2-Bromo-6-Fluoronaphthalene: Properties, Synthesis & Applications

2-Bromo-6-fluoronaphthalene is a difunctionalized naphthalene building block bearing both a carbon–bromine and a carbon–fluorine bond, enabling orthogonal reactivity that makes it a highly valuable intermediate in pharmaceutical, materials, and fine-chemical synthesis.

CAS Number

201849-14-1

Molecular Formula

C₁₀H₆BrF

Molecular Weight

225.06 g/mol

Key Functional Groups

Aryl bromide (C-Br) and aryl fluoride (C-F) at the 2- and 6-positions of the naphthalene ring

Primary Use

Intermediate in palladium-catalyzed cross-coupling reactions (Suzuki, Negishi, Buchwald–Hartwig) and directed metalation

Physical State

Solid at room temperature

SKU

B152882

Chemical Identity and Physical Properties

2-Bromo-6-fluoronaphthalene (CAS 201849-14-1) is a dihalogenated polycyclic aromatic hydrocarbon with the molecular formula C₁₀H₆BrF and a molecular weight of approximately 225.06 g/mol. The compound features a naphthalene scaffold substituted with a bromine atom at the 2-position and a fluorine atom at the 6-position, placing the two halogens on opposite rings of the bicyclic system in a geometry that minimizes steric interaction and maximizes synthetic versatility.

At room temperature the compound exists as a crystalline solid. Like other halogenated naphthalenes it exhibits low water solubility and is typically handled dissolved in common organic solvents such as tetrahydrofuran, dichloromethane, dimethylformamide, or toluene. Researchers should consult the product Safety Data Sheet (SDS) for specific handling, storage, and disposal requirements before use.

Reactivity and Synthetic Utility

The key synthetic appeal of 2-bromo-6-fluoronaphthalene lies in the orthogonal reactivity of its two carbon–halogen bonds. The C–Br bond is considerably more reactive than the C–F bond toward oxidative addition into palladium(0) and other transition-metal catalysts, allowing selective functionalization at the bromine-bearing carbon under standard cross-coupling conditions.

Palladium-catalyzed cross-coupling: The aryl bromide site participates readily in Suzuki–Miyaura (with aryl- or alkenylboronic acids/esters), Negishi (with organozinc reagents), Kumada (with Grignard reagents), and Sonogashira (with terminal alkynes) couplings. These reactions enable the rapid elaboration of the naphthalene core into biaryl, styrene, or alkynyl-naphthalene motifs commonly found in pharmaceuticals and organic electronic materials.

Buchwald–Hartwig amination: The C–Br bond can also engage in palladium-catalyzed C–N bond formation, providing access to aminonaphthalene derivatives that are useful as ligands or pharmacophores.

Directed metalation and SNAr: The electron-withdrawing fluorine atom activates the adjacent ring positions toward nucleophilic aromatic substitution (SNAr) and can also direct ortho-lithiation under cryogenic conditions, offering an additional handle for further functionalization once the bromine has been used in a coupling step.

Sequential functionalization: Because the C–Br and C–F bonds react under different conditions, chemists can perform two distinct transformations on a single substrate in a defined sequence, significantly streamlining the synthesis of complex, asymmetrically substituted naphthalene derivatives.

Applications in Pharmaceutical and Materials Research

Medicinal chemistry: Fluorinated naphthalene fragments are prevalent in drug discovery programs because fluorine substitution can improve metabolic stability, membrane permeability, and binding affinity through steric and electronic effects. 2-Bromo-6-fluoronaphthalene serves as a convenient entry point to fluoronaphthalene-containing drug candidates, allowing medicinal chemists to install diverse substituents at the 2-position via cross-coupling while retaining the fluorine pharmacophoric element at the 6-position.

