2-Bromo-5-chlorophenol is a halogenated aromatic compound widely studied for its role as an intermediate in organic synthesis and chemical research. With both bromine and chlorine substituents attached to a phenolic ring, this compound exhibits unique structural characteristics and chemical reactivity, making it relevant in pharmaceuticals, agrochemicals, and material sciences.
IUPAC Name: 2-Bromo-5-chlorophenol
Molecular Formula: C₆H₄BrClO
Molecular Weight: 207.45 g/mol
CAS Number: 13659-23-9
The compound consists of a benzene ring substituted with:
A hydroxyl group (-OH) at position 1
A bromine atom at position 2
A chlorine atom at position 5
This arrangement influences both the electronic distribution of the aromatic ring and the compound’s reactivity.
Appearance: Off-white to light brown crystalline solid
Melting Point: ~63–67 °C (varies slightly with purity)
Boiling Point: Decomposes before boiling
Solubility: Moderately soluble in organic solvents such as ethanol, chloroform, and acetone; limited solubility in water
The presence of two electronegative halogens alongside the hydroxyl group alters intermolecular interactions, influencing solubility and stability.
Halogen Reactivity
The bromine and chlorine substituents make the compound reactive toward nucleophilic substitutions and cross-coupling reactions (e.g., Suzuki or Heck reactions).
Phenolic Group Reactivity
The hydroxyl group confers weak acidity and hydrogen bonding ability, enabling esterification, etherification, and oxidative transformations.
Stability
Stable under ambient conditions, but prolonged exposure to heat or strong oxidizing agents may lead to decomposition.
Synthetic Intermediate: Used in the preparation of pharmaceuticals and bioactive molecules.
Agrochemical Research: Can serve as a precursor in the synthesis of herbicides, fungicides, or insecticides.
Material Science: Occasionally explored in polymer and dye chemistry due to its reactive halogenated aromatic core.
Classified as harmful if ingested or inhaled.
May cause skin and eye irritation.
Handle with protective gloves, goggles, and adequate ventilation in laboratory settings.
2-Bromo-5-chlorophenol (CAS: 13659-23-9) is a versatile halogenated phenol with distinct structural features and reactive sites. Its combination of bromine, chlorine, and hydroxyl functionalities makes it an important intermediate in organic synthesis, bridging research applications across pharmaceuticals, agrochemicals, and specialty chemicals.
