Definition: 2-Bromoanisole is an organobromine compound consisting of an anisole ring system (methoxybenzene) with a bromine atom substituted at the ortho position (carbon-2) of the benzene ring. Its molecular formula is C7H7BrO.
Overview: 2-Bromoanisole is used primarily as an intermediate in organic synthesis, particularly in pharmaceutical and agrochemical industries. It may serve as a building block in cross-coupling reactions, such as Suzuki or Heck reactions, due to the presence of the bromine atom, which is a viable leaving group under palladium-catalyzed conditions. The methoxy group offers electronic activation and regioselective control, making this compound useful in directed ortho-metalation strategies.
Etymology/Origin: The name "2-Bromoanisole" follows IUPAC nomenclature rules. "Anisole" refers to methoxybenzene, derived from the word "anise," as the compound occurs naturally in aniseed oil. The prefix "2-Bromo-" indicates substitution of a bromine atom at the second carbon position relative to the methoxy group on the benzene ring (i.e., ortho position).
Characteristics:
- Chemical formula: C7H7BrO
- Molar mass: 187.04 g/mol
- Appearance: Typically a colorless to pale yellow liquid
- Boiling point: Approximately 200–205 °C (reported values vary)
- Solubility: Insoluble in water; soluble in common organic solvents such as ethanol, ether, and dichloromethane
- Structure: Aromatic ring with a methoxy (–OCH3) group and a bromine (–Br) atom attached at adjacent positions (1,2-disubstituted benzene)
- Polarity: Moderately polar due to the presence of the electronegative bromine and oxygen atoms
Safety and handling: As with many brominated aromatic compounds, 2-bromoanisole should be handled with care. It may be harmful if inhaled, ingested, or absorbed through the skin. It is advisable to use appropriate personal protective equipment and work in a fume hood.
Related Topics:
- Anisole
- Organobromine compounds
- Electrophilic aromatic substitution
- Ortho-metalation
- Cross-coupling reactions
- Suzuki reaction
- Directed ortho functionalization
- Halogenated aromatic hydrocarbons
This compound is referenced in specialized chemical databases such as PubChem, ChemSpider, and SciFinder, and its synthesis and applications are documented in peer-reviewed organic chemistry literature.