23833-99-0

Basic information

• Product Name: 4-CHLORO-8-NITROQUINOLINE
• Synonyms: 4-CHLORO-8-NITROQUINOLINE;Quinoline, 4-chloro-8-nitro-
• CAS NO: 23833-99-0
• Molecular Formula: C₉H₅ClN₂O₂
• Molecular Weight: 208.6012
• Mol File: 23833-99-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 127-128 °C
• Boiling Point: 339.9±27.0 °C(Predicted)
• Appearance: /
• Density: 1.484±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.22±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-8-NITROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-8-NITROQUINOLINE(23833-99-0)
• EPA Substance Registry System: 4-CHLORO-8-NITROQUINOLINE(23833-99-0)

Safety Data

• Hazardous Substances Data: 23833-99-0(Hazardous Substances Data)

Usage

General Description

4-CHLORO-8-NITROQUINOLINE is a chemical compound that consists of a quinoline core with a chloro and nitro substituent on the 4th and 8th positions, respectively. It is primarily used in the pharmaceutical industry as a building block for the synthesis of a variety of bioactive compounds and drug candidates. This chemical has also shown potential as an antimicrobial and antifungal agent, with studies demonstrating its efficacy against various pathogens. Additionally, 4-CHLORO-8-NITROQUINOLINE has been investigated for its potential use in the development of new materials and organic electronic devices due to its unique electronic and optical properties. Overall, this compound has diverse applications in the fields of medicine, materials science, and electronics research.

Upstream product

• 611-35-8 4-chloroquinoline 
• 25063-47-2 2,2-dimethyl-5-(((2-nitrophenyl)amino)methylene)-1,3-dioxane-4,6-dione 
• 88-74-4 2-nitro-aniline 
• 56-57-5 4-nitroquinoline-N-oxide 
• 611-36-9 quinolin-4-ol 
• 132664-49-4 8-acetyl-3-ethoxycarbonyl-1,4-dihydro-4-oxoquinoline 
• 83475-06-3 8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 551-93-9 2-aminoacetophenone 
• 529-37-3 4(1H)-quinolinone 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 194784-10-6 acetic acid-(2-acetyl-6-nitro-anilide) 
• 68-12-2 N,N-dimethyl-formamide 
• 23833-95-6 8-nitro-4(1H)-quinolinone 

Downstream Products

• 89770-28-5 4-methoxy-8-nitroquinoline 
• 363609-03-4 8-nitro-4-phenoxy-quinoline 
• 578-66-5 8-amino quinoline 
• 23432-46-4 8-nitro-quinolin-4-ol 
• 89770-26-3 8-nitro-[4]quinolylamine 
• 81764-16-1 4-chloro-8-aminoquinoline 
• 53867-98-4 4,8-Diaminochinolin 
• 49713-55-5 4-chloro-8-iodoquinoline 
• 59665-93-9 4-methoxyquinoline-8-amine 

Relevant articles and documents

Synthesis of quinolinylaminopyrimidines and quinazolinylmethylaminopyrimidines with antiproliferative activity against melanoma cell line

Synthesis of a new series of quinolinylaminopyrimidines 1a-k and quinazolinylmethylaminopyrimidines 2a-i containing aminoquinoline and aminoquinazoline as hinge regions is described. Their in vitro antiproliferative activities against A375P human melanoma cell line were tested. Among them, compounds 1h and 1k exhibited the highest antiproliferative activities against A375P cell line with IC50 values in sub-micromolar scale. Compounds 1i, 2b and 2g showed similar potency against A375P to Sorafenib as a reference compound. The representative compound 1h showed high, dose-dependent inhibition of MEK and ERK kinases.

Direct amination of nitroquinoline derivatives via nucleophilic displacement of aromatic hydrogen

The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.

Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant

A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.