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Chlorophenol

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Identification
Molecular formula
C6H5ClO
CAS number
108-43-0, 591-35-5, 106-48-9
IUPAC name
2-chlorophenol;3-chlorophenol;4-chlorophenol
State
State

2-Chlorophenol and 3-Chlorophenol can be found as a liquid at room temperature, whereas 4-Chlorophenol is often found as a crystalline solid.

Melting point (Celsius)
42.00
Melting point (Kelvin)
315.00
Boiling point (Celsius)
175.00
Boiling point (Kelvin)
448.00
General information
Molecular weight
128.56g/mol
Molar mass
128.5610g/mol
Density
1.2680g/cm3
Appearence

2-Chlorophenol is a colorless to amber liquid with a sharp, medicinal odor. 3-Chlorophenol is a light amber liquid or crystalline solid. 4-Chlorophenol appears as a colorless to white crystalline solid or liquid and has a medicinal odor.

Comment on solubility

Solubility of 2-chlorophenol, 3-chlorophenol, and 4-chlorophenol

The solubility of chlorophenols in water varies among the isomers, influenced by both the position of the chlorine substituent and the molecular structure. Here’s a closer look at each compound's solubility characteristics:

  • 2-chlorophenol: This compound has moderate solubility in water, typically around 1.8 g per 100 mL at room temperature. Its solubility is attributed to the presence of a hydroxyl group that allows for hydrogen bonding with water molecules.
  • 3-chlorophenol: Similar to its isomer, 3-chlorophenol exhibits relatively high solubility, around 3.4 g per 100 mL at 25°C. The specific spatial arrangement of the chlorine atom contributes to its ability to interact favorably with water.
  • 4-chlorophenol: This isomer shows the greatest water solubility of the three, approximately 4.9 g per 100 mL at ambient temperature. The para position of the chlorine atom enhances its solvation processes significantly.

Factors that influence the solubility of these compounds include:

  • **Molecular polarity**: The more polar a molecule, the greater its tendency to dissolve in polar solvents like water.
  • **Hydrogen bonding**: The presence and position of the hydroxyl (-OH) group play a crucial role in solubility.
  • **Substituent effects**: The position of chlorine affects both the electronic distribution in the molecule and, consequently, its interaction with water.

In summary, the solubility of 2-chlorophenol, 3-chlorophenol, and 4-chlorophenol varies appreciably based on isomeric differences, highlighting the significant impact of structural factors on solubility. Understanding these nuances is essential when considering their applications in various chemical processes.

Interesting facts

Interesting Facts About Chlorophenols

Chlorophenols are an intriguing class of compounds that have drawn the attention of chemists due to their unique properties and applications. Among them, 2-chlorophenol, 3-chlorophenol, and 4-chlorophenol are particularly noteworthy for their structural differences and consequent chemical behaviors.

1. Structural Isomers

The differing locations of the chlorine atom in the phenolic ring create three distinct isomers:

  • 2-chlorophenol: The chlorine atom is located ortho to the hydroxyl group, influencing its reactivity and hydrogen bonding capabilities.
  • 3-chlorophenol: The chlorine is positioned meta, affecting the compound's overall polarity and solubility in various solvents.
  • 4-chlorophenol: Here, the chlorine is para to the hydroxyl group, making it the most stable isomer and commonly used in industrial applications.

2. Applications and Uses

Chlorophenols are versatile, finding applications across various industries:

  • They are utilized in the synthesis of pesticides and herbicides, aiding in agricultural productivity.
  • Due to their antibacterial properties, chlorophenols are often used as antiseptics in medicinal formulations.
  • These compounds also find use in the production of dyes and resins, showcasing their importance in the textile and materials industries.

3. Environmental Considerations

While chlorophenols play a significant role in industrial applications, they are also a subject of environmental concern:

  • Many chlorophenols are classified as environmental pollutants due to their potential toxicity and persistence in the environment.
  • They can bioaccumulate in aquatic life, posing risks to ecosystems and human health.

4. Safety Considerations

Handling chlorophenols requires caution:

  • They can cause skin and respiratory irritation; thus, wearing appropriate protective gear is advisable.
  • Ingestion or inhalation may lead to serious health concerns, emphasizing the need for proper safety protocols in laboratory settings.

To conclude, chlorophenols are more than just simple aromatic compounds; their unique structural characteristics, combined with their various applications, make them a key focus in both industrial chemistry and environmental science. As chemists, understanding these compounds helps us navigate their usage responsibly while minimizing environmental impact.

Synonyms
SCHEMBL27814172