99455-15-9

Basic information

• Product Name: 7-BROMO-2-CHLORO-QUINOLINE
• Synonyms: 7-BROMO-2-CHLORO-QUINOLINE;Quinoline, 7-bromo-2-chloro-
• CAS NO: 99455-15-9
• Molecular Formula: C₉H₅BrClN
• Molecular Weight: 242.5
• Mol File: 99455-15-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 120-121 °C
• Boiling Point: 325.7 °C at 760 mmHg
• Flash Point: 150.8 °C
• Appearance: /
• Density: 1.673 g/cm³
• Vapor Pressure: 0.000429mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.25±0.50(Predicted)
• CAS DataBase Reference: 7-BROMO-2-CHLORO-QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMO-2-CHLORO-QUINOLINE(99455-15-9)
• EPA Substance Registry System: 7-BROMO-2-CHLORO-QUINOLINE(99455-15-9)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 99455-15-9(Hazardous Substances Data)

Usage

General Description

7-Bromo-2-chloro-quinoline is an organic compound that belongs to the class of quinoline derivatives. It is a light yellow solid with a molecular weight of 238.47 g/mol. This chemical is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also used in the manufacturing of dyes and pigments. 7-Bromo-2-chloro-quinoline is a versatile building block in organic synthesis and has numerous applications in the pharmaceutical and chemical industries due to its unique chemical properties. However, it is important to handle this compound with care as it can be harmful if ingested or inhaled and can cause irritation to the skin and eyes.

InChI:InChI=1/C9H5BrClN/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5H

Upstream product

• 591-19-5 m-Bromoaniline 
• 99465-18-6 (E)-N-(3-bromophenyl)-3-ethoxypropenamide 
• 99465-10-8 7-bromo-1,2-dihydroquinolin-2-one 
• 99465-10-8 7-bromo-quinolin-2-ol 
• 917341-34-5 (2E)-N-(3-bromophenyl)-3-phenylprop-2-enamide 
• 99465-09-5 5-bromoquinolin-2(1H)-one 
• 163485-85-6 7-Trimethylstannylquinoline 
• 349426-35-3 N-(3-bromophenyl)cinnamamide 

Downstream Products

• 445041-75-8 (R)-(+)-2-{4-[(7-bromo-2-quinolinyl)oxy]phenoxy}propionic acid 

Relevant articles and documents

From fragment screening to in vivo efficacy: Optimization of a series of 2-aminoquinolines as potent inhibitors of beta-site amyloid precursor protein cleaving enzyme 1 (bace1)

Using fragment-based screening of a focused fragment library, 2-aminoquinoline 1 was identified as an initial hit for BACE1. Further SAR development was supported by X-ray structures of BACE1 cocrystallized with various ligands and molecular modeling studies to expedite the discovery of potent compounds. These strategies enabled us to integrate the C-3 side chain on 2-aminoquinoline 1 extending deep into the P2′ binding pocket of BACE1 and enhancing the ligand's potency. We were able to improve the BACE1 potency to subnanomolar range, over 106-fold more potent than the initial hit (900 μM). Further elaboration of the physical properties of the lead compounds to those more consistent with good blood-brain barrier permeability led to inhibitors with greatly improved cellular activity and permeability. Compound 59 showed an IC50 value of 11 nM on BACE1 and cellular activity of 80 nM. This compound was advanced into rat pharmacokinetic and pharmacodynamic studies and demonstrated significant reduction of Aβ levels in cerebrospinal fluid (CSF).

Synthesis and in vitro antiproliferative activities of quinoline derivatives

The synthesis of new di- and trimeric quinoline derivatives is described as well as their in vitro antiproliferative activities toward a human fibroblast primary culture and two human solid cancer cell lines (MCF-7 and PA 1).

2-QUINOLINONE AND 2-QUINOXALINONE- DERIVATIVES AND THEIR USE AS ANTIBACTERIAL AGENTS

The present invention relates to compounds of Formula (I) : and pharmaceutically acceptable salts thereof, to their use in the treatment of bacterial infections, and to their methods of preparation.