106050-92-4

Basic information

• Product Name: (2-bromo-1H-indol-3-yl)-acetonitrile
• Synonyms: (2-bromo-1H-indol-3-yl)-acetonitrile
• CAS NO: 106050-92-4
• Molecular Formula: C₁₀H₇BrN₂
• Molecular Weight: 235
• Mol File: 106050-92-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2-bromo-1H-indol-3-yl)-acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2-bromo-1H-indol-3-yl)-acetonitrile(106050-92-4)
• EPA Substance Registry System: (2-bromo-1H-indol-3-yl)-acetonitrile(106050-92-4)

Safety Data

• Hazardous Substances Data: 106050-92-4(Hazardous Substances Data)

Usage

General Description

(2-bromo-1H-indol-3-yl)-acetonitrile is a chemical compound with the molecular formula C10H8BrN. It is a derivative of indole, an aromatic heterocyclic organic compound. The compound contains a bromine atom and a nitrile group, which makes it a versatile building block for the synthesis of various organic molecules. It can be used in the pharmaceutical and agrochemical industries as a precursor for the preparation of complex bioactive compounds. Additionally, it has potential applications in materials science, such as in the development of organic semiconductors and dyes. The chemical properties of (2-bromo-1H-indol-3-yl)-acetonitrile make it a valuable tool for organic synthesis and research.

Upstream product

• 771-51-7 indole-3-acetonitrile 

Downstream Products

• 142273-18-5 paullone 
• 27005-52-3 2-(2-phenyl-1H-indol-3-yl)acetonitrile 
• 1312891-44-3 (E)-N-hydroxy-3-[4-({2-[2-(4-methoxypyrinin-3-yl)-1H-indol-3-yl]ethylamino}methyl)phenyl]acrylamide 
• 1312891-83-0 (E)-3-[4-({2-[2-(3,5-dimethylisoxazol-4-yl)-1H-indol-3-yl]ethylamino}methyl)phenyl]acrylic acid methyl ester 
• 1312891-82-9 (E)-3-[4-({2-[2-(4-methoxypyrinin-3-yl)-1H-indol-3-yl]ethylamino}methyl)phenyl]acrylic acid methyl ester 
• 901181-17-7 2-(2-(2-methoxyphenyl)-1H-indol-3-yl)acetic acid 
• 901181-38-2 2-(2-(o-tolyl)-1H-indol-3-yl)acetic acid 
• 901210-67-1 [2-(4-bromo-phenyl)-1H-indol-3-yl]-acetic acid 
• 901210-89-7 [2-(3-chloro-phenyl)-1H-indol-3-yl]-acetic acid 

Relevant articles and documents

A SUPERIOR SYNTHETIC METHOD FOR THE BROMINATION OF INDOLES AND BENZIMIDAZOLES.

Brominated indoles and benzimidazoles are formed in very high yields and with substantial regioselectivity by use of a reagent system consisting of N-bromosuccinimide (NBS) and silica gel in dichloromethane.

Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors

Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree of pharmacophore homology between these two targets was discovered. This similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homology model, two compounds, 11r and 25i, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.