102241-69-0

Basic information

• Product Name: 3-[1H-indol-3-yl(thiophen-2-yl)Methyl]-1H-indole
• Synonyms: 3-[1H-indol-3-yl(thiophen-2-yl)Methyl]-1H-indole;3,3'-(thiophen-2-ylmethanediyl)bis(1H-indole)
• CAS NO: 102241-69-0
• Molecular Formula: C21H16N2S
• Molecular Weight: 328.43014
• Mol File: 102241-69-0.mol
• Article Data: 90

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-[1H-indol-3-yl(thiophen-2-yl)Methyl]-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[1H-indol-3-yl(thiophen-2-yl)Methyl]-1H-indole(102241-69-0)
• EPA Substance Registry System: 3-[1H-indol-3-yl(thiophen-2-yl)Methyl]-1H-indole(102241-69-0)

Safety Data

• Hazardous Substances Data: 102241-69-0(Hazardous Substances Data)

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 120-72-9 indole 
• 925-90-6 ethylmagnesium bromide 
• 52670-38-9 2-ethynylaniline 
• 615-43-0 2-iodophenylamine 
• 39677-96-8 1-(thiophen-2-ylmethylene)-2-phenylhydrazine 
• 27757-85-3 2-Aminomethylthiophene 
• 21124-40-3 D,L-(2-thienyl)glycine 
• 636-72-6 2-thiophenemethanol 

Relevant articles and documents

Eutectic salts promote green synthesis of bis(indolyl) methanes

A convenient and rapid method for the electrophilic substitution reaction of indoles with carbonyl compounds has been developed by using deep eutectic solvent as green and reusable catalysts to afford the corresponding bis(indolyl) methanes in excellent y

Cu-isatin schiff base complex supported on magnetic nanoparticles as an efficient and recyclable catalyst for the synthesis of bis(indolyl)methanes and bis(pyrazolyl)methanes in aqueous media

Cu-isatin Schiff base supported on γ-Fe2O3as a new catalyst was synthesized and characterized by different methods such as SEM, TEM, XRD, TGA, FT-IR, ICP, VSM and CHN analysis. It was used as a reusable heterogeneous catalyst for the

A versatile and practical synthesis of bis(indolyl)methanes/bis(indolyl) glycoconjugates catalyzed by trichloro-1,3,5-triazine

A practical and efficient electrophilic substitution reaction of indoles with aldehydes using catalytic trichloro-1,3,5-triazine (10 mol %) in acetonitrile to furnish the corresponding bis(indolyl)methanes in excellent yields is reported.

An easy and efficient synthesis of bisindolylmethanes and tetraindolylmethane Tr?ger's base catatlyzed by AgBF4

This work presents a highly efficient and simplemethod for the synthesis of bisindolylmethanes, catalyzed by AgBF4, with excellent yields. Various substituted aldehydes and ketones with indole under this reaction condition is elucidated. This r

Graphene oxide decorated with Cu(i)Br nanoparticles: A reusable catalyst for the synthesis of potent bis(indolyl)methane based anti HIV drugs

A GO-Cu(i)Br nanocatalyst has been prepared, and applied for the synthesis of bis(indolyl)methanes. The catalyst is highly effective, is required in much lower amounts (0.05 mol%), and is recyclable for up to six reaction cycles without loss in activity. The synthesized compounds have been screened for their in vitro anti-HIV-1 activity, and compound 3d has shown significant anti-HIV-1 effects. Molecular modelling of 3d with reverse transcriptase enzyme has been carried out to understand its binding mechanism to the active enzyme site.

Metal-free oxidative coupling of arylmethylamines with indoles: A simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes

The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3′-bis(indolyl)methanes in excellent yields of up to 95% via C-C and C-N bond formation. This attractive and environmentally friendly one-pot protocol is a simple procedure that features inexpensive acetic acid as the catalyst and molecular oxygen as the sole oxidant, and it supports a wide substrate scope with the good tolerance of functional groups.

P-sulfonic acid calix[4]arene: An efficient reusable organocatalyst for the synthesis of bis(indolyl)methanes derivatives in water and under solvent-free conditions

In this work, a green, simple and highly efficient procedure for the synthesis of bis(indolyl)methanes is described. The condensation of indoles catalyzed by p-sulfonic acid calix[4]arene in water and under solvent-free conditions afford the title compoun

One-pot conversion of aromatic compounds to the corresponding bis(indolyl)methanes by the Vilsmeier-Haack reaction

Various electron-rich aromatics could be smoothly converted into the corresponding bis(indolyl)methanes in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with indole at room temperature. The present article is the first report on a novel metal-free one-pot method for the preparation of bis(indolyl)methanes from electron-rich aromatics.

