4'-Bromoheptanophenone

1-Bromo-4-n-heptanoylbenzene (CAS: 99474-02-9), also known as 4'-Bromoheptanophenone or 1-(4-Bromophenyl)heptan-1-one, is an important organic compound widely utilized in pharmaceutical research, organic synthesis, and materials science . Its molecular formula is C₁₃H₁₇BrO, with a molecular weight of 269.18 g/mol.

Physical and Chemical Properties

The compound appears as a white to off-white crystalline solid with a melting point range of 69-72°C . It has a predicted boiling point of 337.1°C at 760 mmHg, a density of 1.225 g/cm³, and a flash point of 36.4°C . The molecule contains 6 rotatable bonds, zero hydrogen bond donors, and one hydrogen bond acceptor, with a topological polar surface area of 17.07 Ų . The calculated LogP value of approximately 4.6 indicates moderate to high lipophilicity, making the compound readily soluble in organic solvents such as dichloromethane, ethyl acetate, and toluene .

Structural Features

The molecule consists of a benzene ring substituted with a bromine atom at the 1-position and a heptanoyl group (-CO-(CH₂)₅CH₃) at the 4-position. This unique substitution pattern combines an electron-withdrawing ketone functionality with a halogen leaving group, providing two distinct reactive sites for subsequent chemical transformations .

Synthetic Utility and Applications

1-Bromo-4-n-heptanoylbenzene serves as a valuable building block in organic synthesis. The bromine atom enables participation in palladium-catalyzed cross-coupling reactions including Suzuki-Miyaura, Buchwald-Hartwig, and Sonogashira couplings, allowing for the introduction of various aryl, amino, or alkynyl groups . The ketone group can undergo nucleophilic addition reactions, reductions to alcohols, or condensations with hydrazines and hydroxylamines to form heterocyclic compounds. These properties make it an important intermediate for pharmaceutical development, particularly in the synthesis of kinase inhibitors and other biologically active molecules. Some suppliers list its application as a catalyst or catalyst precursor .

Safety and Handling

The compound is classified as an irritant (Xi) with hazard statements H315 (causes skin irritation), H319 (causes serious eye irritation), and H335 (may cause respiratory irritation) . Safety precautions include using P261 (avoid breathing dust/fume/gas/mist/vapors/spray), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes), and P302+P352 (IF ON SKIN: Wash with plenty of water) . It should be stored in a cool, dry, well-ventilated area, sealed at room temperature, away from strong oxidizing agents and bases .

Specifications

Commercial grades are available at 97-98% purity, with typical packaging sizes of 1g, 5g, and larger quantities for research and industrial applications .