catalyzed 1,4-addition reactions of indole to enones in the presence of pyridinediamine are described. Although a dimer and a trimer of indole were produced under the Hf(OTf)4 catalyzed reaction conditions of indole, the add

Nucleophilic substitution reaction at the 1-position of 1-hydroxytryptamine and -tryptophan derivatives

A novel nucleophilic substitution reaction at the 1-position of indole nucleus was discovered by reacting 1-hydroxytryptamine and -tryptophan derivatives with indoles in 85% formic acid yielding 1-(indol-3-yl)indoles. Their structures were determined by X-Ray crystallographic analysis and chemical correlations. An SN2 mechanism on the indole nitrogen (1-position) is proposed.

Therapeutic and diagnostic ligand systems comprising transport molecule binding properties and medicaments containing the same

The invention relates to transport molecule binding ligand compounds which comprise a therapeutically and/or diagnostically active substance and a carrier molecule-affine substance with a high association constant to the carrier molecule. The invention also relates to medicaments containing these ligand compounds and to diagnostic kits.