83515-06-4

Usage

Uses

Used in Pharmaceutical Research and Development:
1H-INDOLE, 5-BROMO-2-PHENYLis used as a building block for the synthesis of various bioactive molecules, contributing to the development of pharmaceutical drugs. Its unique structure and potential biological activities make it a valuable component in creating new therapeutic agents.
Used in Agrochemical Development:
1H-INDOLE, 5-BROMO-2-PHENYLis also studied for its potential application in the development of agrochemicals. Its properties may be harnessed to create new compounds with pesticidal or herbicidal activities, contributing to advancements in agricultural chemistry.
Used as a Dye Intermediate:
In the dye industry, 1H-INDOLE, 5-BROMO-2-PHENYLhas been investigated for its potential use as a dye intermediate. Its chemical structure may be utilized to synthesize new dyes with specific color properties, expanding the range of dyes available for various applications.
Used in Organic Synthesis:
1H-INDOLE, 5-BROMO-2-PHENYLis employed in organic synthesis for the preparation of various organic compounds. Its unique structure allows for the formation of new chemical entities, contributing to the advancement of organic chemistry and the development of novel compounds with diverse applications.

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 66416-72-6 4-bromo-2-iodoaniline 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 100-42-5 styrene 
• 613-94-5 benzoic acid hydrazide 
• 1538583-21-9 4-bromo-2-((trimethylsilyl)ethynyl)aniline 
• 1260776-51-9 4-bromo-2-ethynylbenzenamine 
• 98-86-2 acetophenone 
• 7702-38-7 N-(4-bromophenyl)benzamide 
• 51300-42-6 N-(4-bromophenyl)benzimidoyl chloride 
• 98-88-4 benzoyl chloride 
• 106-40-1 4-bromo-aniline 
• 116632-39-4 2-methyl-4-bromoiodobenzene 

Downstream Products

• 83515-10-0 5-bromo-2-phenyl-3H-indol-3-one 
• 1364952-72-6 N-(2-bromo-1-(5-bromo-2-phenyl-1H-indol-1-yl)-2,2-difluoroethylidene)-4-methoxyaniline 
• 1364953-45-6 N-(10-bromo-5,5-difluoroindolo[2,1-a]isoquinolin-6(5H)-ylidene)-4-methoxyaniline 
• 1402597-47-0 2,13-dibromo-15a-phenyl-5H-diindolo[1,2-a:3',2'-c]quinolin-15(15aH)-one 
• 1403946-48-4 C₂₈H₂₈F₃N₃O 
• 1403947-66-9 C₂₁H₂₃BrN₂O 
• 66387-70-0 6-bromo-2-phenyl-4H-benzo[2,3-d]-1,3-oxazin-4-one 
• 27398-50-1 6-bromo-2-phenyl-3H,4H-quinazolin-4-one 
• 700836-72-2 1-benzenesulfonyl-5-bromo-2-phenyl-1H-indole 
• 1263300-02-2 1-Benzenesulfonyl-2-phenyl-5-triisopropylsilanyloxymethylindole 
• 1263300-01-1 1-benzenesulfonyl-5-hydroxymethyl-2-phenylindole 
• 1263300-00-0 1-benzenesulfonyl-5-formyl-2-phenylindole 
• 1363261-49-7 (S)-N(α)-acetyl-5-bromo-2-phenyltryptophan methyl ester 

Relevant academic research and scientific papers

Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis

Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.

An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives

We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics

Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.

Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones

A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.

Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones

A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.

A Three-Component Strategy for Benzoselenophene Synthesis under Metal-Free Conditions Using Selenium Powder

An efficient three-component benzoselenophenes formation has been developed from substituted indoles, acetophenones, and selenium powder under metal-free conditions. 2-Aryl indoles played an important role to promote benzoselenophene formation from acetophenone derivatives and selenium powder. One C-C and two C-Se bonds were selectively formed to provide 40 new benzoselenophenes in good yields.