93716-78-0

Basic information

• Product Name: 1H-INDOLE, 2-(3-BROMOPHENYL)-
• Synonyms: 1H-INDOLE, 2-(3-BROMOPHENYL)-;2-(3-BROMOPHENYL)-1H-INDOLE
• CAS NO: 93716-78-0
• Molecular Formula: C₁₄H₁₀BrN
• Molecular Weight: 272.144
• Mol File: 93716-78-0.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-INDOLE, 2-(3-BROMOPHENYL)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE, 2-(3-BROMOPHENYL)-(93716-78-0)
• EPA Substance Registry System: 1H-INDOLE, 2-(3-BROMOPHENYL)-(93716-78-0)

Safety Data

• Hazardous Substances Data: 93716-78-0(Hazardous Substances Data)

Usage

Description

1H-Indole, 2-(3-bromophenyl)-, also known as 2-(3-Bromophenyl)-1H-indole, is a chemical compound with the molecular formula C14H10BrN. It is a derivative of indole, a heterocyclic aromatic compound found in some plants. The presence of a bromophenyl group in this compound enables various chemical reactions and potential applications in organic synthesis. It has been studied for its potential biological activities, such as antiparasitic and anticancer properties, and has been investigated for its use in material science, particularly in the development of organic semiconductors for electronic devices. 1H-Indole, 2-(3-bromophenyl)is a versatile chemical with potential applications in various fields of science and industry.

Uses

Used in Organic Synthesis:
1H-Indole, 2-(3-bromophenyl)is used as a building block in organic synthesis for the development of new compounds with potential applications in pharmaceuticals, agrochemicals, and other industries. The presence of the bromophenyl group allows for various chemical reactions, making it a valuable intermediate in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
1H-Indole, 2-(3-bromophenyl)is used as a potential antiparasitic and anticancer agent in the pharmaceutical industry. Its biological activities have been studied, and it has shown promise in inhibiting the growth of certain parasites and cancer cells. Further research and development are needed to fully understand its therapeutic potential and optimize its use in drug discovery.
Used in Material Science:
1H-Indole, 2-(3-bromophenyl)is used in material science for the development of organic semiconductors for electronic devices. Its unique electronic properties and structural features make it a promising candidate for use in organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and other electronic applications. Ongoing research aims to improve the performance and stability of these materials for practical use in various electronic devices.

Upstream product

• 615-43-0 2-iodophenylamine 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 120-72-9 indole 
• 591-18-4 1-Bromo-3-iodobenzene 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 29835-28-7 3-(3-bromophenyl)propiolic acid 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 62-53-3 aniline 
• 52670-38-9 2-ethynylaniline 
• 1438414-72-2 2-[(3-bromophenyl)ethynyl]aniline 
• 66532-87-4 1-[1-(3-bromophenyl)ethylidene]-2-phenylhydrazine 

Downstream Products

• 914389-67-6 2-(3-iodophenyl)-1H-indole 
• 1438414-83-5 2-(3-bromophenyl)-3-fluoro-1H-indole 
• 1438414-78-8 2-(3-bromophenyl)-3,3-difluoro-3H-indole 
• 1309945-72-9 C₁₆H₁₂BrNO 
• 1309945-80-9 C₃₀H₂₀Br₂N₂ 

Relevant articles and documents

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.

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.

Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors

The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.