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2,4,6-Tribromophenol

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Identification
Molecular formula
C6H3Br3O
CAS number
118-79-6
IUPAC name
2,3,4-tribromophenol;2,3,5-tribromophenol;2,4,5-tribromophenol;2,4,6-tribromophenol;3,4,5-tribromophenol
State
State

At room temperature, 2,4,6-tribromophenol is in solid state. It is typically a crystalline powder that can be handled under normal laboratory conditions. Due to its halogenated nature, it is less volatile than its non-brominated counterpart.

Melting point (Celsius)
92.50
Melting point (Kelvin)
365.65
Boiling point (Celsius)
281.50
Boiling point (Kelvin)
554.65
General information
Molecular weight
330.81g/mol
Molar mass
330.8080g/mol
Density
2.9000g/cm3
Appearence

2,4,6-Tribromophenol appears as a white to slightly off-white crystalline solid. It is often encountered as a powder with a characteristic phenolic odor.

Comment on solubility

Solubility of Tribromophenols

The solubility of tribromophenols exhibits interesting characteristics due to the presence of bromine atoms, which enhance the hydrophobic properties of the compounds. Here are some key points regarding their solubility:

  • Water Solubility: Tribromophenols generally have low to moderate solubility in water. The presence of multiple bromine atoms can impede aqueous solvation.
  • Organic Solvents: These compounds are more soluble in organic solvents, such as ethanol, acetone, and chloroform, making them useful for various organic applications.
  • Temperature Dependence: Solubility can be influenced by temperature; typically, solubility increases with an increase in temperature, which is critical for applications requiring higher concentrations.
  • Structural Variation: The specific orientation and position of bromine substituents on the phenol ring (e.g., at the 2, 3, or 4 positions) can affect both the hydrophobicity and solubility profile.

In summary, while tribromophenols are not particularly soluble in water, their solubility patterns in organic solvents and response to temperature changes highlight the intricate balance between molecular structure and solvation properties. As noted, "the presence of halogens generally results in significant modulation of solubility characteristics."

Interesting facts

Interesting Facts about Tribromophenols

Tribromophenols are a fascinating class of chemical compounds that derive from phenol through the substitution of bromine atoms. The compounds mentioned, namely 2,3,4-tribromophenol, 2,3,5-tribromophenol, 2,4,5-tribromophenol, 2,4,6-tribromophenol, and 3,4,5-tribromophenol, showcase different variations in the positioning of bromine atoms on the phenolic ring, leading to unique properties and applications.

Characteristics and Applications

  • Biocidal Properties: Many tribromophenols possess effective biocidal properties, making them useful in various antifungal and antibacterial applications.
  • Industrial Uses: These compounds are commonly used as flame retardants, highlighting their significance in enhancing safety measures in materials that are prone to ignition.
  • Environmental Considerations: It's crucial to note that certain tribromophenols can be persistent and toxic in the environment, prompting discussions on their regulation and safe handling practices.
  • Analytical Chemistry: The intriguing reactivity of tribromophenols lends itself to analytical applications, where they can be used as substrates in various organic reactions, contributing to the development of new chemical methodologies.

Chemical Behavior

The varying positions of the bromine substituents influence the electronic distribution within the molecule, leading to differences in reactivity and stability. For instance, 2,4,6-tribromophenol, with bromine atoms all situated in the ortho and para positions, exhibits heightened acidity compared to other isomers. This enhanced acidity is crucial for its role in various nucleophilic substitution reactions, which are fundamental in organic synthesis.

Quotes to Reflect On

As Richard Feynman once said, “The beauty of a flower is in the interaction of rays of light on it.” Similarly, the beauty of tribromophenols lies in:

  • Their intricate structure
  • Their broad applicability in chemistry and industry
  • The ongoing research aimed at better understanding their environmental impact

In summary, tribromophenols contribute significantly to both industrial applications and scientific research, serving as important subjects of study in the fields of chemistry and environmental science.