Organic electronics and liquid crystals: Substituted naphthalenes are core structural units in organic semiconductors, fluorescent emitters, and liquid-crystal mesogens. The precise regiochemistry of 2-bromo-6-fluoronaphthalene makes it attractive for constructing extended π-conjugated systems and anisotropic materials, where the fluorine substituent can tune electronic properties and intermolecular packing interactions.

Agrochemical intermediates: Halogenated naphthalene derivatives have also found use as intermediates in the synthesis of fungicides and herbicides, broadening the relevance of this building block beyond the pharmaceutical sector.

Handling, Storage, and Safety Considerations

As with most halogenated aromatic compounds, 2-bromo-6-fluoronaphthalene should be handled with appropriate personal protective equipment, including chemical-resistant gloves, safety glasses, and a laboratory coat. Operations that may generate dust or aerosols should be performed in a well-ventilated fume hood.

For long-term storage, the compound should be kept in a tightly sealed container, protected from moisture and light, and stored at the temperature recommended on the product label or SDS. Improper storage conditions may lead to degradation or discoloration over time. Always consult the current Aladdin Scientific SDS for authoritative hazard classification, first-aid measures, and waste disposal procedures specific to this product (SKU B152882).

Researchers should follow all applicable institutional and regulatory requirements for the use and disposal of halogenated organic chemicals in their jurisdiction.

Why Choose Aladdin Scientific B152882

Aladdin Scientific supplies 2-bromo-6-fluoronaphthalene (SKU B152882) as a research-grade reagent intended to meet the purity and consistency demands of modern synthetic chemistry workflows. Each lot is subject to quality-control analysis to verify identity and purity, helping researchers minimize batch-to-batch variability and focus effort on their science rather than reagent qualification.

For specific purity certificates, analytical data (NMR, GC, HPLC), pricing, and available pack sizes, please visit the product page on the Aladdin Scientific website or contact our technical support team. Bulk quantities and custom specifications may be available upon request.

Frequently asked questions

What is the CAS number for 2-bromo-6-fluoronaphthalene?

The CAS registry number for 2-bromo-6-fluoronaphthalene is 201849-14-1. Aladdin Scientific lists this compound under SKU B152882.

Can 2-bromo-6-fluoronaphthalene be used in Suzuki–Miyaura cross-coupling reactions?

Yes. The aryl C–Br bond in 2-bromo-6-fluoronaphthalene is well-suited for palladium-catalyzed Suzuki–Miyaura coupling with boronic acids and boronic esters under standard conditions. The C–F bond remains intact under these conditions, providing a handle for subsequent functionalization if desired.

What makes the 2,6-substitution pattern on the naphthalene ring synthetically useful?

The 2- and 6-positions are located on opposite rings of the naphthalene scaffold, providing a well-separated, geometrically defined arrangement of the two halogens. This regiochemistry allows chemists to exploit the differential reactivity of C–Br versus C–F in sequential transformations, constructing asymmetrically functionalized naphthalene derivatives in a controlled and efficient manner.

How should 2-bromo-6-fluoronaphthalene be stored?

The compound should be stored in a tightly sealed container, away from moisture, light, and heat, at the temperature specified on the Aladdin Scientific product label or Safety Data Sheet. Refer to the current SDS for full storage and handling guidance.

Is 2-bromo-6-fluoronaphthalene relevant to pharmaceutical intermediate synthesis?

Yes. Fluorine-substituted naphthalene motifs are commonly incorporated into drug candidates to modulate metabolic stability, lipophilicity, and target binding. 2-Bromo-6-fluoronaphthalene provides a reactive handle (the C–Br bond) for rapid diversification of the fluoronaphthalene core, making it a useful building block in medicinal chemistry campaigns.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for cross-coupling reactions and aromatic halide reactivity.)
2. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. doi:10.1002/anie.201107017
3. Hagmann, W. K. The Many Roles for Fluorine in Medicinal Chemistry. J. Med. Chem. 2008, 51, 4359–4369. doi:10.1021/jm800219f

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