4-Bromo-8-(trifluoromethoxy)quinoline: Properties & Uses
4-Bromo-8-(trifluoromethoxy)quinoline: Properties & Uses
4-Bromo-8-(trifluoromethoxy)quinoline is a fluorinated, halogenated quinoline building block widely employed in medicinal chemistry and pharmaceutical research as a versatile electrophilic intermediate for cross-coupling and nucleophilic substitution reactions.
- CAS / SKU
- SKU B732558; CAS number to be confirmed from certificate of analysis
- Molecular Formula
- C10H5BrF3NO
- Key Functional Groups
- C-4 bromo substituent (electrophilic handle for cross-coupling); C-8 trifluoromethoxy group (strong electron-withdrawing, metabolically stable)
- Primary Application
- Synthetic intermediate in medicinal chemistry, drug discovery, and agrochemical research
- Storage Recommendation
- Store in a cool, dry, well-ventilated area away from moisture and incompatible materials; specific conditions to be confirmed on SDS
- Supplier SKU
- B732558 (Aladdin Scientific)
What Is 4-Bromo-8-(trifluoromethoxy)quinoline?
4-Bromo-8-(trifluoromethoxy)quinoline is a halogenated, fluorine-containing quinoline heterocycle. The quinoline core is a bicyclic aromatic system consisting of a benzene ring fused to a pyridine ring, and it is a privileged scaffold in medicinal chemistry due to its presence in numerous bioactive molecules and approved drugs.
Two key substituents define this compound's reactivity profile. The bromine atom at the 4-position serves as an electrophilic handle ideally suited for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings, enabling rapid diversification of the scaffold. The trifluoromethoxy (–OCF₃) group at the 8-position is a strongly electron-withdrawing moiety that modulates the electronic density of the ring, enhances lipophilicity (as measured by increased logP), and confers excellent metabolic stability—properties highly desirable in drug candidates.
Note: Molecular weight and exact CAS number should be verified against the current certificate of analysis provided with SKU B732558.
What Are the Main Applications of This Compound?
4-Bromo-8-(trifluoromethoxy)quinoline is primarily used as a synthetic building block in the following research areas:
- Medicinal Chemistry & Drug Discovery: The compound serves as a versatile intermediate for constructing quinoline-based pharmacophores. Researchers use it to introduce the –OCF₃ group and the quinoline nitrogen into candidate molecules, targeting receptors, kinases, and other enzymes where fluorinated quinolines have demonstrated biological activity.
- Cross-Coupling Chemistry: The C–Br bond at position 4 is highly reactive toward Pd(0)/Pd(II)-catalyzed coupling protocols, making this reagent valuable for building biaryl, heteroaryl, and aminoquinoline libraries.
- Agrochemical Research: Fluorinated heterocycles are well-established in crop-protection compound design, and this scaffold may serve as an intermediate in the synthesis of candidate agrochemicals.
- Materials Science: Quinoline derivatives with electron-withdrawing substituents are occasionally explored in organic electronics applications, though this is a secondary application area.
Specific literature citations for biological activity data should be verified independently; review flag raised.
How Should This Compound Be Handled and Stored Safely?
As with all halogenated and fluorinated organic reagents, appropriate laboratory safety practices are essential when working with 4-Bromo-8-(trifluoromethoxy)quinoline:
- Personal Protective Equipment (PPE): Wear chemical-resistant gloves, laboratory coat, and eye protection at all times. Work in a well-ventilated fume hood.
- Storage: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, strong oxidizers, and strong bases. Specific temperature requirements should be confirmed on the Safety Data Sheet (SDS) for SKU B732558.
- Disposal: Dispose of waste in accordance with local, regional, and national regulations governing halogenated organic compounds.
- Spill Management: In the event of a spill, use appropriate absorbent material and dispose of as hazardous chemical waste. Avoid inhalation of dust or vapors.
Always consult the current SDS provided by Aladdin Scientific for SKU B732558 before use. SDS content supersedes general guidance given here.
How to Order and What to Expect from Aladdin Scientific
4-Bromo-8-(trifluoromethoxy)quinoline is available from Aladdin Scientific under SKU B732558. To place an order or obtain a quotation:
- Visit the Aladdin Scientific website and search for SKU B732558 or the full product name.
- Select the required pack size and quantity, then proceed through the standard checkout process.
- For bulk orders, institutional accounts, or custom packaging inquiries, contact the Aladdin Scientific sales team directly.
Upon receipt, customers should inspect the package for integrity, verify the lot number and certificate of analysis (CoA), and confirm purity data before use in critical experiments. The CoA will include confirmed CAS number, purity (typically assessed by GC or HPLC), and appearance data.
For questions about pricing, promotions, shipping conditions, or returns, refer to the respective policy pages on the Aladdin Scientific website or contact customer service.
Frequently asked questions
What cross-coupling reactions is 4-Bromo-8-(trifluoromethoxy)quinoline suitable for?
The C–Br bond at the 4-position makes this compound an excellent substrate for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids/esters), Buchwald–Hartwig (for C–N bond formation with amines), Sonogashira (with terminal alkynes), and Negishi couplings. These reactions enable efficient diversification of the quinoline scaffold for medicinal chemistry libraries.
Why is the trifluoromethoxy group important in drug discovery applications?
The –OCF₃ group is a strongly electron-withdrawing substituent that increases the lipophilicity of molecules (raising logP), which can improve membrane permeability and oral bioavailability. It also imparts exceptional metabolic stability because the C–O–CF₃ linkage is resistant to oxidative metabolism by cytochrome P450 enzymes. These properties make it a highly attractive bioisostere and pharmacokinetic-modulating group in modern drug design.
What solvents are recommended for dissolving 4-Bromo-8-(trifluoromethoxy)quinoline?
Based on the general physicochemical properties of halogenated, lipophilic quinoline derivatives, common organic solvents such as dichloromethane (DCM), tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and acetonitrile are expected to dissolve this compound effectively. Aqueous solubility is likely low due to the lipophilic –OCF₃ substituent. Solubility should be experimentally confirmed for each application; consult the CoA or contact Aladdin Scientific technical support for verified solubility data.
Is 4-Bromo-8-(trifluoromethoxy)quinoline available in custom quantities or bulk?
Aladdin Scientific offers this compound under SKU B732558 in standard pack sizes listed on the product page. For bulk quantities, custom packaging, or special purity grades, customers should contact the Aladdin Scientific sales team directly to discuss availability, lead times, and pricing. Institutional and corporate accounts may be eligible for volume discounts.
What purity grade can I expect, and how is it tested?
The purity of 4-Bromo-8-(trifluoromethoxy)quinoline (B732558) is reported on the certificate of analysis (CoA) accompanying each lot. Purity is typically assessed by gas chromatography (GC) or high-performance liquid chromatography (HPLC). Customers are advised to review the CoA for their specific lot upon receipt to confirm that the material meets their experimental requirements. For purity specifications, visit the product page or contact Aladdin Scientific customer service.
References
- Aladdin Scientific product page for 4-Bromo-8-(trifluoromethoxy)quinoline, SKU B732558. Retrieved from Aladdin Scientific official website.
- General reference: Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Wiley-VCH, 2004. (Background on trifluoromethoxy group properties in medicinal chemistry.)
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed. Wiley-Blackwell, 2010. (Background on quinoline chemistry and cross-coupling reactivity.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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