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o-cumenol, m-cumenol, p-cumenol

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Identification
Molecular formula
C9H12O
CAS number
499-75-2, 618-61-1, 645-56-7
IUPAC name
2-isopropylphenol;3-isopropylphenol;4-isopropylphenol
State
State

At room temperature, all three isomers, 2-isopropylphenol, 3-isopropylphenol, and 4-isopropylphenol, are typically in a liquid state under standard conditions.

Melting point (Celsius)
16.00
Melting point (Kelvin)
289.15
Boiling point (Celsius)
214.00
Boiling point (Kelvin)
487.15
General information
Molecular weight
136.19g/mol
Molar mass
136.1930g/mol
Density
0.9612g/cm3
Appearence

2-Isopropylphenol (o-Cumenol) is a colorless to pale yellow liquid.

3-Isopropylphenol (m-Cumenol) also typically appears as a colorless to pale yellow liquid.

4-Isopropylphenol (p-Cumenol) shows a similar appearence and is a colorless to pale yellow liquid as well.

Comment on solubility

Solubility of Isopropylphenol Compounds

The solubility characteristics of the isopropylphenol isomers, namely 2-isopropylphenol, 3-isopropylphenol, and 4-isopropylphenol, display some interesting trends due to their structural variations.

General Solubility Trends

In general, the positions of the isopropyl group relative to the hydroxyl group (OH) significantly influence the solubility in water:

  • 2-isopropylphenol: This isomer typically exhibits moderate solubility in water, benefiting from the proximity of the hydrophilic hydroxyl group to the hydrophobic isopropyl group, which can affect its interactions.
  • 3-isopropylphenol: Known for having lower solubility compared to its ortho counterpart, factors such as steric hindrance contribute to its less favorable interaction with water molecules.
  • 4-isopropylphenol: This para isomer tends to have the lowest water solubility, primarily due to the further distance between the isopropyl group and the hydroxyl group, which leads to a more hydrophobic character overall.

Key Influencing Factors

Several key factors influence the solubility of these compounds:

  1. Hydrophobic vs. Hydrophilic Balance: The larger isopropyl group increases hydrophobicity, while the hydroxyl group provides a hydrophilic component.
  2. Molecular Structure: The position of the hydroxyl group in relation to the isopropyl group affects steric hindrance and hydrogen bonding capacities with water.
  3. Temperature: Increased temperature often enhances solubility by providing additional energy to disrupt intermolecular forces.

Ultimately, while isopropylphenol compounds have similarities in structure, their varying solubility reflects the delicate interplay of molecular interactions that dictate their behavior in aqueous environments. Understanding these aspects is crucial for applications in chemical formulations, pharmaceuticals, and more.

Interesting facts

Interesting Facts about Isopropylphenols

The isopropylphenols, including 2-isopropylphenol, 3-isopropylphenol, and 4-isopropylphenol, are intriguing compounds in the realm of organic chemistry. These compounds belong to a class of aromatic organic compounds known for their unique structures and diverse applications. Below are some noteworthy points about the isopropylphenols:

  • Structural Variants: These compounds differ by the position of the isopropyl group on the phenolic ring, leading to variations in their chemical properties and reactivity.
  • Biological Activities: Some studies suggest that isopropylphenols exhibit interesting biological activities, including antibacterial and antifungal properties, making them valuable in medicinal chemistry.
  • Industrial Applications: They find applications in the synthesis of various dyes, fragrances, and preservatives, showcasing their versatility in the chemical industry.
  • Research Significance: Their reactivity and the ability to act as intermediates in synthetic processes make these compounds of great interest in academic research and industrial applications.

According to chemists, the positioning of substituents on the aromatic ring can significantly influence the overall properties of these compounds. As one researcher put it, “The subtleties of aromatic chemistry can open doors to innovative applications in both pharmaceuticals and materials science.”

In summary, the isopropylphenols exemplify the complex interplay between structure and function in organic chemistry, paving the way for continued exploration in both research and industry.