1599461-87-6

Basic information

• Product Name: 5-methoxy-3-(phenylselenyl)-1H-indole
• Synonyms: 5-methoxy-3-(phenylselenyl)-1H-indole
• CAS NO: 1599461-87-6
• Molecular Weight: 302.234
• Mol File: 1599461-87-6.mol

Chemical Properties

• CAS DataBase Reference: 5-methoxy-3-(phenylselenyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxy-3-(phenylselenyl)-1H-indole(1599461-87-6)
• EPA Substance Registry System: 5-methoxy-3-(phenylselenyl)-1H-indole(1599461-87-6)

Safety Data

• Hazardous Substances Data: 1599461-87-6(Hazardous Substances Data)

Upstream product

• 1006-94-6 5-methoxylindole 
• 645-96-5 Benzeneselenol 
• 1132-39-4 diphenylselenide 
• 591-50-4 iodobenzene 
• 1666-13-3 diphenyl diselenide 

Relevant articles and documents

Visible-light-induced metal and reagent-free oxidative coupling of: Sp 2 C-H bonds with organo-dichalcogenides: Synthesis of 3-organochalcogenyl indoles

Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C-H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone at room temperature. This benign protocol allows one to access a wide range of 3-arylselenylindoles, 3-arylthioindoles and even 3-aryltelluroindoles with good to excellent yields. Various functionalities namely, methoxy, and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C-H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene radical cation and a superoxide radical anion. Subsequently, reaction of the radical cation with aryl dichalcogenides provides a diaryl chalcogenyl cation which upon removal of protons gave unsymmetrical 3-indolyl aryl chalcogenides.

Atom-economical selenation of electron-rich arenes and phosphonates with molecular oxygen at room temperature

Organoselenium and selenophosphorus compounds are ubiquitously found in biologically active compounds, agrochemicals, functionalized materials etc. Although selenium is a micronutrient and an essential trace element, its contamination/consumption in highe

Convenient synthesis of selenyl-indoles via iodide ion-catalyzed electrochemical C-H selenation

Reported herein is a transition metal- and oxidant-free method for the synthesis of selenyl heteroarenes with diselenides through iodide ion-catalyzed electrolytic selenation. This direct C(sp2)-H selenation strategy, with reduced environmental

Preparation method of 3-arylseleno-1H-indoles

The invention provides a preparation method of 3-arylseleno-1H-indoles. Specifically, corresponding 3-arylseleno-1H-indoles are generated from aromatic heterocyclic compounds and symmetric diselenidesthrough a reaction in an organic solvent under irradiation of a blue LED lamp, preferably, the reaction is performed in presence of FIrPic (bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium). The preparation method is simple and convenient to operate, a reagent is obtained easily, a catalyst is safe and pollution-free, the requirement of green chemistry is met, and the catalyst is stable inproperty and high in catalytic efficiency; yield and purity of 3-arylseleno-1H-indoles prepared with the method are both higher.

Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3

Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp2)?H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes.

Rose Bengal catalysed photo-induced selenylation of indoles, imidazoles and arenes: A metal free approach

In this report, the highly efficient Rose Bengal-catalysed C(sp2)-H selenylation of indoles, imidazoles and arenes was achieved using a half molar equiv. of diorganoyl diselenides. This metal-free, photo-induced protocol resulted in selenylated

NaBr mediated regioselective synthesis of 3-Selanylindoles

A convenient NaBr mediated procedure is developed for the preparation of 3-selanylindoles from indoles and diselenides. In this protocol, NaBr is first oxidized by mCPBA into molecular bromine, which reacts with diselenide to form RSeBr. The in situ generated active electrophilic selenium species, then reacts with indoles, affording a series of 3-selanylindoles with high regioselectivity and in moderate to good yields.

Selective synthesis of 3-Selanylindoles from Indoles and Diselenides using IK/mCPBA system

In the presence of a catalytic amount of KI combined with oxidant mCPBA, a convenient catalytic procedure is developed for the preparation of 3-selanylindoles from indoles and diselenides. In this protocol, KI is first oxidized by mCPBA into hypoiodous acid, which reacts with diselenide to cleave Se-Se bond. The in situ generated active electrophilic selenium species then reacts with indole, affording 3-selanylindole via an electrophilic substitution mechanism. This catalytic selenation of indoles has mild reaction conditions and is a simple procedure, which extends the synthetic application of KI in organic synthesis.

Visible-light-mediated aerobic selenation of (hetero)arenes with diselenides

The first visible-light driven aerobic oxidation for the direct selenation of (hetero)arenes has been developed at room temperature, providing an eco-friendly, atom-economical protocol to prepare unsymmetrical selenides from easily accessible diselenides.

Copper-Catalyzed Three-Component Reaction for Regioselective Aryl- and Heteroarylselenation of Indoles using Selenium Powder

A new and efficient copper-catalyzed C3 aryl- and heteroarylselenation of indoles employing selenium powder has been developed. The advantages of this chemistry involve the use of cheap selenating reagents, tolerance of a variety of functional groups, and practicality. In addition, this protocol has been further elaborated in an intramolecular phenylselenation of a (hetero) aryl C-H bond to construct an important motif of benzoselenopheno[3,2-b]indole. A preliminary mechanism study suggests that the reaction starts with a Ullman-type selenation between aryl iodides and selenium, followed by an oxidative cross-coupling with indole. The utility of this method has been demonstrated in an efficient gram-scale synthesis and an application to the synthesis of tubulin polymerization inhibitor.