6-Bromo-3-fluoro-2-nitrophenol: Properties & Lab FAQs

6-Bromo-3-fluoro-2-nitrophenol is a polyhalogenated aromatic phenol bearing bromo, fluoro, and nitro substituents that make it a versatile electrophilic building block for medicinal chemistry and materials science synthesis.

Chemical Name

6-Bromo-3-fluoro-2-nitrophenol

SKU / Catalog Number

B590443

Molecular Formula

C6H3BrFNO3

Molecular Weight

236.00 g/mol

Functional Groups

Phenol (–OH), Bromo (–Br), Fluoro (–F), Nitro (–NO2)

Primary Application

Electrophilic aromatic building block for cross-coupling, nucleophilic aromatic substitution, and heterocycle synthesis

What Is 6-Bromo-3-fluoro-2-nitrophenol and Why Is It Used?

6-Bromo-3-fluoro-2-nitrophenol (Aladdin SKU B590443) is a substituted phenol carrying three electron-withdrawing or halogen substituents on the aromatic ring: a bromine at position 6, a fluorine at position 3, and a nitro group at position 2, adjacent to the hydroxyl group. This combination of substituents strongly activates the ring toward nucleophilic aromatic substitution (SNAr), particularly at the positions bearing the halogen atoms. The nitro group ortho to the hydroxyl also lowers the pKa of the phenolic proton, increasing acidity relative to unsubstituted phenol.

In synthetic and medicinal chemistry, this compound serves as a multifunctional building block. The C–Br bond is amenable to palladium-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura, Buchwald-Hartwig), while the C–F bond can be displaced under SNAr conditions. The nitro group offers a handle for subsequent reduction to an amine, enabling further elaboration into benzimidazoles, benzoxazoles, or other privileged heterocyclic scaffolds.

How Should 6-Bromo-3-fluoro-2-nitrophenol Be Stored and Handled?

As with most polyhalogenated nitrophenols, 6-Bromo-3-fluoro-2-nitrophenol should be stored in a tightly sealed container away from light, moisture, and heat. A cool, dry environment (typically 2–8 °C or room temperature under desiccation, per the certificate of analysis) is recommended to prevent degradation of the nitro and halogen functionalities.

When handling this compound in the laboratory, appropriate personal protective equipment (PPE) must be used, including nitrile gloves, safety goggles, and a laboratory coat. All weighing and transfers should be performed in a well-ventilated fume hood. Nitroaromatic compounds may be irritating to skin and mucous membranes; inhalation of dust must be avoided. Researchers should consult the Safety Data Sheet (SDS) supplied with SKU B590443 before first use.

Waste disposal must comply with local regulations for halogenated organic compounds. Do not dispose of this material down the drain without appropriate treatment.

What Reactions Can 6-Bromo-3-fluoro-2-nitrophenol Undergo?

The compound's three reactive sites provide orthogonal handles for selective synthetic manipulation:

• C–Br bond: Undergoes palladium-catalyzed cross-coupling (Suzuki, Negishi, Buchwald-Hartwig amination), allowing introduction of aryl, heteroaryl, or amino groups.
• C–F bond: Activated toward nucleophilic aromatic substitution (SNAr) by the flanking nitro and other electron-withdrawing groups. Amines, alkoxides, and thiols can displace fluoride under mild to moderate conditions.
• Nitro group (–NO2): Reducible to a primary amine (–NH2) via catalytic hydrogenation or iron/acetic acid reduction, enabling cyclization to benzimidazoles, benzoxazoles, or anthranilic acid derivatives when combined with the adjacent phenol or newly introduced substituents.
• Phenolic –OH: Can be O-alkylated or O-acylated, or used as a directing group in metal-catalyzed reactions.

Researchers should verify compatibility of reaction conditions with all three substituents before proceeding, as selectivity may require careful choice of catalyst, solvent, and temperature.

Purity, Specification, and Quality Assurance

Aladdin Scientific supplies 6-Bromo-3-fluoro-2-nitrophenol (B590443) with a certificate of analysis (CoA) confirming lot-specific purity. Customers are encouraged to request the CoA for their specific lot prior to or at the time of purchase. Typical characterization data for this class of compound includes HPLC purity, NMR (1H, 13C, 19F), and mass spectrometric confirmation of molecular weight.

If your application requires a higher purity grade or custom quantity, please contact Aladdin Scientific's technical support or sales team. The internal reference code BD245507 may be used when communicating with customer service regarding this product.

All specifications listed on the product page supersede those in this document in the event of discrepancy. Always verify the current CoA before use in critical assays or regulatory studies.

Ordering and Availability

6-Bromo-3-fluoro-2-nitrophenol is available from Aladdin Scientific under SKU B590443. To place an order, visit the Aladdin Scientific website, search by SKU or product name, and proceed through the standard ordering workflow. Institutional purchase orders, credit card, and other approved payment methods are accepted.

For bulk quantities, custom packaging, or expedited shipping inquiries, contact the Aladdin Scientific sales team directly. Stock availability can vary; placing orders in advance is recommended for time-sensitive research projects. Shipping is conducted in accordance with applicable regulations for the transport of chemical reagents.

Frequently asked questions

What is the molecular formula and molecular weight of 6-Bromo-3-fluoro-2-nitrophenol?

The molecular formula of 6-Bromo-3-fluoro-2-nitrophenol is C6H3BrFNO3 and the molecular weight is approximately 236.00 g/mol. These values should be confirmed against the certificate of analysis for SKU B590443, as lot-specific data takes precedence.

Is 6-Bromo-3-fluoro-2-nitrophenol suitable for palladium-catalyzed cross-coupling reactions?

Yes. The C–Br bond in 6-Bromo-3-fluoro-2-nitrophenol is well-suited for palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig amination. Researchers should select appropriate ligands and base systems compatible with the acidic phenol and the electron-withdrawing nitro group present on the ring to achieve optimal yields.

Can the fluorine atom in 6-Bromo-3-fluoro-2-nitrophenol be selectively displaced?

Yes. The fluorine at position 3 is activated toward nucleophilic aromatic substitution (SNAr) due to the electron-withdrawing nitro group at position 2. Nucleophiles such as amines, sodium alkoxides, and thiols can selectively displace the fluoride under appropriate conditions, while leaving the C–Br bond intact for subsequent cross-coupling steps.

What safety precautions are required when handling 6-Bromo-3-fluoro-2-nitrophenol?

Researchers should wear appropriate PPE including nitrile gloves, safety goggles, and a lab coat when handling this compound. All operations should be performed in a fume hood to avoid inhalation of dust or vapors. The Safety Data Sheet (SDS) for SKU B590443 must be reviewed before first use, and waste must be disposed of in accordance with local regulations for halogenated organic compounds.

How do I request a certificate of analysis (CoA) for Aladdin SKU B590443?

You can request a lot-specific certificate of analysis for B590443 directly through the Aladdin Scientific website by entering your lot number on the product page, or by contacting Aladdin Scientific customer service. The internal reference code BD245507 can be used when communicating with customer service to identify this product.

References

1. Aladdin Scientific product page for 6-Bromo-3-fluoro-2-nitrophenol, SKU B590443, internal reference BD245507.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. Wiley, 1992. (General reference for SNAr and cross-coupling reactions involving halogenated aromatics.)

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