2-Bromo-3-(difluoromethoxy)pyridine: Key Facts & FAQs
2-Bromo-3-(difluoromethoxy)pyridine: Key Facts & FAQs
2-Bromo-3-(difluoromethoxy)pyridine is a fluorinated heteroaromatic building block widely used in medicinal chemistry and pharmaceutical synthesis as a versatile electrophilic coupling partner.
- Chemical Name
- 2-Bromo-3-(difluoromethoxy)pyridine
- SKU / Product Code
- B734289
- Molecular Formula
- C6H4BrF2NO
- Molecular Weight
- 224.00 g/mol (calculated)
- Key Functional Groups
- Aryl bromide, difluoromethoxy (–OCHF2)
- Primary Application
- Pharmaceutical intermediate, cross-coupling reactions
- Supplier
- Aladdin Scientific
What Is 2-Bromo-3-(difluoromethoxy)pyridine?
2-Bromo-3-(difluoromethoxy)pyridine (SKU: B734289) is a halogenated, fluorine-containing pyridine derivative. Its structure features a pyridine ring bearing a bromine atom at the 2-position and a difluoromethoxy (–OCHF2) substituent at the 3-position. The difluoromethoxy group is a well-established bioisostere of hydroxyl and thiol groups in drug design, imparting improved metabolic stability, lipophilicity modulation, and membrane permeability to candidate molecules. The aryl bromide functionality renders this compound an excellent substrate for palladium-catalysed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings, making it a highly versatile synthetic building block.
Handling, Storage, and Safety
As with all organobromine and organofluorine reagents, appropriate precautions should be taken when handling 2-Bromo-3-(difluoromethoxy)pyridine. Users should consult the product-specific Safety Data Sheet (SDS) available from Aladdin Scientific prior to use. General guidance includes working in a well-ventilated fume hood, wearing appropriate personal protective equipment (nitrile gloves, safety glasses, and lab coat), and avoiding inhalation of vapours or skin contact. The compound should be stored in a tightly sealed container in a cool, dry, well-ventilated area, away from incompatible materials such as strong oxidisers and strong bases. Specific hazard classifications, GHS pictograms, and first-aid measures are detailed in the official SDS for SKU B734289.
Synthetic Applications and Reactivity
The bromine atom at the 2-position of the pyridine ring is activated by the ring nitrogen, making it particularly reactive in transition-metal-catalysed cross-coupling reactions. Common transformations include: (1) Suzuki–Miyaura coupling with aryl or heteroaryl boronic acids to access biaryl scaffolds; (2) Buchwald–Hartwig amination for the introduction of amine substituents; (3) Negishi coupling with organozinc reagents; and (4) lithium–halogen exchange at low temperature to generate the corresponding 2-lithiopyridine intermediate for further elaboration. The –OCHF2 group is generally stable under standard cross-coupling conditions, allowing selective functionalisation at the C–Br bond without affecting the fluorinated ether moiety.
Ordering, Specifications, and Purity
2-Bromo-3-(difluoromethoxy)pyridine is available from Aladdin Scientific under SKU B734289. For up-to-date information on available pack sizes, purity grade, certificate of analysis (CoA), and current pricing, please visit the product page on the Aladdin Scientific website or contact our customer service team. When placing an order, quoting the SKU ensures accurate fulfilment. Bulk quantities and custom specifications may be available upon request — please enquire via the Aladdin Scientific procurement or custom-synthesis channels.
Frequently Asked Questions Overview
The following FAQ section addresses the most common enquiries received from researchers and procurement personnel regarding 2-Bromo-3-(difluoromethoxy)pyridine (B734289), covering topics such as solubility, reactivity, storage conditions, and ordering logistics. If your question is not answered below, please contact Aladdin Scientific customer support directly for technical or commercial assistance.
Frequently asked questions
What is the recommended solvent for dissolving 2-Bromo-3-(difluoromethoxy)pyridine?
2-Bromo-3-(difluoromethoxy)pyridine is expected to be soluble in common organic solvents such as dichloromethane, tetrahydrofuran, dimethylformamide, and acetonitrile based on its structural characteristics as a lipophilic halogenated heterocycle. It is generally not recommended for use in neat water due to its hydrophobic character. Always verify solubility experimentally at your target concentration before use.
Is 2-Bromo-3-(difluoromethoxy)pyridine suitable for Suzuki–Miyaura cross-coupling reactions?
Yes. The aryl C–Br bond at the electron-deficient 2-position of the pyridine ring is well-suited for palladium-catalysed Suzuki–Miyaura coupling with aryl and heteroaryl boronic acids or boronate esters. Standard Pd(0) or Pd(II) precatalyst systems with appropriate phosphine ligands and base in mixed aqueous-organic solvent systems are typically effective. The –OCHF2 substituent is stable under typical coupling conditions.
What storage conditions are required for 2-Bromo-3-(difluoromethoxy)pyridine?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from heat sources, direct sunlight, strong oxidising agents, and strong bases. For precise storage temperature recommendations and shelf-life data, refer to the Certificate of Analysis and Safety Data Sheet provided with SKU B734289 from Aladdin Scientific.
How do I place an order for 2-Bromo-3-(difluoromethoxy)pyridine from Aladdin Scientific?
You can order 2-Bromo-3-(difluoromethoxy)pyridine directly through the Aladdin Scientific website using SKU B734289. Alternatively, contact our sales or customer service team by email or phone to request a quotation, discuss bulk pricing, or enquire about custom pack sizes. Quoting the SKU at the time of order ensures accurate and timely fulfilment.
What is the role of the difluoromethoxy group in drug discovery applications?
The difluoromethoxy (–OCHF2) group is a recognised bioisostere of hydroxyl (–OH) and thiol (–SH) groups in medicinal chemistry. Incorporation of –OCHF2 into drug candidates can improve metabolic stability by blocking oxidative metabolism at that site, modulate lipophilicity, and enhance membrane permeability, all of which can contribute to improved pharmacokinetic profiles. These properties make 2-Bromo-3-(difluoromethoxy)pyridine a valuable building block in lead optimisation campaigns.
References
- Aladdin Scientific Product Page: 2-Bromo-3-(difluoromethoxy)pyridine, SKU B734289.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press, 2012. (General reference for cross-coupling reactions and organolithium chemistry.)
- Müller, K.; Faeh, C.; Diederich, F. Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science 2007, 317, 1881–1886. doi:10.1126/science.1131943
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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