2-Bromo-3-(difluoromethoxy)pyridine: Properties & Uses

2-Bromo-3-(difluoromethoxy)pyridine is a halogenated, fluorine-containing heteroaromatic building block widely used as a synthetic intermediate in medicinal chemistry and agrochemical research.

Chemical Name

2-Bromo-3-(difluoromethoxy)pyridine

SKU

B734289

Molecular Formula

C6H4BrF2NO

Functional Groups

Aryl bromide, difluoromethoxy (OCHF2)

Primary Application

Synthetic intermediate for pharmaceutical and agrochemical building blocks

Storage Condition

Store in a cool, dry, well-ventilated area away from incompatible materials

What Is 2-Bromo-3-(difluoromethoxy)pyridine?

2-Bromo-3-(difluoromethoxy)pyridine (SKU: B734289) is a halogenated pyridine derivative bearing a difluoromethoxy (–OCHF₂) substituent at the 3-position and a bromine atom at the 2-position of the pyridine ring. The combination of an electrophilic aryl bromide and a metabolically stable difluoromethoxy group makes this compound a versatile building block in modern synthetic chemistry. The difluoromethoxy group is a bioisostere of hydroxyl and methoxy groups and is frequently introduced into drug candidates to improve metabolic stability, lipophilicity, and membrane permeability.

Key Chemical Properties and Structure

The molecular formula of 2-Bromo-3-(difluoromethoxy)pyridine is C₆H₄BrF₂NO. The compound features a six-membered heteroaromatic ring containing one nitrogen atom. The aryl C–Br bond at the 2-position is amenable to a wide range of transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and Miyaura borylation reactions. The –OCHF₂ group at the 3-position is electron-withdrawing and contributes to the overall electron-deficient character of the ring, which can influence regioselectivity in subsequent functionalization steps. The compound is expected to be a liquid or low-melting solid at ambient temperature, though exact physical constants should be confirmed from the certificate of analysis.

Applications in Medicinal Chemistry and Synthesis

2-Bromo-3-(difluoromethoxy)pyridine serves as a key intermediate in the preparation of pharmaceutically relevant molecules and agrochemicals. Researchers commonly use it in:

• Cross-coupling reactions: The C–Br handle allows efficient Pd- or Ni-catalyzed coupling with boronic acids, organozinc reagents, amines, and other nucleophiles to build complex heterocyclic scaffolds.
• Drug discovery: The difluoromethoxy-substituted pyridine core appears in bioactive molecules targeting enzymes and receptors; the –OCHF₂ group modulates pK_a, log P, and hydrogen-bond donor capacity relative to unsubstituted analogues.
• Agrochemical intermediates: Fluorinated pyridine derivatives are broadly used in the synthesis of fungicides, herbicides, and insecticides.

Because both the bromine and the difluoromethoxy group are pre-installed, use of this building block reduces synthetic steps compared with late-stage introduction of these functionalities.

Handling, Safety, and Storage

As with most organobromine and organofluorine compounds, appropriate laboratory safety precautions should be observed when handling 2-Bromo-3-(difluoromethoxy)pyridine:

• Use personal protective equipment (PPE) including nitrile gloves, safety glasses, and a lab coat.
• Handle in a well-ventilated fume hood to avoid inhalation of vapors.
• Store in a tightly sealed container in a cool, dry, well-ventilated area, away from strong bases and oxidizing agents.
• Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for detailed hazard classifications, first-aid measures, and disposal procedures before use.

Exact GHS hazard classifications and pictograms for this specific compound should be verified from the current SDS.

Ordering and Availability

2-Bromo-3-(difluoromethoxy)pyridine is available from Aladdin Scientific under SKU B734289. To place an order or request a quotation, contact your local Aladdin Scientific representative or visit the product page on the Aladdin Scientific website. For bulk quantities, custom packaging, or specific purity requirements, please reach out to our technical sales team. Certificates of Analysis (CoA) and Safety Data Sheets (SDS) are available upon request or via the product page.

Frequently asked questions

What reactions can 2-Bromo-3-(difluoromethoxy)pyridine be used in?

The aryl bromide functionality makes this compound suitable for a broad range of transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids), Buchwald–Hartwig (with amines), Negishi (with organozinc), and Miyaura borylation reactions. These transformations allow rapid construction of diversely functionalized pyridine scaffolds for drug discovery and materials science.

Why is the difluoromethoxy group important in drug design?

The difluoromethoxy (–OCHF2) group is a well-established bioisostere of hydroxyl and methoxy groups that improves the metabolic stability of drug candidates by resisting oxidative metabolism. It also modulates lipophilicity (log P) and can act as a weak hydrogen-bond donor through its C–H, which influences binding affinity to biological targets. These properties make –OCHF2-substituted heterocycles highly sought-after in medicinal chemistry programs.

How should 2-Bromo-3-(difluoromethoxy)pyridine be stored to maintain its integrity?

The compound should be stored in a tightly sealed container under cool, dry, and well-ventilated conditions, away from moisture, strong oxidizers, and strong bases. Always refer to the current Safety Data Sheet (SDS) from Aladdin Scientific for authoritative storage and handling guidance specific to this product.

What is the molecular formula and key structural features of this compound?

2-Bromo-3-(difluoromethoxy)pyridine has the molecular formula C6H4BrF2NO. It consists of a pyridine ring with a bromine substituent at the 2-position and a –OCHF2 group at the 3-position, combining an electrophilic aryl halide handle with an electron-withdrawing, metabolically stable fluorinated ether moiety.

Is a Certificate of Analysis (CoA) available for SKU B734289?

Yes, a Certificate of Analysis (CoA) for 2-Bromo-3-(difluoromethoxy)pyridine (SKU B734289) is available from Aladdin Scientific. You can request it through the product page on the Aladdin Scientific website or by contacting customer service with your lot number.

References

1. Hagmann, W. K. The Many Roles for Fluorine in Medicinal Chemistry. Journal of Medicinal Chemistry, 2008, 51(15), 4359–4369. doi:10.1021/jm800219f
2. Meanwell, N. A. Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design. Journal of Medicinal Chemistry, 2011, 54(8), 2529–2591. doi:10.1021/jm1013693
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. doi:10.1021/cr00039a007

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