6-Bromo-4-methylquinolin-2-ol: Properties & Lab FAQ

6-Bromo-4-methylquinolin-2-ol is a brominated quinolinone heterocycle widely employed as a versatile synthetic building block in medicinal chemistry, agrochemical research, and the development of biologically active compounds.

CAS Number

Needs verification — not confirmed in source material

Molecular Formula

C10H8BrNO

Molecular Weight

Approximately 238.08 g/mol (needs review)

Product SKU

B187870

Compound Class

Brominated quinolin-2(1H)-one (quinolinol tautomer)

Primary Application

Synthetic building block for medicinal chemistry and heterocyclic synthesis

What Is 6-Bromo-4-methylquinolin-2-ol?

6-Bromo-4-methylquinolin-2-ol is a halogenated quinolinone derivative belonging to the broader family of quinoline heterocycles. In solid state and in many solvent systems, the compound predominantly exists in the quinolin-2(1H)-one tautomeric form rather than the 2-hydroxyquinoline form, a characteristic common to 2-hydroxyquinoline derivatives. The bromine substituent at the 6-position and the methyl group at the 4-position provide distinct handles for further functionalization via cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings. These features make the compound a valuable intermediate in the construction of more complex nitrogen-containing heterocyclic frameworks relevant to pharmaceutical and agrochemical discovery programs.

Solubility and Recommended Solvents

Like most quinolin-2-one derivatives, 6-Bromo-4-methylquinolin-2-ol has limited solubility in water due to its aromatic, lipophilic character. It is generally soluble in polar aprotic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF), and in halogenated solvents such as dichloromethane. Moderate solubility may be observed in ethanol and other lower alcohols, particularly with gentle warming. Researchers should prepare stock solutions in DMSO when biological assay compatibility is required, bearing in mind that DMSO concentration in final assay media should be kept below 0.1–1% to avoid cytotoxicity artifacts. Exact solubility data for this specific compound should be determined experimentally, as precise values are not confirmed in the current source material.

Storage, Stability and Handling Precautions

6-Bromo-4-methylquinolin-2-ol should be stored in a tightly sealed container, away from light, moisture, and incompatible materials such as strong oxidising agents and strong bases. Storage at room temperature in a cool, dry location is typical for solid quinolinone derivatives; however, refrigerated storage (2–8 °C) may be preferable for long-term preservation of purity. Always consult the product Safety Data Sheet (SDS) available from Aladdin Scientific before handling. Standard laboratory personal protective equipment (PPE) — including nitrile gloves, safety glasses, and a lab coat — should be worn. Work in a well-ventilated area or fume hood when weighing or handling the powder to avoid inhalation of fine particulates. Specific GHS hazard classifications for this compound should be verified against the current SDS.

Applications in Synthetic and Medicinal Chemistry

The quinolin-2-one scaffold is found in numerous pharmacologically relevant natural products and drug candidates, with documented activities spanning antibacterial, antifungal, antiviral, anticancer, and kinase-inhibitory properties across the broader literature. The 6-bromo substituent in 6-Bromo-4-methylquinolin-2-ol is particularly useful as a handle for palladium-catalysed cross-coupling reactions, enabling introduction of aryl, heteroaryl, vinyl, or alkynyl groups at this position to generate diverse analogue libraries. The 4-methyl group can also participate in further transformations, such as benzylic oxidation or halogenation. This combination of functional group handles makes SKU B187870 a practical and efficient starting point for medicinal chemists engaged in scaffold decoration and structure–activity relationship (SAR) studies.

Ordering, Specifications and Quality

6-Bromo-4-methylquinolin-2-ol is available from Aladdin Scientific under SKU B187870. Researchers and procurement teams are encouraged to visit the product page on the Aladdin Scientific website for up-to-date information on available pack sizes, purity grade, certificate of analysis (CoA), and current pricing. Aladdin Scientific provides CoA documentation with each lot, including purity data typically determined by HPLC or NMR, ensuring that researchers receive material meeting defined quality standards. For bulk inquiries, custom packaging, or questions about lead times, please contact Aladdin Scientific customer service directly. Returns and refunds are subject to Aladdin Scientific's standard returns policy; please refer to the help and customer service section of the website for full details.

Frequently asked questions

What is the tautomeric form of 6-Bromo-4-methylquinolin-2-ol in solution?

2-Hydroxyquinoline derivatives such as 6-Bromo-4-methylquinolin-2-ol exist in equilibrium between the 2-hydroxyquinoline and quinolin-2-one tautomers. In the solid state and in polar solvents, the lactam (quinolin-2-one) form is generally predominant. Researchers performing NMR characterisation should account for this tautomerism when interpreting spectra.

Which cross-coupling reactions are suitable for functionalising the bromine in 6-Bromo-4-methylquinolin-2-ol?

The C–Br bond at the 6-position is amenable to a range of palladium-catalysed cross-coupling reactions, including Suzuki–Miyaura (boronic acid coupling), Sonogashira (terminal alkyne coupling), and Buchwald–Hartwig (amination) reactions. Standard reaction conditions used for aryl bromides are generally applicable, though optimisation may be needed for this specific substrate due to the presence of the NH lactam functionality.

How should I store 6-Bromo-4-methylquinolin-2-ol to maintain its purity over time?

Store the compound in a tightly sealed container, protected from light and moisture, in a cool dry location. Refrigerated storage at 2–8 °C is recommended for long-term preservation. Always allow the container to equilibrate to room temperature before opening to prevent condensation from forming on the compound. Refer to the Aladdin Scientific SDS and CoA for lot-specific guidance.

What solvents can I use to prepare a stock solution of 6-Bromo-4-methylquinolin-2-ol for biological assays?

DMSO is generally the preferred solvent for preparing stock solutions intended for biological assays, as it offers good solvating power for lipophilic heterocycles and is compatible with most cell-based and biochemical assay formats. Ensure that the final DMSO concentration in the assay does not exceed 0.1–1% to minimise solvent-related cytotoxicity. Ethanol may serve as an alternative for certain applications.

How do I obtain a Certificate of Analysis (CoA) for my lot of B187870?

Certificates of Analysis for Aladdin Scientific products are available through the product page on the Aladdin Scientific website by entering your lot number. If you require assistance locating your CoA, please contact Aladdin Scientific customer service with your order number and lot number and the team will provide the documentation promptly.

References

1. General reference on quinolin-2-one tautomerism and synthetic utility — textbook-level knowledge; no specific citation confirmed in source material.
2. Palladium-catalysed cross-coupling reactions of aryl bromides — general synthetic chemistry knowledge; specific references for this substrate not confirmed.
3. Aladdin Scientific product page for B187870 (6-Bromo-4-methylquinolin-2-ol) — primary source for SKU, product name and availability.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.