Tadalafil | Solubility of Things

Identification

Molecular formula

C₂₂H₁₉N₃O₄

CAS number

171596-29-5

IUPAC name

[4-[(dimethylamino)methyl]-5-hydroxy-benzofuran-3-yl]-(2,4-dimethylphenyl)methanone

State

At room temperature, tadalafil is a solid.

Melting point (Celsius)

301.20

Melting point (Kelvin)

574.30

Boiling point (Celsius)

540.30

Boiling point (Kelvin)

813.30

General information

Molecular weight

389.40g/mol

Molar mass

389.4040g/mol

Density

1.4050g/cm³

Appearence

Tadalafil appears as a white to off-white crystalline solid.

Comment on solubility

Solubility of [4-[(dimethylamino)methyl]-5-hydroxy-benzofuran-3-yl]-(2,4-dimethylphenyl)methanone

The solubility of the compound [4-[(dimethylamino)methyl]-5-hydroxy-benzofuran-3-yl]-(2,4-dimethylphenyl)methanone can be quite intriguing, influenced by both its molecular structure and the functional groups present. Here are some critical considerations regarding its solubility:

Polar and Non-Polar Characteristics: This compound contains both polar (hydroxyl and dimethylamino groups) and non-polar (benzofuran and dimethylphenyl) functional groups, which can affect solubility in different solvents.
Solvent Compatibility: It may exhibit solubility in polar organic solvents such as methanol or ethanol due to its polar functional groups, while being less soluble in non-polar solvents like hexane.
Hydrogen Bonding: The presence of the hydroxyl group allows for potential hydrogen bonding, enhancing solubility in polar environments, but possibly reducing solubility in strictly non-polar solvents.
pH Dependence: Variations in pH of the solution may affect the solubility of the compound, particularly affecting the protonation state of the dimethylamino group.

In conclusion, while the exact solubility can depend on various factors, it is likely that this compound demonstrates moderate solubility in polar solvents and lower solubility in non-polar environments. "Understanding the solubility characteristics is crucial for applications in synthesis and formulation."

Interesting facts

Interesting Facts about [4-[(dimethylamino)methyl]-5-hydroxy-benzofuran-3-yl]-(2,4-dimethylphenyl)methanone

This intriguing compound is a member of the benzofuran family, which is notable for its diverse range of biological activities. Here are some fascinating aspects to consider:

Biological Significance: Compounds containing the benzofuran structure have been researched for various pharmacological effects, including anti-inflammatory and antitumor properties. This particular compound may provide insights into potential medicinal applications.
Complex Structure: The intricate design of this compound, featuring both dimethylamino and hydroxyl groups, suggests the possibility of unique interactions within biological systems, hinting at a role in neurotransmission or receptor binding.
Research Potential: Due to its unique chemical structure, this compound can serve as a valuable lead structure in drug development, especially in the realm of organic synthesis and medicinal chemistry.
Photophysical Properties: The benzofuran moiety can exhibit interesting photophysical properties, making this compound a subject of interest for researchers in fields such as photochemistry and optoelectronic applications.
Synthetic Versatility: This compound can be synthesized through various methods, which may involve different chemical reactions such as alkylation, acylation, and functional group interconversions, offering a rich ground for experimental exploration.

In summary, the compound [4-[(dimethylamino)methyl]-5-hydroxy-benzofuran-3-yl]-(2,4-dimethylphenyl)methanone embodies a wealth of research opportunities, marrying complexity with potential functionality in various chemical and biological contexts.