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2-Bromo-3-chlorobenzoic acid

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Identification
Molecular formula
C7H4BrClO2
CAS number
6940-89-4
IUPAC name
2-bromo-3-chloro-benzoic acid;2-bromo-4-chloro-benzoic acid;2-bromo-6-chloro-benzoic acid;3-bromo-2-chloro-benzoic acid;3-bromo-5-chloro-benzoic acid;5-bromo-2-chloro-benzoic acid
State
State

At room temperature, 2-bromo-3-chlorobenzoic acid is typically found in a solid state. It is commonly available in a crystalline powder form, and due to its relatively high melting point, it maintains this state under ambient conditions.

Melting point (Celsius)
137.00
Melting point (Kelvin)
410.15
Boiling point (Celsius)
330.50
Boiling point (Kelvin)
603.50
General information
Molecular weight
235.45g/mol
Molar mass
235.4540g/mol
Density
1.9840g/cm3
Appearence

The compound exists generally as a solid. It is typically crystalline powder or solid form, color ranging from white to light yellow or off-white. The appearance may vary slightly depending on purity and form.

Comment on solubility

Solubility of 2-bromo-3-chloro-benzoic acid and related compounds

The solubility of halogenated benzoic acids, such as 2-bromo-3-chloro-benzoic acid, 2-bromo-4-chloro-benzoic acid, 2-bromo-6-chloro-benzoic acid, 3-bromo-2-chloro-benzoic acid, 3-bromo-5-chloro-benzoic acid, and 5-bromo-2-chloro-benzoic acid, is influenced by several factors related to their chemical structures. Here’s a detailed look at their solubility properties:

  • Polarity: The presence of halogen substituents generally increases the polarity of the benzoic acid derivatives, which can enhance their solubility in polar solvents like water.
  • Hydrogen Bonding: These compounds can participate in hydrogen bonding due to the carboxylic group (-COOH), which enhances solubility in water to some extent.
  • Halogen Effects: The location and type of halogen atoms can significantly alter the solubility. For instance, compounds with bromine and chlorine substituents tend to exhibit varied solubility patterns based on sterics and electronic effects.
  • Temperature Dependence: Like many organic acids, the solubility of these compounds typically increases with temperature, making them more soluble in warmer solutions.
  • Solvent Choices: While these compounds may have limited solubility in water, they often dissolve better in organic solvents such as ethanol, acetone, and DMSO due to their hydrophobic character from the aromatic rings.

In summary, the solubility of 2-bromo-3-chloro-benzoic acid and its analogs is multifaceted, influenced by both intrinsic structural factors and external conditions. Understanding these nuances is crucial for their practical applications in synthesis and analysis. As such, thorough experimentation is often required to ascertain their solubility under varying conditions.

Interesting facts

Interesting Facts about Bromo-Chloro Benzoic Acids

The family of compounds known as bromo-chloro benzoic acids represents a fascinating subset of aromatic carboxylic acids. Each isomer, including 2-bromo-3-chloro-benzoic acid, 2-bromo-4-chloro-benzoic acid, 2-bromo-6-chloro-benzoic acid, 3-bromo-2-chloro-benzoic acid, 3-bromo-5-chloro-benzoic acid, and 5-bromo-2-chloro-benzoic acid, offers unique properties and applications due to the distinct positioning of bromine and chlorine substituents on the benzene ring.

Key Characteristics

  • Substituent Effects: The placement of the bromine and chlorine atoms directly influences the compound’s reactivity and acidity. This makes them valuable for synthetic chemistry.
  • Pharmaceutical Applications: Some of these compounds have been studied for their potential applications in drug discovery and development, especially in targeting specific biological pathways.
  • Material Science: Bromo-chloro benzoic acids can be utilized in the synthesis of polymers and materials, where their halogen substituents impart specific properties, such as flame retardancy.
  • Research Significance: These compounds serve as intermediates in organic synthesis, utilized for creating more complex molecules with desirable biological properties.

One notable aspect is that, as with many halogenated compounds, they exhibit interesting solvation properties that can alter their behavior in various solvents, impacting their use in a wide array of chemical reactions.

Furthermore, the study of these compounds provides insights into the principles of chirality and stereochemistry, making them excellent candidates for educational purposes in both undergraduate and graduate chemistry courses. As we explore the intricate world of organic compounds, the bromo-chloro benzoic acids remind us of the elegance and complexity found within chemical structures.

Synonyms
Benzoic acid, bromochloro-
BROMOCHLOROBENZOIC ACID
H316500500
DTXSID10180322
2-bromo-3-chlorobenzoic acid;2-bromo-4-chlorobenzoic acid;2-bromo-6-chlorobenzoic acid;3-bromo-2-chlorobenzoic acid;3-bromo-5-chlorobenzoic acid;5-bromo-2-chlorobenzoic acid