654655-68-2

Basic information

• Product Name: 3-benzyl-6-bromo-2-chloroquinoline
• Synonyms: 3-benzyl-6-bromo-2-chloroquinoline;6-Bromo-2-chloro-3-(phenylmethyl)quinoline;Bedaquiline Impurity B
• CAS NO: 654655-68-2
• Molecular Formula: C₁₆H₁₁BrClN
• Molecular Weight: 333
• Product Categories: bedaquiline intermediates
• Mol File: 654655-68-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 111-112℃
• Boiling Point: 435.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.482±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.42±0.50(Predicted)
• CAS DataBase Reference: 3-benzyl-6-bromo-2-chloroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-6-bromo-2-chloroquinoline(654655-68-2)
• EPA Substance Registry System: 3-benzyl-6-bromo-2-chloroquinoline(654655-68-2)

Safety Data

• Hazardous Substances Data: 654655-68-2(Hazardous Substances Data)

Usage

Uses

3-Benzyl-6-bromo-2-chloroquinoline is an intermediate in the synthesis of (αS,βR)-Bedaquiline (B119540), which is a diarylquinoline derivative that acts as a mycobacterial inhibitor. Bedaquiline shows promise as potential drug in the treatment of tuberculosis.

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 106-40-1 4-bromo-aniline 
• 68-12-2 N,N-dimethyl-formamide 
• 316146-27-7 N-(4-bromophenyl)-3-phenylpropanamide 
• 924658-20-8 2-[(4-bromo-phenylamino)-phenyl-methyl]-acrylic acid ethyl ester 
• 924633-09-0 3-benzyl-6-bromo-1H-quinolin-2-one 
• 105479-98-9 ethyl 2-(acetoxy(phenyl)methyl)acrylate 
• 37442-45-8 ethyl 2-(hydroxy(phenyl)methyl)propenoate 
• 75-05-8 acetonitrile 

Downstream Products

• 654655-70-6 intermediate compound 4 
• 924633-12-5 C₂₂H₁₆BrNO 
• 1228594-68-0 (1S,2R)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-(6-bromo-2-chloro-quinolin-3-yl)-butan-2-ol 
• 1228594-69-1 (1R,2S)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-(6-bromo-2-chloro-quinolin-3-yl)-butan-2-ol 
• 654653-93-7 (6-bromo-2-memoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 
• 654653-93-7 rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol 
• 843663-66-1 bedaquiline 
• 654655-80-8 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 
• 924632-90-6 (±)-3-bromo-3-(bromo(phenyl)methyl)-2-methoxyquinoline 
• 1032468-71-5 C₃₆H₃₇BrN₄O 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF BEDAQUILINE FUMARATE

The present disclosure relates to an improved process for the preparation of bedaquiline fumarate, comprising a step of preparing bedaquiline by reaction of 3-benzyl-6-bromo-2-methoxyquinoline 5 with 3-(dimethylamino)-l-(naphthalen-l-yl)propan-l-one 4 in the presence of lithium pyrrolidide.

Structural Simplification of Bedaquiline: the Discovery of 3-(4-(N,N-Dimethylaminomethyl)phenyl)quinoline-Derived Antitubercular Lead Compounds

Bedaquiline (BDQ) is a novel and highly potent last-line antituberculosis drug that was approved by the US FDA in 2013. Owing to its stereo-structural complexity, chemical synthesis and compound optimization are rather difficult and expensive. This study

NEW QUINOLINE DERIVATIVES, A METHOD FOR THE PRODUCTION AND THE USE THEREOF FOR TREATING MICROBACTERIAL INFECTIONS AND A PHARMACEUTICAL COMPOSITION BASED ON SAID DERIVATIVES

The invention relates to the new derivatives of the quinoline, their stereoisomers or mixtures in any proportion, pharmaceutically acceptable acidic or basic additive salts, including solvates that have the mycobacterial activity, to the process of their