27393-85-7

Usage

Uses

Used in Pharmaceutical and Organic Synthesis:
2-(1H-indol-3-yl)-1H-indole is used as a building block in the synthesis of complex organic molecules, particularly in the pharmaceutical industry, due to its unique molecular structure and properties. It contributes to the development of new drugs and organic compounds with potential therapeutic applications.
Used in Fluorescence-based Analytical Techniques and Assays:
Leveraging its fluorescence properties, 2-(1H-indol-3-yl)-1H-indole is employed in fluorescence-based analytical techniques and assays across various scientific fields. It serves as a valuable tool for detecting and analyzing target molecules, enhancing the sensitivity and specificity of these assays.

Upstream product

• 120-72-9 indole 
• 1484-27-1 3-bromoindole 
• 180910-54-7 1-hydroxy-Nb-trifluoroacetyltryptamine 
• 180910-53-6 1-hydroxy-N_b-methoxycarbonyltryptamine 
• 5339-85-5 2-aminophenethyl alcohol 
• 15121-84-3 2-nitro-benzeneethanol 
• 88-72-2 1-methyl-2-nitrobenzene 
• 573970-34-0 (R,R)-(-)-bis(α-methylbenzyl)aminoacetaldehyde dimethyl acetal 

Downstream Products

• 111296-91-4 7,12-dihydropyrido<3,2-b;5,4-b'>diindole 

Relevant academic research and scientific papers

Convenient and scalable process for the preparation of indole via raney nickel-catalyzed hydrogenation and ring closure

An efficient and practical method for the synthesis of indole as a key starting material for many useful chemicals is described. Using 2-nitrotoluene as starting material, hydroxymethylation with formaldehyde under alkaline conditions gave 2-(2-nitrophenyl) ethanol on a large scale. Raney Ni catalyst was used for both reduction of the nitro group as well as for the indole formation. The overall yield was 78% from 2-nitrotoluene. Copyright

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.

Studies on the Lewis acid mediated cleavage of α-aminoacetals: Synthesis of novel 1,2-aminoethers, and evidence for α-alkoxy aziridinium ion intermediates

The nucleophilic cleavage of α-amino acetals induced by TMSOTf can be used to prepare a wide range of substituted 1,2-aminoethers. In particular, organometallic reagents, N-heterocycles, and enamines all react efficiently to give products in good yield. In appropriate cases, good levels of stereocontrol are possible, but this is very dependent on the nature of the nucleophile and the substrate, with diethylzinc proving particularly effective across a range of substrates. The degree of stereocontrol can be used to infer the nature of the reactive intermediates involved in the reaction. With diethylzinc, it is most likely that the reaction proceeds by coordination of the nucleophile to the amino group followed by transfer of an ethyl group to an α-oxocarbenium ion. With non-coordinating nucleophiles, the stereochemical outcome can be rationalised in terms of addition to the possible α-alkoxy aziridinium ion intermediates.

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,

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.

SYNTHESIS AND SPECTROSCOPIC CHARACTERISTICS OF 2,3'-BIINDOLYLS AND 2,2'-INDOLYLPYRROLES

A general and selective method has been achieved to synthesize 2,3'-biindolyls and 2,2'-indolylpyrroles through an acid catalyzed reaction of 3-bromoindoles with indoles or pyrroles.I.R., (1)H-NMR, (13)C-NMR and MS data of the dimers are also reported.