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

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

Uses

Used in Pharmaceutical Research and Development:
8-Bromo-2-chloroquinoline is used as a chemical intermediate for the synthesis of various pharmaceutical agents. Its unique structure, which includes bromine and chlorine components, allows it to participate in multiple chemical reactions, making it a valuable component in the creation of new drug molecules.
Used in Scientific Research:
8-Bromo-2-chloroquinoline is employed as a research compound in various scientific studies. Its reactivity and the ability to form different chemical bonds make it an important tool for understanding complex chemical processes and reactions.
Used in Chemical Synthesis:
8-Bromo-2-chloroquinoline is used as a reagent in chemical synthesis processes. Its bromine and chlorine atoms facilitate the formation of new compounds, which can be further utilized in various applications, including the production of pharmaceuticals and other chemical products.
Used in Laboratory Settings:
8-Bromo-2-chloroquinoline is primarily used in laboratory settings for research and development activities. Its potential health hazards necessitate careful handling and storage, making it essential for researchers to follow proper safety protocols when working with this chemical substance.

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

Upstream product

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

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.

BICYCLIC COMPOUNDS

Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.

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.

Synthesis of new 1-Aryl-4-(biarylmethylene)piperazine ligands, structurally related to adoprazine (SLV313)

A series of new 1-aryl-4-(biarylmethylene)piperazines has been synthesized. These ligands are structurally related to SLV-313, a potential atypical antipsychotic having potent D2 receptor antagonist and 5-HT 1A receptor agonist prope

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).

Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids

As part of a case study, rational strategies for the preparation of all ten 2-, 3-, or 4-pyridinecarboxylic acids and all nine 2-, 3-, 4-, or 8-quinolinecarboxylic acids bearing trifluoromethyl substituents at the 2-, 3-, or 4-position were elaborated. The trifluoromethyl group, if not already present in the precursor, was introduced either by the deoxygenative fluorination of suitable carboxylic acids with sulfur tetrafluoride or by the displacement of ring-bound bromine or iodine by trifluoromethylcopper generated in situ. The carboxy function was produced by treatment of organolithium or organomagnesium intermediates, products of halogen/metal or hydrogen/ metal permutation, with carbon dioxide. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Substituted piperazine derivatives, the preparation thereofand their use as medicaments

The present invention relates to substituted piperazine derivatives of general formula , (I wherein Ra, Rb, Rc, Rf, Rg, X, m and n are defined as in claim 1, the isomers and salts thereof, particularly the physiologically acceptable salts thereof, which are valuable inhibitors of the microsomal triglyceride-transfer protein (MTP), medicaments containing these compounds and their use, as well as the preparation thereof.