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
• Article Data: 4

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

General Description

4-CHLORO-8-CYANOQUINOLINE is a chemical compound with the molecular formula C11H6ClN3. It is a quinoline derivative, featuring a chlorine atom at the 4-position and a cyano group at the 8-position. This chemical is often used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It possesses a wide range of biological activities, and its derivatives have been studied for their potential use in the treatment of various diseases. 4-CHLORO-8-CYANOQUINOLINE is also known for its fluorescent properties, making it useful in a variety of applications in the field of chemistry and materials science.

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.

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.