6637-10-1

Basic information

• Product Name: 2,3'-Bi-1H-indole,2,3-dihydro-
• Synonyms: Indoline,2-indol-3-yl- (6CI,7CI,8CI); 2-(3-Indolyl)indoline;3-(2,3-Dihydro-1H-indol-2-yl)-1H-indole; NSC 52361
• CAS NO: 6637-10-1
• Molecular Formula: C16H14 N2
• Molecular Weight: 234.301
• Mol File: 6637-10-1.mol

Chemical Properties

• CAS DataBase Reference: 2,3'-Bi-1H-indole,2,3-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3'-Bi-1H-indole,2,3-dihydro-(6637-10-1)
• EPA Substance Registry System: 2,3'-Bi-1H-indole,2,3-dihydro-(6637-10-1)

Safety Data

• Hazardous Substances Data: 6637-10-1(Hazardous Substances Data)

Usage

Classification

Biaryl compound, derivative of indole

Biological Activities

Anti-inflammatory
Anti-cancer
Anti-bacterial

Applications

Synthesis of pharmaceuticals
Synthesis of organic compounds
Fluorescent probe in biological imaging
Potential anti-tumor agent

Upstream product

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• 1016-47-3 N-Acetyltryptamine 
• 1484-27-1 3-bromoindole 

Relevant articles and documents

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

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.

Nucleophilic substitution reaction on the nitrogen of indole nucleus: A novel synthesis of 1-aryltryptamines

1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nitrogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles,

Nucleophilic substitution reaction on the nitrogen of indole nucleus: Formation of 1-(indol-3-yl)indoles upon reaction of 1-hydroxyindoles with indole in formic acid

1-(Indol-3-yl)indoles are obtained in excellent to good yields by the reaction of 1-hydroxyindoles with indole in 85% formic acid. Their structures are determined by X-Ray crystallographic analysis and chemical correlations. The unprecidented SN2 mechanis

The reactions of nitrones with indoles

The reaction of nitrones with various indole derivatives has been studied. When the reaction was promoted by C1SiMe3, the isolated products were 3,3'-diindolylalkanes. With HC1 as the activating reagent, 3- indolylhydroxylamines were isolated. The diastereoselectivity of this condensation with a nitrone derived from cysteine was investigated. A method for the introduction of an alkylhydroxylamino group onto position 2 of indole, the synthesis of three natural 3,3'-diindolylalkanes and of non- symmetric diindolylalkanes are also reported. (C) 2000 Elsevier Science Ltd.

Neat formic acid: An excellent N-formylating agent for carbazoles, 3- alkylindoles, diphenylamine and moderately weak nucleophilic anilines

Neat formic acid alone efficiently N-formylates carbazoles, 3- alkylindoles, diphenylamine and even moderately weak nucleophilic anilines to furnish the corresponding N-formyl derivatives in 72-87% yields.

Intermolecular trapping by indole of a spiroindolenine intermediate formed during the Bischler-Napieralski cyclisation of N-acetyltryptamine

The Bischler-Napieralski cyclisation of N-acetyltryptamine (1a) in the presence of indole (15) affords a moderate yield of the diastereomeric spiroindolines 9 and 10 suggesting the intermediacy of a spiroindolenine 2a in this reaction. Evidence is provided to show that the minor reaction products 2-methyltryptamine (11), tris-(3-indolyl)methane (12) and 6-[(o-aminophenyl) methyl]-5,11-dihydroindolo[3,2-b]carbazole (13) are derived from the spiroindolines 9 and 10.

SYNTHESIS AND CHARACTERIZATION OF NEW INDOLE TRIMERS AND TETRAMERS

A new method has been achieved to synthesize indole trimers and tetramers starting from indoles and 3-bromoindoles.Unusual open and cyclic trimers have been isolated and characterized, and the mechanism of formation is proposed.

Electrophilic Substitution of Indoles: Part IV . Addition and Annulation Reactions with Mesityl Oxide

The electrophilic substitution of 2- and 3-methylindoles with mesityle oxide has resulted in the synthesis of two novel heterocyclic systems (V) and (VIII).The structures of these products have been settled from the detailed spectral analysis including 13C-NMR.The structure of compound (VIII) has been further confirmed by single crystal X-ray analysis.