6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE

6-Bromo-3,4-dihydro-1H-quinolin-2-one is a versatile organic synthesis intermediate and pharmaceutical intermediate primarily used in laboratory research and chemical production processes. The compound belongs to the quinolinone class of derivatives, which are known for their diverse biological activities and pharmaceutical relevance. 6-Bromo-3,4-dihydro-1H-quinolin-2-one has gained significant attention in the scientific community due to its potential therapeutic and environmental applications. The bromine atom at the 6-position provides a reactive handle for palladium-catalyzed cross-coupling reactions, enabling the synthesis of diverse quinolinone derivatives. 6-Bromo-3,4-dihydro-1H-quinolin-2-one has also demonstrated antifungal properties, suggesting potential applications in the treatment of fungal infections. Additionally, 6-Bromo-3,4-dihydro-1H-quinolin-2-one has been investigated as a precursor for inhibitors of human aldosterone synthase CYP11B2, highlighting its relevance in drug discovery programs targeting cardiovascular and endocrine disorders.

Product Parameters

Synthetic Route

Dissolve 3,4-dihydroquinoline-2(1H)-ketone (2.73 g, 18.55 mmol) in N,N-dimethylacetamide (30 mL), and slowly add under a water bath the solution of N-bromobutyryl imide (3.30 g, 18.55 mmol) in N,N-dimethylacetamide (10 mL). Continue stirring the reaction mixture under a water bath for 6 hours, then raise the temperature to room temperature and allow the reaction to proceed for an additional 12 hours. After completion, add water (50 mL) to the mixture and extract with ethyl acetate (50 mL × 3). Combine the organic phases, dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (v/v) = 3/1, yielding the target compound as a white solid (3.86 g, 92.1%).

 FAQ

Q1: What biological activities are associated with this compound?

A: Quinolinone derivatives, including 6-Bromo-3,4-dihydro-1H-quinolin-2-one, are known for diverse biological activities including antitumor, antimicrobial, antifungal, antiviral, antioxidant, anti-inflammatory, and anticoagulant properties. This compound has specifically demonstrated antifungal activity.

Q2: Is this compound hazardous?

A: 6-Bromo-3,4-dihydro-1H-quinolin-2-one is classified with hazard statements H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Signal word: Warning. Use in a fume hood with appropriate PPE—lab coat, safety goggles, and chemical-resistant gloves. Refer to the Safety Data Sheet (SDS) for complete safety information.

Storage Conditions

Store 6-Bromo-3,4-dihydro-1H-qui

nolin-2-one in a tightly sealed container, protected from light, in a dry environment at room temperature. Keep the container in a dark place as the compound is light sensitive. Store in a clean, well-ventilated area away from strong oxidizing agents, strong bases, and sources of ignition. The solid is stable under recommended storage conditions.

Shelf life: 2 years when stored in a sealed container in a dark, dry place at room temperature.

Handling precautions: Use only in a fume hood. Wear chemical-resistant gloves, safety goggles, and a lab coat. Avoid generating dust or aerosols. Do not eat, drink or smoke in work areas. After handling, wash hands thoroughly. Contaminated clothing should be removed and washed before reuse. Refer to the Safety Data Sheet (SDS) for complete safety information.

Application

6-Bromo-1,2,3,4-tetrahydro-2-quinolinone can serve as an organic synthesis intermediate and pharmaceutical intermediate, primarily used in laboratory research and development processes as well as chemical production processes.

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