132664-45-0

Basic information

• Product Name: 4-CHLORO-8-CYANOQUINOLINE
• Synonyms: 4-CHLORO-8-CYANOQUINOLINE;4-Chloro-8-quinolinecarbonitrile;4-Chloroquinoline-8-carbonitrile
• CAS NO: 132664-45-0
• Molecular Formula: C₁₀H₅ClN₂
• Molecular Weight: 188.61
• Mol File: 132664-45-0.mol

Chemical Properties

• Melting Point: 210-211 °C(Solv: acetone (67-64-1))
• Boiling Point: 340.3±22.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.34±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-8-CYANOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-8-CYANOQUINOLINE(132664-45-0)
• EPA Substance Registry System: 4-CHLORO-8-CYANOQUINOLINE(132664-45-0)

Safety Data

• Hazardous Substances Data: 132664-45-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-CHLORO-8-CYANOQUINOLINE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of novel drug candidates with potential therapeutic effects.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-CHLORO-8-CYANOQUINOLINE is utilized as a building block for the creation of new agrochemicals, aiming to enhance crop protection and yield.
Used in Organic Compounds Synthesis:
4-CHLORO-8-CYANOQUINOLINE serves as a versatile component in the synthesis of a range of organic compounds, contributing to the advancement of organic chemistry.
Used in Fluorescent Materials:
Leveraging its fluorescent properties, 4-CHLORO-8-CYANOQUINOLINE is employed in the development of fluorescent materials for applications in chemistry and materials science, such as in sensors, imaging, and diagnostics.
Used in Disease Treatment Research:
4-CHLORO-8-CYANOQUINOLINE and its derivatives are studied for their potential use in the treatment of various diseases, highlighting their importance in medicinal chemistry and drug discovery.

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 127285-75-0 8-cyano-3-ethoxycarbonyl-1,4-dihydro-4-oxoquinolone 
• 132664-44-9 8-cyano-1,4-dihydro-4-oxoquinolone-3-carboxylic acid 
• 1020252-22-5 2-{[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}benzonitrile 
• 848128-91-6 4-hydroxy-8-cyanoquinoline 
• 127285-55-6 8-cyano-1,4-dihydro-4-oxoquinolone 

Downstream Products

• 1357072-97-9 3-(8-cyanoquinolin-4-ylamino)-4-(4-fluorophenyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1357072-98-0 tert-butyl 3-{[8-(aminocarbonyl)quinolin-4-yl]amino}-4-(4-fluorophenyl)pyrrolidine-1-carboxylate 
• 1357071-02-3 4-((4-(4-fluorophenyl)pyrrolidin-3-yl)amino)quinoline-8-carboxamide 
• 132664-48-3 methyl 4-bromo-quinoline-8-carboxylate 

Relevant articles and documents

Palladium-Catalyzed C-O Cross-Coupling as a Replacement for a Mitsunobu Reaction in the Development of an Androgen Receptor Antagonist

A scalable and efficient synthesis of N-{trans-4-[(8-cyanoquinolin-4-yl)oxy]cyclohexyl}-3-fluorobenzamide (BAY 1161116), an androgen receptor antagonist, is reported. The original synthesis included a low-yielding Mitsunobu reaction and employed cis-aminocyclohexanol, which is accessible only via a troublesome synthesis, as a key building block. The novel synthetic pathway starts from readily available trans-aminocyclohexanol and features a palladium-catalyzed etherification reaction in place of the Mitsunobu reaction as the key step. This four-step synthesis can be performed reliably on a multikilogram scale, and purification of all intermediates as well as the final product can be achieved by simple extraction and crystallization procedures.

BICYCLIC ARYL AND HETEROARYL COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS

Compounds of formula (I): or pharmaceutically acceptable salts thereof, are opioid receptor modulators, e.g. mu- opioid receptor antagonists, neutral antagonists or inverse agonists, and are useful for the treatment of metabolic disorders including obesity.

Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2.