4-Bromo-2-(trifluoromethyl)benzaldehyde: Key Facts & FAQs

4-Bromo-2-(trifluoromethyl)benzaldehyde is a halogenated, electron-deficient aromatic aldehyde widely used as a versatile synthetic building block in medicinal chemistry, agrochemical research, and materials science.

CAS Number

886498-68-6

Molecular Formula

C8H4BrF3O

Molecular Weight

253.02 g/mol

Appearance

White to off-white crystalline solid

Key Functional Groups

Aldehyde (–CHO), bromine substituent, trifluoromethyl (–CF3) group

Aladdin SKU

B120907

Chemical Identity and Structure

4-Bromo-2-(trifluoromethyl)benzaldehyde (CAS 886498-68-6) is an aromatic aldehyde bearing two electron-withdrawing substituents on the benzene ring: a bromine atom at the 4-position and a trifluoromethyl (–CF3) group at the 2-position, with the aldehyde functionality at the 1-position. The molecular formula is C8H4BrF3O with a molecular weight of approximately 253.02 g/mol.

The combined presence of the –CF3 and bromo groups renders the aromatic ring strongly electron-deficient, increasing the electrophilicity of the aldehyde carbonyl. The –CF3 group also imparts high lipophilicity, metabolic stability, and favorable membrane permeability to derived compounds, making this aldehyde particularly attractive for pharmaceutical and agrochemical lead optimization.

Synthetic Applications and Reactivity

4-Bromo-2-(trifluoromethyl)benzaldehyde serves as a multifunctional building block in organic synthesis, offering two independent handles for chemical elaboration: the reactive aldehyde group and the aryl bromide.

• Aldehyde reactivity: The aldehyde participates in condensation reactions (e.g., Knoevenagel, reductive amination, Wittig, and imine formation), providing access to diverse scaffolds including imines, amines, alcohols, and olefins.
• Aryl bromide cross-coupling: The C–Br bond is an excellent partner for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Heck, Sonogashira, and Buchwald–Hartwig amination, enabling introduction of diverse aryl, vinyl, alkynyl, or amino groups.
• Pharmaceutical and agrochemical synthesis: The trifluoromethyl group improves metabolic stability and bioavailability of derived drug candidates, making this aldehyde a valued intermediate in medicinal chemistry campaigns.

Handling, Storage, and Safety

As with all aromatic aldehydes and halogenated organic compounds, appropriate safety precautions should be observed when working with 4-Bromo-2-(trifluoromethyl)benzaldehyde.

• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area, away from direct sunlight and incompatible oxidizing agents. Refrigerated storage (2–8 °C) is recommended to maintain long-term stability.
• Handling: Use in a fume hood. Wear appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and a lab coat. Avoid inhalation of dust or vapors.
• Stability: The compound is stable under recommended storage conditions. Protect from moisture and prolonged exposure to light to prevent aldehyde oxidation or other degradation.
• Disposal: Dispose of in accordance with local regulations for halogenated organic waste.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Purity, Specification, and Quality

Aladdin Scientific supplies 4-Bromo-2-(trifluoromethyl)benzaldehyde (SKU: B120907) as a research-grade reagent. Typical quality parameters include:

• Purity: Confirmed by GC or HPLC analysis; researchers should consult the current Certificate of Analysis (CoA) for the specific lot being used.
• Characterization: Identity is confirmed by standard analytical techniques including NMR spectroscopy and mass spectrometry.
• Lot-specific CoA: A Certificate of Analysis with purity data and analytical results is available for each production lot upon request or via the Aladdin Scientific website.

For quality-critical applications such as GMP-adjacent synthesis or reference standard preparation, users should verify the CoA data and consider additional in-house purity testing.

Ordering and Availability

4-Bromo-2-(trifluoromethyl)benzaldehyde is available from Aladdin Scientific under SKU B120907. It is offered in multiple pack sizes to suit both exploratory research and larger-scale synthetic needs.

To order, visit the Aladdin Scientific website and search by product name or SKU number. Bulk or custom quantity inquiries can be directed to the Aladdin Scientific sales team. Standard shipping conditions apply; the compound should be shipped and stored at appropriate temperatures to maintain integrity.

For questions about pricing, lead times, or custom synthesis inquiries, please contact Aladdin Scientific customer service directly.

Frequently asked questions

What is 4-Bromo-2-(trifluoromethyl)benzaldehyde used for in research?

It is primarily used as a multifunctional synthetic building block. The aldehyde group enables condensation and reductive amination reactions, while the aryl bromide enables palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura and Buchwald–Hartwig coupling. The trifluoromethyl group makes derived compounds attractive as pharmaceutical and agrochemical intermediates due to improved metabolic stability and lipophilicity.

How should 4-Bromo-2-(trifluoromethyl)benzaldehyde be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area away from direct sunlight. Refrigerated storage at 2–8 °C is recommended for long-term preservation. Protecting the material from moisture and prolonged light exposure will prevent aldehyde oxidation and other degradation pathways.

What is the Aladdin Scientific SKU for 4-Bromo-2-(trifluoromethyl)benzaldehyde?

The product is listed under SKU B120907 on the Aladdin Scientific platform. You can search by this number or by the full IUPAC name or CAS number 886498-68-6 on the website to locate the product and access the current Certificate of Analysis.

Can the aryl bromide in 4-Bromo-2-(trifluoromethyl)benzaldehyde be used in palladium-catalyzed cross-coupling reactions?

Yes. The C–Br bond is well-suited for a range of palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids), Heck (with alkenes), Sonogashira (with terminal alkynes), and Buchwald–Hartwig amination (with amines). The electron-withdrawing trifluoromethyl and aldehyde groups activate the ring toward oxidative addition, generally facilitating these reactions.

What safety precautions are needed when handling 4-Bromo-2-(trifluoromethyl)benzaldehyde?

Handle this compound in a fume hood wearing appropriate PPE including chemical-resistant gloves, safety goggles, and a lab coat. Avoid inhalation of dust or vapors. Dispose of waste according to local regulations for halogenated organic compounds. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

References

1. Aladdin Scientific product page for 4-Bromo-2-(trifluoromethyl)benzaldehyde, SKU B120907.
2. General reference: Fluorine in Medicinal Chemistry and Chemical Biology (Ed. Ojima, I.), Wiley-Blackwell, 2009 — role of –CF3 in drug design.
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007

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