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Clioquinol

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Identification
Molecular formula
C9H5Cl2NO
CAS number
130-26-7
IUPAC name
5-chloroquinolin-8-ol;7-chloroquinolin-8-ol;5,7-dichloroquinolin-8-ol
State
State

At room temperature, clioquinol is in a solid state. It is a crystalline powder with moderate stability under normal ambient conditions.

Melting point (Celsius)
172.00
Melting point (Kelvin)
445.00
Boiling point (Celsius)
270.00
Boiling point (Kelvin)
543.00
General information
Molecular weight
305.55g/mol
Molar mass
305.5520g/mol
Density
1.5583g/cm3
Appearence

Clioquinol is a pale yellow crystalline solid. It may have a mild, characteristic odor. The compound typically forms as fine powdery crystals used in various pharmaceutical and biological applications.

Comment on solubility

Solubility of Chlorinated Quinolinol Compounds

The solubility characteristics of the chlorinated quinolinol compounds, such as 5-chloroquinolin-8-ol, 7-chloroquinolin-8-ol, and 5,7-dichloroquinolin-8-ol, can be rather complex due to their unique chemical structures.

Factors Influencing Solubility

  • Hydrophobic Regions: The presence of chlorine atoms significantly affects solubility, introducing hydrophobic regions that can hinder its interaction with water.
  • Hydrogen Bonding: The hydroxyl group (–OH) on the quinoline structure may provide a means for hydrogen bonding with water, promoting some degree of solubility.
  • Polarity: Overall polarity depends on the balance between the hydrophilic (–OH) and hydrophobic (chlorine) components, often resulting in limited solubility in aqueous solutions.

In general, these compounds tend to exhibit moderate solubility in organic solvents like ethanol and acetone, while their solubility in polar solvents, such as water, is considerably lower. This dual characteristic underscores their behavior as amphiphilic compounds, where solubility varies widely based on the solvent used. Therefore, when handling these substances, it is essential to consider the solvent properties in both experimental and application contexts.

Key Observations

  • 5-chloroquinolin-8-ol: Moderate solubility in organic solvents but low solubility in water.
  • 7-chloroquinolin-8-ol: Similar trends as the 5-chloro derivative.
  • 5,7-dichloroquinolin-8-ol: Likely to exhibit lower solubility due to increased hydrophobicity from dual chlorine substitutions.

In summary, while chlorinated quinolinols have some polar features that may enhance their solubility in non-aqueous environments, their overall modest water solubility limits their usability in aqueous drug formulations.

Interesting facts

Interesting Facts about 5-Chloroquinolin-8-ol, 7-Chloroquinolin-8-ol, and 5,7-Dichloroquinolin-8-ol

Quinoline derivatives, particularly those like 5-chloroquinolin-8-ol, 7-chloroquinolin-8-ol, and 5,7-dichloroquinolin-8-ol, are fascinating compounds in the field of medicinal chemistry. Here are some captivating insights:

  • Antimalarial Properties: Many quinoline derivatives are historically noted for their role in antimalarial treatments. The structural modifications of these compounds can significantly impact their biological activity.
  • Research Potential: These specific chloroquinolines have been studied for their potential in combating various resistant strains of pathogens, marking their relevance in ongoing pharmaceutical research.
  • Fluorescence: Certain chloroquinolines exhibit interesting fluorescent properties, making them useful in biological imaging and as fluorescent probes in various assays.
  • Structural Diversity: Remarkably, the substitution patterns in the quinoline structure, such as the position of chlorine atoms, can lead to alterations in physicochemical properties and biological activity.
  • Mechanism of Action: These compounds can interfere with the nucleic acid synthesis of pathogens, showcasing a unique mechanism that continues to be a topic of extensive research.

In the ever-evolving landscape of medicinal chemistry, compounds like these are not just chemical entities; they represent potential pathways to new therapeutic discoveries. As chemists dive deeper into their mechanisms, we may uncover even more extraordinary applications in the fight against infectious diseases and beyond.

Conclusion

As we study the nuances of 5-chloroquinolin-8-ol, 7-chloroquinolin-8-ol, and 5,7-dichloroquinolin-8-ol, we are reminded of the importance of chemical diversity in the quest for innovative solutions in healthcare. The journey of understanding these compounds is a testament to the intricate relationship between chemistry and pharmacology.

Synonyms
HALQUINOLS
Halquinols [USAN]
UNII-Z7Z4BX535U
chlorhydroxyquinoline
SQ 16,401
DTXSID90230490
Halquinols (USAN)
SQ-16401
SO 16,401
HALQUINOL (MART.)
HALQUINOL [MART.]
5,7-Dichloro-8-quinolinol mixt. with 5-chloro-8-quinolinol and 7-chloro-8-quinolinol
8-Quinolinol, 5,7-dichloro-, mixt. with 5-chloro-8-quinolinol and 7-chloro-8-quinolinol
5,7-Dichloro-8-quinolinol, 5-chloro-8-quinolinol, and 7-chloro-8-quinolinol in proportions resulting naturally from chlorination of 8-quinolinol
Valpeda
Quinolor (TN)
HALQUINOL [MI]
HALQUINOL [WHO-DD]
DTXCID90152981
halquinol
5-chloroquinolin-8-ol;7-chloroquinolin-8-ol;5,7-dichloroquinolin-8-ol
Tarquinor
Z7Z4BX535U
CHEMBL3833358
MFCD28978222
5-chloroquinolin-8-ol; 7-chloroquinolin-8-ol; 5,7-dichloroquinolin-8-ol
SY272205
A839963
5,7-Dichloro-8-quinolino & 5-chloro-8-quinolino & 7-chloro-8-quinnolinol
5-chloro-8-quinolinol; 7-chloro-8-quinolinol; 5,7-dichloro-8-quinolinol
5,7-bis(chloranyl)quinolin-8-ol; 5-chloranylquinolin-8-ol; 7-chloranylquinolin-8-ol