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Dichloroaniline

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Identification
Molecular formula
C6H5Cl2N
CAS number
608-27-5 (for 2,3-Dichloroaniline); 554-00-7 (for 2,4-Dichloroaniline); 608-31-1 (for 2,6-Dichloroaniline); 95-76-1 (for 3,4-Dichloroaniline); 95-82-9 (for 3,5-Dichloroaniline)
IUPAC name
2,3-dichloroaniline;2,4-dichloroaniline;2,6-dichloroaniline;3,4-dichloroaniline;3,5-dichloroaniline
State
State
At room temperature, dichloroaniline compounds are typically solid if they are pure and correctly isolated from any solvent or water. The state may vary among the isomers.
Melting point (Celsius)
32.00
Melting point (Kelvin)
305.15
Boiling point (Celsius)
238.00
Boiling point (Kelvin)
511.15
General information
Molecular weight
163.00g/mol
Molar mass
162.9980g/mol
Density
1.3674g/cm3
Appearence

Dichloroaniline may appear as crystalline solid or liquid depending on the isomer and specific conditions such as temperature. It may also vary in color from colorless to pale yellowish. The different isomers can have slightly different physical appearances as well.

Comment on solubility

Solubility of Dichloroanilines

The solubility of dichloroanilines, which include compounds such as 2,3-dichloroaniline, 2,4-dichloroaniline, 2,6-dichloroaniline, 3,4-dichloroaniline, and 3,5-dichloroaniline, is influenced by several factors:

  • Polar Nature: These compounds contain both polar (amine) and non-polar (aromatic ring) characteristics, which affects their interaction with solvents.
  • Chlorine Substitution: The presence of chlorine atoms increases the *polarity* of the aniline structure, enhancing their solubility in polar solvents such as water.
  • Hydrogen Bonding: The amino group (-NH2) can form hydrogen bonds with water molecules, contributing to increased solubility.

As a general rule, the solubility order can vary, typically reflecting the position of the chlorine substituents on the aromatic ring:

  1. 2,4-dichloroaniline tends to show higher solubility due to optimal hydrogen bonding capabilities.
  2. 2,3- and 2,6-dichloroaniline also exhibit notable solubility, albeit slightly lower than 2,4-dichloroaniline.
  3. 3,4-dichloroaniline can have reduced solubility due to steric hindrance.
  4. 3,5-dichloroaniline may show the least solubility among the series due to increased non-polar character.

In conclusion, the solubility of dichloroanilines is a nuanced concept that is affected by chemical structure and environmental interactions, allowing these compounds to dissolve effectively in various solvents.

Interesting facts

Interesting Facts about Dichloroanilines

Dichloroanilines comprise a group of chemical compounds that are derived from aniline, featuring *two chlorine* atoms attached to the benzene ring at varying positions. The most notable examples are 2,3-dichloroaniline, 2,4-dichloroaniline, 2,6-dichloroaniline, 3,4-dichloroaniline, and 3,5-dichloroaniline. Here are some intriguing highlights about these compounds:

  • Versatile Applications: Dichloroanilines are used as intermediates in the synthesis of various dyes, pesticides, and pharmaceutical compounds, showcasing their importance in industrial chemistry.
  • Structural Diversity: Each dichloroaniline variant exhibits unique properties and reactivity due to the difference in the positioning of chlorine atoms on the aromatic ring, influencing their behavior in chemical reactions.
  • Environmental Considerations: While some dichloroanilines are valuable in industry, they also pose challenges in terms of environmental health, as some can be harmful to aquatic life and may require careful management and remediation strategies.
  • Biological Activity: Several studies have demonstrated that dichloroanilines possess biological activity, including potential antibacterial and antifungal properties, making them subjects of research in the medical field.
  • Reactivity Profile: Different substitutions on the aniline ring can lead to varied reactivity with electrophiles and nucleophiles, which is a cornerstone for the development of new chemical entities in organic synthesis.

In summary, the dichloroanilines are a fascinating collection of compounds not only due to their diverse range of applications but also because of their significant implications in both industry and environmental science. As researchers continue to explore the unique properties and potential uses of these compounds, their impact on various fields will undoubtedly expand.