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Chloroaniline Isomers

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Identification
Molecular formula
C6H6ClN
CAS number
615-36-5;108-42-9;106-47-8
IUPAC name
2-chloroaniline;3-chloroaniline;4-chloroaniline
State
State

Chloroaniline isomers are solid at room temperature.

Melting point (Celsius)
-2.00
Melting point (Kelvin)
271.15
Boiling point (Celsius)
230.00
Boiling point (Kelvin)
503.15
General information
Molecular weight
127.57g/mol
Molar mass
127.5700g/mol
Density
1.2000g/cm3
Appearence

The chloroaniline isomers consist of white to light brown crystals, which may appear as colorless solids depending on the purity.

Comment on solubility

Solubility of Chloroaniline Compounds

The solubility of chloroanilines, which include 2-chloroaniline, 3-chloroaniline, and 4-chloroaniline, can vary significantly due to their different molecular structures. Here are some key points to consider:

  • Polar Nature: Chloroanilines possess a polar amino group (–NH2) that can engage in hydrogen bonding with water, enhancing their solubility.
  • Chlorine Substitution: The position of the chlorine atom on the benzene ring influences solubility. Generally, these compounds show increased solubility in organic solvents.
  • pH Dependency: The solubility of chloroanilines is also dependent on the pH of the solution. They can become more soluble in basic conditions when protonation occurs, allowing them to exist as their corresponding cation.
  • Solvent Interactions: While they are moderately soluble in water, the presence of various solvents can alter their solubility profile significantly. For example, they often exhibit better solubility in alcohols and other organic solvents.

In summary, while 2-chloroaniline, 3-chloroaniline, and 4-chloroaniline display variability in solubility, they commonly exhibit moderate solubility in water and better solubility in organic solvents, particularly under varying pH conditions. Understanding these properties is crucial for their application and handling in various chemical processes.

Interesting facts

Exploring Chloroanilines: 2-Chloroaniline, 3-Chloroaniline, and 4-Chloroaniline

Chloroanilines are an important class of aromatic amines that contain both a chloro group and an amino group. Representing **substituted anilines**, each positional isomer—2-chloroaniline, 3-chloroaniline, and 4-chloroaniline—has unique properties and applications:

  • Industrial Relevance: These compounds are crucial in the synthesis of various dyes, pharmaceuticals, and agrochemicals. For instance, they serve as essential intermediates in the production of azo dyes.
  • Positional Influence: The position of the chlorine atom significantly influences the chemical reactivity. This positional isomerism leads to varied physical and chemical properties across the three isomers.
  • Toxicological Profile: Safety is a primary concern when handling these compounds, as they can pose risks to human health. Appropriate safety precautions are necessary, including protective gear and proper ventilation during handling.
  • Environmental Impact: These compounds can be harmful to aquatic life and may persist in the environment, necessitating careful disposal methods to mitigate ecological risks.
  • Research Applications: Beyond their industrial uses, chloroanilines are subjects of ongoing research, particularly in the fields of medicinal chemistry and materials science, where their unique properties can lead to novel findings.

Conclusion

The chloroanilines exemplify the diverse world of organic compounds, showcasing how minor structural differences can lead to significant variations in properties and applications. As students and chemists delve deeper into the world of these isomers, the potential for innovation in both existing fields and emerging domains becomes more apparent. Understanding these compounds not only expands scientific knowledge but also emphasizes the importance of chemical safety and environmental stewardship.