Skip to main content

Anisidines

ADVERTISEMENT
Identification
Molecular formula
C7H9NO
CAS number
90-04-0 (2-methoxyaniline); 591-20-8 (3-methoxyaniline); 104-94-9 (4-methoxyaniline)
IUPAC name
2-methoxyaniline;3-methoxyaniline;4-methoxyaniline
State
State

At room temperature, anisidines are typically liquids. The exact state may vary slightly depending on the specific isomer, but generally, they remain liquid at standard conditions.

Melting point (Celsius)
-2.50
Melting point (Kelvin)
270.65
Boiling point (Celsius)
243.00
Boiling point (Kelvin)
516.15
General information
Molecular weight
123.16g/mol
Molar mass
123.1560g/mol
Density
1.0890g/cm3
Appearence

Anisidines are organic compounds with a benzene ring. Depending on the position of the methoxy group relative to the amino group, they can appear as colorless or slightly yellowish liquids. Over time, they may darken upon exposure to air and light due to oxidation.

Comment on solubility

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

The solubility of the methoxyaniline isomers—2-methoxyaniline, 3-methoxyaniline, and 4-methoxyaniline—exhibits some intriguing characteristics due to their structural differences. These compounds, which share a common amine and methoxy functional group, engage in distinctive solubility behaviors based on their positional isomerism.

General Solubility Insights

  • 2-Methoxyaniline: Typically, this isomer dissolves well in organic solvents such as ethanol and ether, while showing limited solubility in water. The electron-donating effect of the methoxy group enhances its solubility in non-polar solvents.
  • 3-Methoxyaniline: This isomer presents a moderate solubility in water owing to its molecular structure, but tends to dissolve readily in polar organic solvents. The slightly polar character created by the methoxy and amine groups contributes to this solubility profile.
  • 4-Methoxyaniline: Similar to its counterparts, 4-methoxyaniline is also more soluble in organic solvents compared to aqueous environments. The methoxy group, located para to the amine group, may help facilitate some hydrogen bonding with water, yet overall solubility remains low.

Factors Affecting Solubility

When considering the solubility of these compounds, several factors come into play:

  • Hydrogen Bonding: The capability of the amine group to form hydrogen bonds affects solubility in polar solvents.
  • Molecular Structure: The orientation of the methoxy group influences how the compounds interact with solvents.
  • Temperature: Higher temperatures generally increase solubility for many organic compounds, including the methoxyanilines.

Overall, while these isomers show notable trends in solubility due to their functional groups and structural arrangement, it’s essential to consider the specific solvent environment to fully understand their dissolving capacities.

Interesting facts

Interesting Facts about Methoxyanilines

The methoxyanilines, comprising 2-methoxyaniline, 3-methoxyaniline, and 4-methoxyaniline, are intriguing chemical compounds that play significant roles in various industrial and research applications. Here are some engaging facts about these compounds:

  • Structural Characteristics: Each methoxyaniline differs by the position of the methoxy group (-OCH3) relative to the amino group (-NH2). This subtle structural variation leads to distinct chemical properties and reactivities.
  • Applications: These compounds are widely utilized in the manufacture of dyes and pigments. They serve as intermediates in creating vibrant colors for textiles and other materials.
  • Pharmaceutical Relevance: Methoxyanilines have been explored for their potential biological activity, making them valuable in pharmaceutical research. They exhibit varying levels of biological activity, hinting at their potential use in drug development.
  • Environmental Concerns: While methoxyanilines are useful, their environmental impact is a growing concern. Understanding how they degrade and affect ecosystems is an essential area of research.
  • Historical Significance: The synthesis of methoxyanilines can be traced back to early organic chemistry studies, showcasing the evolution of techniques and methods within the field.

In summary, the methoxyanilines are more than just compounds; they represent a fascinating intersection of chemistry, industry, and environmental science. Their diverse applications highlight not only their importance in everyday products but also the need for responsible research and application in the modern world.