5-CHLORO-8-HYDROXYQUINOLINE

Colorless or light yellow solid, soluble in organic solvents such as ethanol, chloroform and dichloromethane.

Used in organic synthesis, pesticide intermediates.

5-Chloro-8-hydroxyquinoline is an organic chemical compound with a variety of applications, particularly in the fields of biochemistry, medicine, and materials science. It is a derivative of quinoline, a heterocyclic compound, and is characterized by the presence of a chlorine atom at the 5-position and a hydroxyl group at the 8-position of the quinoline ring structure. This compound exhibits a broad range of biological and chemical activities.

Chemical Characteristics

Applications

1. Antimicrobial Agent:
   5-Chloro-8-hydroxyquinoline is known for its antimicrobial properties and is often used in medical and pharmaceutical formulations as an antimicrobial agent. It is particularly effective against certain bacteria and fungi, making it useful in disinfectants and topical treatments for skin infections.

2. Anticorrosive Agent:
   Due to its ability to chelate metal ions, it is used in industrial applications as an anticorrosive agent. It can be found in some formulations designed to prevent metal corrosion in various systems, including water treatment processes.

3. Biochemical Research:
   This compound is used in laboratory settings for its role in inhibiting metalloproteins and enzymes, particularly in studies related to biochemistry and cellular metabolism. It acts as a chelator, binding to metal ions in enzymes and disrupting their activity.

4. Dye and Fluorescent Marker:
   5-Chloro-8-hydroxyquinoline is sometimes employed as a component in fluorescent dyes and markers. Its fluorescence properties make it useful for tagging biomolecules in microscopy and other analytical techniques.

5. Photochemistry and Material Science:
   It is used in the development of photoactive materials, including those in solar cells and optoelectronic devices, due to its electronic properties.

Mode of Action

The antimicrobial action of 5-chloro-8-hydroxyquinoline is believed to occur through its ability to bind to metal ions, particularly iron and copper, which are essential for the growth and proliferation of certain microorganisms. By chelating these metals, the compound can disrupt microbial metabolic processes, thereby inhibiting their growth.

In industrial applications, the compound’s ability to chelate metal ions also plays a role in preventing the oxidation and corrosion of metals, particularly in water-based systems.

Safety and Handling

While 5-chloro-8-hydroxyquinoline is generally considered safe when used appropriately, it should be handled with caution to avoid potential health hazards:

• Protective Gear: Wear gloves, goggles, and other personal protective equipment (PPE) to avoid skin and eye contact.

• Storage: Store in a cool, dry place away from incompatible materials. Keep it in tightly sealed containers to prevent moisture absorption and degradation.

• Disposal: Dispose of according to local environmental and safety regulations. Avoid releasing it into the environment due to its potential toxicity.

Health Hazards:

• Inhalation: May cause irritation to the respiratory system. Ensure good ventilation when handling the compound.

• Skin and Eye Contact: Can cause irritation. In case of exposure, rinse immediately with water.

• Ingestion: Ingestion of the compound may result in gastrointestinal upset. Seek medical attention immediately if ingested.

Conclusion

5-Chloro-8-hydroxyquinoline is a versatile compound with antimicrobial, anticorrosive, and chelating properties. It has found use in a variety of applications, including pharmaceutical formulations, industrial anticorrosion treatments, and as a research tool in biochemistry. As with all chemicals, it should be handled with care, and safety protocols should be followed to minimize health risks and environmental impact.

FAQ

1. What is the primary use of 5-chloro-8-hydroxyquinoline?
It is primarily used as an antimicrobial agent, but also serves in anticorrosive applications, biochemical research, and as a fluorescent marker.

2. Is 5-chloro-8-hydroxyquinoline safe to handle?
It is generally safe when used properly. Protective equipment should be worn to avoid direct skin or eye contact. Ensure good ventilation when handling the compound.

3. How should 5-chloro-8-hydroxyquinoline be stored?
Store in a cool, dry place, away from moisture and incompatible materials, in tightly sealed containers.

4. What are the health hazards associated with 5-chloro-8-hydroxyquinoline?
It may cause irritation to the skin, eyes, or respiratory system if improperly handled. Ingestion or inhalation can lead to health issues, so proper handling precautions should be followed.

5. Can 5-chloro-8-hydroxyquinoline be used in food products?
It is not typically used in food products due to its antimicrobial nature and potential toxicity. It is more commonly used in industrial or medical applications.