4225-86-9

Basic information

• Product Name: 2-Chloro-8-nitroquinoline
• Synonyms: 2-Chloro-8-nitroquinoline;Quinoline, 2-chloro-8-nitro-;NSC 263744;MFCD00160589
• CAS NO: 4225-86-9
• Molecular Formula: C₉H₅ClN₂O₂
• Molecular Weight: 208.6012
• Mol File: 4225-86-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 149℃ (ethanol )
• Boiling Point: 351.7 °C at 760 mmHg
• Flash Point: 166.5 °C
• Appearance: /
• Density: 1.484 g/cm³
• Vapor Pressure: 8.18E-05mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-Chloro-8-nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-8-nitroquinoline(4225-86-9)
• EPA Substance Registry System: 2-Chloro-8-nitroquinoline(4225-86-9)

Safety Data

• Hazardous Substances Data: 4225-86-9(Hazardous Substances Data)

Usage

General Description

2-Chloro-8-nitroquinoline is a chemical compound with the molecular formula C9H6ClNO2. It is a yellow solid that is used as an intermediate in the synthesis of pharmaceutical and agricultural chemicals. 2-Chloro-8-nitroquinoline is known for its antimicrobial and antifungal properties and is used in the production of drugs and pesticides. 2-Chloro-8-nitroquinoline is also a potential mutagenic compound and is therefore considered hazardous. It should be handled with proper safety precautions and disposed of according to local regulations to minimize its impact on human health and the environment.

InChI:InChI=1/C9H5ClN2O2/c10-8-5-4-6-2-1-3-7(12(13)14)9(6)11-8/h1-5H

Upstream product

• 612-62-4 2-Chloroquinoline 
• 14753-18-5 8-nitro-quinoline N-oxide 

Downstream Products

• 874498-16-5 (4-chloro-phenyl)-(8-nitro-[2]quinolyl)-amine 
• 7461-11-2 2-chloro-8-aminoquinoline 
• 7461-12-3 8-nitroquinolin-2-ol 
• 7461-12-3 8-Nitroquinolin-2(1H)-one 
• 53868-02-3 8-amino-2(1H)-quinolinone 
• 25771-64-6 8-nitro-2-phenylquinoline 

Relevant articles and documents

Antitrypanosomatid Pharmacomodulation at Position 3 of the 8-Nitroquinolin-2(1H)-one Scaffold Using Palladium-Catalysed Cross-Coupling Reactions

An antikinetoplastid pharmacomodulation study at position 3 of the recently described hit molecule 3-bromo-8-nitroquinolin-2(1H)-one was conducted. Twenty-four derivatives were synthesised using the Suzuki–Miyaura cross-coupling reaction and evaluated in vitro on both Leishmania infantum axenic amastigotes and Trypanosoma brucei brucei trypomastigotes. Introduction of a para-carboxyphenyl group at position 3 of the scaffold led to the selective antitrypanosomal hit molecule 3-(4-carboxyphenyl)-8-nitroquinolin-2(1H)-one (21) with a lower reduction potential (?0.56 V) than the initial hit (?0.45 V). Compound 21 displays micromolar antitrypanosomal activity (IC50=1.5 μm) and low cytotoxicity on the human HepG2 cell line (CC50=120 μm), having a higher selectivity index (SI=80) than the reference drug eflornithine. Contrary to results previously obtained in this series, hit compound 21 is inactive toward L. infantum and is not efficiently bioactivated by T. brucei brucei type I nitroreductase, which suggests the existence of an alternative mechanism of action.

Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift

Among a series of benzopyridone-based scaffolds investigated as human transient receptor potential vanilloid 1 (TRPV1) ligands, two isomeric benzopyridone scaffolds demonstrated a consistent and distinctive functional profile in which 2-oxo-1,2-dihydroquinolin-5-yl analogues (e.g., 2) displayed high affinity and potent antagonism, whereas 1-oxo-1,2-dihydroisoquinolin-5-yl analogues (e.g., 3) showed full agonism with high potency. Our computational models provide insight into the agonist-antagonist boundary of the analogues suggesting that the Arg557 residue in the S4-S5 linker might be important for sensing the agonist binding and transmitting signals. These results provide structural insights into the TRPV1 and the protein-ligand interactions at a molecular level.

Effects of the Distance between Radical Sites on the Reactivities of Aromatic Biradicals

Coupling of the radical sites in isomeric benzynes is known to hinder their radical reactivity. In order to determine how far apart the radical sites must be for them not to interact, the gas-phase reactivity of several isomeric protonated (iso)quinoline-and acridine-based biradicals was examined. All the (iso)quinolinium-based biradicals were found to react slower than the related monoradicals with similar vertical electron affinities (i.e., similar polar effects). In sharp contrast, the acridinium-based biradicals, most with the radical sites farther apart than in the (iso)quinolinium-based systems, showed greater reactivities than the relevant monoradicals with similar vertical electron affinities. The greater distances between the two radical sites in these biradicals lead to very little or no spin-spin coupling, and no suppression of radical reactivity was observed. Therefore, the radical sites can still interact if they are located on adjacent benzene rings and only after being separated further than that does no coupling occur. The most reactive radical site of each biradical was experimentally determined to be the one predicted to be more reactive based on the monoradical reactivity data. Therefore, the calculated vertical electron affinities of relevant monoradicals can be used to predict which radical site is most reactive in the biradicals.