147497-32-3

Basic information

• Product Name: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• Synonyms: 6-bromo-3,4-dihydroisoquinolin-1(2H)-one;6-BROMO-3,4-1(1H)-ISOQUINOLINONE;6-BROMO-3,4-DIHYDRO-1(1H)-ISOQUINOLINONE;6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ON;1(2H)-Isoquinolinone, 6-bromo-3,4-dihydro-;6-Bromo-3,4-dihydro-1(2H)-isoquinolinone;6-BroMo-1-oxo-1,2,3,4-tetrahydroisoquinoline;6-broMo-1,2,3,4-tetrahydroisoquinolin-1-one
• CAS NO: 147497-32-3
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.07
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 147497-32-3.mol
• Article Data: 36

Chemical Properties

• Melting Point: 170.0-173.1 °C
• Boiling Point: 453.294 °C at 760 mmHg
• Flash Point: 227.944 °C
• Appearance: /
• Density: 1.559 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.22±0.20(Predicted)
• CAS DataBase Reference: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(147497-32-3)
• EPA Substance Registry System: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(147497-32-3)

Safety Data

• Hazardous Substances Data: 147497-32-3(Hazardous Substances Data)

Usage

Description

6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which includes a bromo group at the 6th position, a 3,4-dihydroisoquinolinone core, and a 2H-isoquinolinone ring. 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE plays a significant role in the development of novel therapeutic agents targeting specific biological receptors.

Uses

Used in Pharmaceutical Industry:
6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is used as an intermediate in the synthesis of benzolactams, which are known as dopamine D3 receptor ligands. These ligands are essential for developing drugs that can modulate the activity of the dopamine D3 receptor, potentially leading to treatments for various neurological and psychiatric disorders.
6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is also used as an intermediate in the synthesis of new, selective 3-aminopyrazole-based MK2 inhibitors. These inhibitors have been proven to inhibit intracellular phosphorylation of hsp27 as well as LPS-induced TNFα release in cells. MK2 inhibitors hold promise in the development of therapeutic agents for inflammatory diseases and other conditions where the MK2 pathway is implicated.

InChI:InChI=1/C9H8BrNO/c10-7-1-2-8-6(5-7)3-4-11-9(8)12/h1-2,5H,3-4H2,(H,11,12)

Upstream product

• 34598-49-7 5-Bromo-1-indanone 
• 7732-18-5 water 
• 75-75-2 methanesulfonic acid 
• 1279816-33-9 methyl 3-bromophenethylcarbamate 
• 305447-65-8 methyl 4-(bromophen)ethylcarbamate 
• 58971-11-2 2-(3-bromophenyl)ethanamine 

Downstream Products

• 959755-58-9 (4-morpholin-4-yl-phenyl)-[5-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-carbamic acid tert-butyl ester 
• 735351-82-3 2-benzyl-6-bromo-3,4-dihydroisoquinolin-1(2H)-one 
• 879887-26-0 6-formyl-1-oxo-1,2,3,4-tetrahydroisoquinoline 
• 226942-29-6 6-bromo-1,2,3,4-tetrahydroisoquinoline 
• 877868-87-6 6-iodo-3,4-dihydroisoquinolin-1(2H)-one 
• 1131223-07-8 6-bromo-3,4-dihydro-2-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)iso-quinolin-1-one 
• 376584-30-4 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-1(2H)-one 
• 1178884-85-9 6-bromo-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one 
• 879887-28-2 6-bromo-2-ethyl-3,4-dihydroisoquinolin-1(2H)-one 
• 1251402-11-5 6-bromo-2-phenethyl-3,4-dihydroisoquinolin-1-one 
• 1092550-63-4 C₁₈H₁₄FNO 
• 1092550-59-8 C₁₇H₁₂FNO 
• 1092550-65-6 C₁₇H₁₂ClNO 
• 1309955-20-1 3,4-dihydro-6-ethynylisoquinolin-1(2H)-one 

Relevant articles and documents

New Series of Potent Allosteric Inhibitors of Deoxyhypusine Synthase

Deoxyhypusine synthase (DHPS) is the primary enzyme responsible for the hypusine modification and, thereby, activation of the eukaryotic translation initiation factor 5A (eIF5A), which is key in regulating the protein translation processes associated with tumor proliferation. Although DHPS inhibitors could be a promising therapeutic option for treating cancer, only a few studies reported druglike compounds with this inhibition property. Thus, in this work, we designed and synthesized a new chemical series possessing fused ring scaffolds designed from high-throughput screening hit compounds, discovering a 5,6-dihydrothieno[2,3-c]pyridine derivative (26d) with potent inhibitory activity; furthermore, the X-ray crystallographic analysis of the DHPS complex with 26d demonstrated a distinct allosteric binding mode compared to a previously reported inhibitor. These findings could be significantly useful in the functional analysis of conformational changes in DHPS as well as the structure-based design of allosteric inhibitors.

Rational Design of Cell-Active Inhibitors of PARP10

Poly-ADP-ribose polymerases (PARPs 1-16) have emerged as major regulators of diverse cellular processes. PARPs can be subclassified based on their ability to catalyze poly-ADP-ribosylation (PARylation) or mono-ADP-ribosylation (MARylation). While much is

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.