Introduction to 2-Bromo-4'-methylpropiophenone

2-Bromo-4'-methylpropiophenone (CAS: 1451-82-7) is a brominated aromatic ketone widely recognized for its role as a versatile building block in organic synthesis. Its molecular structure, featuring a reactive bromine atom and a methyl-substituted phenyl ring, enables selective functionalization, making it invaluable for constructing complex molecules in pharmaceuticals, agrochemicals, and specialty chemicals.

Chemical Properties and Reactivity

This compound exhibits distinct reactivity due to its electron-withdrawing carbonyl group and bromine substituent, which facilitate nucleophilic substitution and cross-coupling reactions. Key properties include:

• Molecular Formula: C10H11BrO
• Melting Point: 48-52°C
• Boiling Point: 285-287°C
• Solubility: Soluble in organic solvents like ethanol, acetone, and dichloromethane.

Applications in Organic Synthesis

Pharmaceutical Intermediates

2-Bromo-4'-methylpropiophenone serves as a precursor for active pharmaceutical ingredients (APIs), particularly in synthesizing antipsychotics and anti-inflammatory agents. Its bromine atom participates in Suzuki-Miyaura and Heck couplings to introduce aryl or vinyl groups.

Synergy with γ-Butyrolactone (GBL)

When combined with γ-butyrolactone, this compound enables innovative pathways for heterocyclic synthesis. GBL acts as a solvent and reagent, facilitating ring-opening reactions to produce pyrrolidones and other N-heterocycles—key motifs in drug design.

Advantages Over Alternatives

Compared to similar brominated ketones, 2-Bromo-4'-methylpropiophenone offers:

• Higher selectivity in electrophilic aromatic substitution.
• Improved yield in palladium-catalyzed reactions.
• Lower toxicity profile than brominated benzenes.

Quality and Handling

To ensure optimal performance, store the compound in a cool, dry place under inert conditions. Purity (>98%) is critical for reproducible results in sensitive reactions. Always use personal protective equipment (PPE) due to its mild irritant properties.

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