137433-23-9

Basic information

• Product Name: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
• CAS NO: 137433-23-9
• Molecular Formula: C₁₈H₂₆ClN₃O
• Molecular Weight: 335.8715
• Mol File: 137433-23-9.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 516.7°C at 760 mmHg
• Flash Point: 266.3°C
• Density: 1.176g/cm³
• Vapor Pressure: 1.68E-11mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol(137433-23-9)
• EPA Substance Registry System: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol(137433-23-9)

Safety Data

• Hazardous Substances Data: 137433-23-9(Hazardous Substances Data)

Usage

General Description

2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol, also known as Tafenoquine, is a medication used for the prevention of malaria. It belongs to the class of 8-Aminoquinoline antimalarial drugs and works by effectively killing the malaria parasites in the liver and preventing the development of the disease. Tafenoquine is thought to interfere with the parasite's ability to break down hemoglobin, leading to the build-up of toxic heme molecules that ultimately kill the parasites. It has a long half-life and can provide protection against malaria for up to several months after a single dose, making it particularly useful for travelers to malaria-endemic areas. However, it comes with potential side effects such as nausea, vomiting, and headache.

Upstream product

• 86-98-6 4,7-dichloroquinoline 
• 747-36-4 Plaquenil 
• 69559-11-1 rac-5--2-pentanamine 
• 74509-79-8 5-(N-ethyl-N-2-hydroxyethylamine)-2-pentanone 
• 3695-29-2 5-iodo-2-pentanone 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 103526-68-7 7-chloro-4-fluoroquinoline 
• 613-18-3 2,3-dichloroquinoline 
• 747-36-4 (±)-hydroxychloroquine sulfate 
• 159346-86-8 R(-)-5--2-pentanamine 
• 118-42-3 hydroxychloroquine 
• 1198-40-9 4-amino-7-chloroquinoline 
• 155204-10-7 S(+)-5--2-pentanamine 

Downstream Products

• 137433-23-9 (R)-Hydroxychloroquine 
• 137433-23-9 (S)-Hydroxychloroquine 
• 158749-75-8 C₁₈H₂₆ClN₃O*(x)H₃O₄P 
• 158749-75-8 C₁₈H₂₆ClN₃O*(x)H₃O₄P 
• 747-36-4 Plaquenil 
• 747-36-4 (S)-hydroxychloroquine sulfate 
• 747-36-4 R-(-)-hydroxychloroquine sulfate 
• 747-36-4 C₁₈H₂₆ClN₃O*(x)H₂O₄S 

Relevant articles and documents

A Practical Synthesis of the Enantiomers of Hydroxychloroquine

An efficient synthesis of the enantiomeric forms of hydroxychloroquine is described.The method is suitable for the production of multigram quantities of the dihydrogenphosphate salts (R)-1b and (S)-1b.

An asymmetric synthesis method of optically pure (R)/(S)-hydroxychloroquine side chains

The present invention provides an optically pure (R)/ (S) - hydroxychloroquine synthesis method, using a splitting reagent to (±) -2- [(4-aminopentyl)ethylamine] ethanol is split, and recrystallization purification, purified to give optically pure (R) / (S)-2- [(4-aminopentyl) ethylamine] ethanol, the resulting single configuration of hydroxychloroquine side chain and 4,7-dichloroquinoline reaction directly to obtain a single configuration of hydroxychloroquine sulfate. The method has a simple route, easy to obtain raw materials, high yield, good three-dimensional selectivity (ee% >99%), simple operation and green environmental protection, suitable for large-scale scale production.

Optically active chloroquine and hydroxychloroquine and analogues thereof, and preparation method, composition and application of optically active chloroquine and hydroxychloroquine

The invention provides a rapid and simple method for preparing optically active chloroquine, hydroxychloroquine and analogues thereof, which comprises the following steps: reacting racemates of chloroquine, hydroxychloroquine and analogues thereof with an acidic chiral resolution reagent to generate corresponding salts, and separating and purifying to obtain optically pure salts of chloroquine, hydroxychloroquine and analogues thereof, and reacting with alkali to obtain (R)- or (S)- chloroquine with high optical purity and (R)- or (S)- hydroxychloroquine and analogues thereof. The method is simple and convenient to operate and low in cost, the enantiomer purity can reach 99.9% ee, and industrial production of chloroquine, hydroxychloroquine and analogues thereof with single chiral configuration is easy to realize. The invention also provides (R)- or (S)- chloroquine and (R)- or (S)- hydroxychloroquine and analogues thereof, pharmaceutical compositions and uses thereof, optically activechloroquine and hydroxychloroquine and analogues thereof reduce toxic and side effects, and have better treatment effects on coronavirus, influenza virus and autoimmune diseases.