Synthesis and Catalytic Application of Bimetallic and Trimetallic Magnetic Nanoalloys for the Preparation of Bis(indolyl)methanes

Abstract: Some bimetallic and trimetallic magnetic nanoalloys based on cobalt, copper,and silver have been synthesized and used as and green catalysts for thepreparation of bis(indolyl)methanes through electrophilic substitution reactionof indole with car

Efficient FeIII-catalyzed synthesis of bis(indolyl)methanes in ionic liquids

An efficient synthesis of bis(indolyl)methanes through Fe III-catalyzed electrophilic substitution reactions of indoles with various aldehydes in ionic liquid is described. It was found that the ionic liquids involving FeCl3·6H2

The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale

Herein, a nano acid-base catalyst using magnetic core and carbamodithioic acid functional group have been synthesized and characterized. Its efficiency in the synthesis of dihydroquinazolinones and bis(indolyl)methanes derivatives was investigated. This novel metal-free catalyst exhibited significant catalytic activity in both reactions under green and mild reaction conditions (the yield obtained for the first reaction products: 82–98 % and for the second one: 61–97 %). The catalyst displayed good recyclability with no significant loss of catalytic activity after eight runs (the conversion of the eighth run was found as 83 %, the fresh catalyst conversion was 95 %). The introduced approach is attractive due to its applicability in the large-scale synthesis of important medicinal compounds.

Sulphamic acid - A mild, efficient, and cost-effective solid acid catalyst for the synthesis of bis(1H-indol-3-yl)methanes

Sulphamic acid (SA) is found to efficiently catalyze the electrophilic substitution reactions of indoles with aldehydes and ketones in ethanol to afford the corresponding bis(indolyl)methanes. The method is simple and cost effective, and gives good yields

Tetrabutylammonium tribromide as efficient catalyst in the synthesis of bis(indolyl)methanes

An efficient procedure has been developed for the synthesis of bis(indolyl)methane derivatives by condensation of aldehydes with indole in the presence of tetrabutylammonium tribromide as catalyst.

Rare earth perfluorooctanoate [RE(PFO)3]-catalyzed condensations of indole with carbonyl compounds

New rare earth perfluorooctanoates [RE(PFO)3] were developed and applied to the condensation reactions of indole with carbonyl compounds at ambient temperature. It was found that these catalysts could be completely recovered and reused without

An eco-friendly procedure for the efficient synthesis of bis(indolyl)methanes in aqueous media

A new, convenient and high yielding procedure for the preparation of bis(indolyl)methanes in water by electrophilic substitution reaction of indoles with different carbonyl compounds in the presence of a catalytic amount of [Cu(3,4-tmtppa)](MeSO4/su

Green protocol for synthesis of bis-indolylmethanes and bis-indolylglycoconjugates in the presence of iron(III) fluoride as a heterogeneous, reusable, and eco-friendly catalyst

An efficient method for the preparation of bis-indolylmethanes and bis-indolylglycoconjugates from carbonyl compounds with indoles in the presence of a catalytic amount of iron(iii) fluoride under solvent-free conditions is reported. The desired products

An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride

Zirconium tetrachloride is used as a catalyst for the electrophilic substitution reaction of indole with aldehydes or ketones at ambient temperature to afford the corresponding bis(indolyl)methanes in good to excellent yields. Georg Thieme Verlag Stuttgar

Evaluation of Nano-Fe3O4 as a green catalyst for the synthesis of mono, bis and tris diindolyl methanes

Fast and clean synthesis of mono, bis and tris diindolylmethanes from various aldehydes and indoles in the presence of an efficient reusable catalyst, nano-Fe3O4, in high yield and short reaction time is reported.

Ionic liquid 3-methyl-1-sulfonic acid imidazolium chloride as a novel and highly efficient catalyst for the very rapid synthesis of bis(indolyl)methanes under solvent-free conditions

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Photoacid-Catalyzed Friedel-Crafts Arylation of Carbonyls

In this report, we demonstrate that visible-light-induced thiourea photoacids catalyze C-C bond-forming reactions. Upon photoirradiation, Schreiner's thiourea [(N,N′-bis[3,5-bis(trifluoromethyl)phenyl]-thiourea] catalyzes the double Friedel-Crafts additio

Efficient and solvent-free synthesis of bis-indolylmethanes using silica gel supported aluminium chloride as a reusable catalyst

Stable and non-hygroscopic silica gel supported aluminium chloride (SiO2-AlCl3), which is prepared easily from cheap and commercially available compounds was found to be an environmentally friendly heterogeneous catalyst for the cond

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Fe+3-Montmorillonite K10, as effective, eco-friendly, and reusable catalyst for the synthesis of bis(1H-indol-3-yl)methanes under grinding condition

Bis(indoyl)methanes have been synthesized via electrophilic reaction of indole and aldehydes in excellent yields under mild reaction conditions in the presence of Fe+3-montmorillonite K10 as catalyst. The catalyst can be recovered and recycled in subsequent reactions without any apparent loss of activity.

Well-Defined NNS-Mn Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Using Alcohols

Herein, we demonstrated Mn-catalyzed selective C-3 functionalization of indoles with alcohols. The developed catalyst can also furnish bis(indolyl)methanes from the same set of substrates under slightly modified reaction conditions. Mechanistic studies reveal that the C-3 functionalization of indoles is going via a borrowing hydrogen pathway. To highlight the practical utility, a diverse range of substrates including nine structurally important drug molecules are synthesized. Furthermore, we also introduced a one-pot cascade strategy for synthesizing C-3 functionalized indoles directly from 2-aminophenyl ethanol and alcohol.

Application of Magnetically Recoverable Core–Shell Nanocomposite in the Synthesis of Bis(indolyl)methanes at Room Temperature

Abstract: A sulfonated polyethylene glycol-supported nano-magnetite (Fe3O4@PEG-SO3H) has been prepared, characterized, and evaluated as a magnetically recoverable core–shell nanocomposite catalyst for the synthesis of bis(