163485-86-7

Basic information

• Product Name: 8-BROMO-2-CHLOROQUINOLINE
• Synonyms: 8-BROMO-2-CHLOROQUINOLINE
• CAS NO: 163485-86-7
• Molecular Formula: C₉H₅BrClN
• Molecular Weight: 242.4997
• Mol File: 163485-86-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 113-114 °C(Solv: methanol (67-56-1))
• Boiling Point: 325.741 °C at 760 mmHg
• Flash Point: 150.803 °C
• Appearance: /
• Density: 1.673
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.33±0.50(Predicted)
• CAS DataBase Reference: 8-BROMO-2-CHLOROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-BROMO-2-CHLOROQUINOLINE(163485-86-7)
• EPA Substance Registry System: 8-BROMO-2-CHLOROQUINOLINE(163485-86-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 163485-86-7(Hazardous Substances Data)

Usage

General Description

8-Bromo-2-chloroquinoline, also known under its CAS number 14526-81-3, is a chemical substance often used in scientific research, particularly in the formulation of various pharmaceutical agents. As its name suggests, it has bromine and chlorine components, which allows it to participate in several types of chemical reactions. While its specific properties, such as flammability and reactivity, may vary depending on its state and the conditions it is stored or used in, like many other quinoline derivatives, it is typically handled with care due to potential health hazards. As of now, there is no widely available information on its applications outside of laboratory settings, as its primary use is in research and development activities.

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

Upstream product

• 1613-37-2 Quinoline N-oxide 
• 90279-39-3 8-bromoquinoline N-oxide 
• 71910-51-5 N-(2-bromophenyl)-3-phenylacrylamide 
• 67805-67-8 2-hydroxy-8-bromoquinoline 
• 615-36-1 2-bromoaniline 
• 71910-51-5 E-N-(2-bromophenyl)-3-phenylpropenamide 
• 67805-67-8 8-bromo-1H-quinoline-2-one 

Downstream Products

• 590371-88-3 8-bromo-2-chloro-3-iodoquinoline 
• 146564-18-3 8-bromo-2-(methyloxy)quinoline 
• 1374876-29-5 2-(benzyloxy)-8-bromoquinoline 
• 1374876-30-8 tert-butyl 4-(2-(benzyloxy)quinolin-8-yl)piperazine-1-carboxylate 
• 1374876-32-0 8-(4-(Biphenyl-4-ylmethyl)piperazin-1-yl)-2-methoxyquinoline 
• 1374876-33-1 8-(4-((4'-fluorobiphenyl-4-yl)methyl)piperazin-1-yl)-2-methoxyquinoline 
• 1374876-34-2 2-methoxy-8-(4-((5-phenylpyridin-3-yl)methyl)piperazin-1-yl)quinoline 
• 1374876-35-3 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline 
• 1374876-36-4 8-(4-(3-cyclopentenylbenzyl)piperazin-1-yl)-2-methoxyquinoline 
• 1374876-38-6 8-(4-([1,1′-biphenyl]-4-ylmethyl)piperazin-1-yl)quinolin-2(1H)-one 
• 1374876-39-7 8-(4-((4'-fluorobiphenyl-4-yl)methyl)piperazin-1-yl)quinolin-2(1H)-one 
• 1374876-40-0 8-(4-((5-phenylpyridin-3-yl)methyl)piperazin-1-yl)quinolin-2(1H)-one 
• 1374876-41-1 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)quinolin-2(1H)-one 
• 1374876-42-2 8-(4-(3-cyclopentenylbenzyl)piperazin-1-yl)quinolin-2(1H)-one 

Relevant articles and documents

Computational and experimental evaluation of α-(N-2-quinolonyl)ketones: a new class of nonbiaryl atropisomers

Given the usefulness of atropisomers within both asymmetric catalysis and pharmaceuticals, a thorough computational study of substituted α-(N-2-quinolonyl)ketones has been conducted. This class of tertiary amides is unique, as the amide is embedded within an aromatic construct, and the nitrogen bears an aliphatic substituent. Using a computational approach, 8′-substituted quinolones were identified as potential class 2 and 3 atropisomeric targets with calculated C–N rotational barriers of greater than 20?kcal/mol. These results, along with experimental efforts toward the synthesis of these targets, are reported.

Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation

A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time.

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).