1022094-18-3

Basic information

• Product Name: 4-chloro-8-tosyloxyquinoline
• Synonyms: 4-chloro-8-tosyloxyquinoline;4-Chloroquinolin-8-yl 4-Methylbenzenesulfonate
• CAS NO: 1022094-18-3
• Molecular Formula: C₁₆H₁₂ClNO₃S
• Molecular Weight: 333.78938
• Mol File: 1022094-18-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-chloro-8-tosyloxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-8-tosyloxyquinoline(1022094-18-3)
• EPA Substance Registry System: 4-chloro-8-tosyloxyquinoline(1022094-18-3)

Safety Data

• Hazardous Substances Data: 1022094-18-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-chloro-8-tosyloxyquinoline is used as a precursor in the synthesis of various pharmaceuticals. Its unique structure and functional groups contribute to the development of new drugs and bioactive molecules, enhancing the therapeutic potential of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-chloro-8-tosyloxyquinoline is utilized as a starting material for the creation of novel agrochemicals. Its chemical properties allow for the design of effective pesticides and other agricultural chemicals that can improve crop protection and yield.
Used in Organic Synthesis:
4-chloro-8-tosyloxyquinoline serves as an intermediate in organic synthesis, facilitating the production of a wide range of organic compounds. Its versatility makes it a key component in the synthesis of complex organic molecules for various applications.
Safety Note:
It is crucial to handle 4-chloro-8-tosyloxyquinoline with care due to its potential hazards to health and the environment. Proper management and safety measures should be strictly adhered to during its use in research and industrial applications.

Upstream product

• 59-00-7 xanthurenic acid 
• 14959-84-3 4,8-dihydroxyquinoline 

Downstream Products

• 1022094-23-0 4-pyrrolidinyl-8-hydroxyquinoline 
• 6435-78-5 N-tosylpyrrolidine 
• 1022094-19-4 4-(1H-pyrazol-1-yl)quinolin-8-yl 4-methylbenzenesulfonate 
• 57334-36-8 4-chloro-8-hydroxyquinoline 
• 1022094-20-7 C₂₀H₁₇N₃O₃S 
• 1108187-56-9 4-phenylquinolin-8-yl 4-methylbenzenesulfonate 
• 1108187-60-5 4-p-cyanophenyl-8-tosyloxyquinoline 
• 1108187-61-6 4-(pyridin-4-yl)-8-tosyloxyquinoline 
• 1108187-59-2 4-p-methoxyphenyl-8-tosyloxyquinoline 
• 1108187-57-0 4-p-methylphenyl-8-tosyloxyquinoline 
• 1108187-58-1 4-o-methylphenyl-8-tosyloxyquinoline 
• 1108187-62-7 4-o-(ethoxycarbonyl)phenyl-8-tosyloxyquinoline 

Relevant articles and documents

Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.

Synthesis of 8-hydroxyquinolines with amino and thioalkyl functionalities at position 4

(Chemical Equation Presented) Six 8-hydroxyquinolines with amino and thioalkyl functionalities at position 4 have been prepared. The synthesis starts with chlorination of the readily available 4-hydroxy-8-tosyloxyquinoline to give 4-chloro-8-tosyloxyquinoline in 94% yield. Treatment of the 4-chloro-8-tosyloxyquinoline with sulphur and nitrogen nucleophiles produces the target 4-amino and 4-thioalkyl-8-hydroxyquinolines in more than 70% yield. In case of sulphur nucleophiles and pyrrolidine, the removal of the protecting tosyl group at position 8 occurs simultaneously with the substitution of chlorine at position 4.