4-Bromo-2-fluoro-6-nitrotoluene: Properties & Lab Uses

4-Bromo-2-fluoro-6-nitrotoluene is a trisubstituted aromatic building block bearing bromo, fluoro, and nitro functional groups on a toluene scaffold, making it a versatile intermediate for medicinal chemistry, agrochemical synthesis, and materials research.

CAS Number

Refer to product datasheet (B589276)

Molecular Formula

C7H5BrFNO2

Molecular Weight

234.02 g/mol

Functional Groups

Bromo, Fluoro, Nitro, Methyl on benzene ring

Key Application

Synthetic intermediate in pharmaceutical and agrochemical research

Storage Condition

Store in a cool, dry, well-ventilated area away from incompatible materials; confirm with SDS

Chemical Identity and Structure

4-Bromo-2-fluoro-6-nitrotoluene (SKU: B589276) belongs to the class of polyhalogenated nitroaromatic compounds. Its molecular formula is C₇H₅BrFNO₂, with a molecular weight of approximately 234.02 g/mol. The compound features a toluene core bearing three distinct substituents: a bromine atom at the 4-position, a fluorine atom at the 2-position, and a nitro group at the 6-position, with the methyl group at the 1-position.

This substitution pattern creates a sterically and electronically differentiated aromatic ring. The electron-withdrawing nitro and fluoro groups deactivate the ring toward electrophilic aromatic substitution while activating it toward nucleophilic aromatic substitution (S_NAr), particularly at positions ortho and para to the nitro group. The C–F bond is orthogonal in reactivity to the C–Br bond, allowing chemists to exploit selective cross-coupling or displacement reactions at either halogen site.

Synthesis and Reactivity

Polysubstituted nitrotoluenes such as 4-Bromo-2-fluoro-6-nitrotoluene are typically prepared via directed nitration of pre-halogenated toluene derivatives or via halogenation of appropriately substituted nitrotoluene precursors. The presence of multiple directing groups must be carefully managed to achieve regioselectivity.

In downstream synthesis, this compound participates in several key reaction classes:

• Palladium-catalyzed cross-coupling: The C–Br bond is well-suited for Suzuki–Miyaura, Negishi, and Buchwald–Hartwig coupling reactions, enabling introduction of aryl, vinyl, or amino groups.
• Nucleophilic aromatic substitution (S_NAr): The activated C–F bond can be displaced by amines, alkoxides, or thiolates under appropriate conditions, providing access to diaryl ethers, anilines, and thioethers.
• Nitro group reduction: Reduction of the nitro group (e.g., via catalytic hydrogenation or iron/acetic acid) furnishes the corresponding aniline derivative, a versatile handle for further functionalization.

These orthogonal reactivities make 4-Bromo-2-fluoro-6-nitrotoluene a highly flexible three-way synthetic handle for constructing complex molecular architectures.

Research Applications

The multifunctional substitution pattern of 4-Bromo-2-fluoro-6-nitrotoluene positions it as a valuable intermediate across several research disciplines:

Medicinal Chemistry: Fluorine substitution on aromatic rings is a well-established strategy for improving metabolic stability, membrane permeability, and binding affinity of drug candidates. The nitro group can be reduced to an amine for incorporation into amide bonds, ureas, or sulfonamides—common pharmacophoric motifs. The reactive C–Br bond enables rapid diversification via palladium catalysis.

Agrochemical Research: Halogenated nitroaromatics serve as key intermediates in the synthesis of herbicides, fungicides, and insecticides. The structural motifs accessible from this compound overlap with known agrochemical pharmacophores.

Materials Science: Nitroaromatic and fluoroaromatic compounds are used in the preparation of functional dyes, liquid crystal components, and nonlinear optical materials. The electron-deficient aromatic core may serve as an acceptor unit in push–pull chromophore architectures.

Safety, Handling, and Storage

As with all nitroaromatic and halogenated compounds, appropriate precautions must be observed when handling 4-Bromo-2-fluoro-6-nitrotoluene. Researchers should consult the Safety Data Sheet (SDS) supplied with product B589276 before use. General guidelines include:

• Personal Protective Equipment (PPE): Wear appropriate gloves, safety goggles, and a lab coat. Work in a fume hood to minimize inhalation exposure.
• Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated location, away from strong reducing agents, bases, and ignition sources.
• Waste Disposal: Dispose of in accordance with local, regional, and national regulations for halogenated organic waste.
• First Aid: In case of skin or eye contact, rinse thoroughly with water and seek medical attention as indicated in the SDS.

Nitroaromatic compounds may present acute toxicity and environmental hazard concerns. All specific hazard classifications and first-aid measures are detailed in the product SDS.

Frequently asked questions

What makes 4-Bromo-2-fluoro-6-nitrotoluene useful as a synthetic intermediate?

The compound carries three orthogonally reactive functional handles—a C–Br bond for palladium-catalyzed cross-coupling, a C–F bond amenable to nucleophilic aromatic substitution, and a nitro group reducible to an amine—allowing chemists to build complex molecules through sequential, selective transformations.

How should I store 4-Bromo-2-fluoro-6-nitrotoluene in the laboratory?

Store the compound in a tightly sealed container under cool, dry, and well-ventilated conditions, away from strong reducing agents and ignition sources. Always refer to the product Safety Data Sheet (SDS) for specific storage requirements and hazard information.

Can the nitro group in 4-Bromo-2-fluoro-6-nitrotoluene be selectively reduced without affecting the halogen substituents?

Selective nitro reduction is generally achievable using mild conditions such as iron powder in acetic acid or transfer hydrogenation protocols, which can preserve C–Br and C–F bonds; however, conditions must be optimized for each specific substrate, and researchers should consult the primary literature for guidance.

What Aladdin Scientific product SKU corresponds to 4-Bromo-2-fluoro-6-nitrotoluene?

4-Bromo-2-fluoro-6-nitrotoluene is available from Aladdin Scientific under SKU B589276. Contact our technical support team for availability, pricing, and bulk inquiries.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for nucleophilic aromatic substitution and nitro reduction reactions.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Reference for aromatic substitution patterns and halogen reactivity.)
3. Aladdin Scientific. Product Datasheet: 4-Bromo-2-fluoro-6-nitrotoluene, SKU B589276. (BD219580)

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