4-Bromo-5-fluoro-2-methylpyridine: Properties & Uses

4-Bromo-5-fluoro-2-methylpyridine is a halogenated pyridine building block bearing both bromo and fluoro substituents alongside a methyl group, making it a versatile intermediate for pharmaceutical and agrochemical synthesis.

Chemical Name

4-Bromo-5-fluoro-2-methylpyridine

SKU

B190115

Molecular Formula

C6H5BrFN

Molecular Weight

190.01 g/mol

CAS Number

Needs review — not confirmed in source material

Compound Class

Halogenated heteroaromatic / pyridine derivative

Overview and Structural Features

4-Bromo-5-fluoro-2-methylpyridine (Aladdin SKU B190115) is a trisubstituted pyridine derivative in which bromine occupies the 4-position, fluorine occupies the 5-position, and a methyl group occupies the 2-position of the pyridine ring. This combination of substituents imparts distinct electronic and steric properties: the electron-withdrawing fluorine and the ring nitrogen together activate the carbon bearing bromine toward metal-catalyzed cross-coupling reactions, while the 2-methyl group can influence conformation and lipophilicity in downstream drug candidates.

The presence of both a reactive C–Br bond and a stable C–F bond in the same molecule makes this compound particularly attractive as a bifunctional building block, allowing sequential functionalization strategies in multi-step synthesis.

Synthetic Applications

The C–Br bond in 4-Bromo-5-fluoro-2-methylpyridine is well-suited for a range of palladium- and nickel-catalyzed cross-coupling reactions, including Suzuki–Miyaura (boronic acid coupling), Negishi (organozinc), Buchwald–Hartwig (C–N bond formation), and Sonogashira (terminal alkyne) couplings. These transformations allow researchers to introduce aryl, heteroaryl, amino, or alkynyl groups at the 4-position while preserving the C–F bond for further manipulation or as a metabolic-stability-enhancing element in drug design.

The 2-methyl group can also be exploited synthetically; under appropriate conditions it may be oxidized to a carboxylic acid or aldehyde, or used as a handle for benzylic functionalization, broadening the scope of accessible analogs.

Handling, Storage, and Safety

As with most halogenated heteroaromatic intermediates, 4-Bromo-5-fluoro-2-methylpyridine should be handled with standard laboratory precautions. Work in a well-ventilated fume hood, wear appropriate personal protective equipment (nitrile gloves, safety goggles, lab coat), and avoid inhalation of dust or vapors. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for comprehensive hazard, first-aid, and disposal information before use.

For storage, the compound should be kept in a tightly sealed container in a cool, dry environment away from strong oxidizers and strong bases. Typical storage conditions for solid halopyridines are at room temperature or slightly below (2–8 °C) to maintain long-term stability, though specific recommendations should be confirmed on the product label and SDS.

Purity, Specification, and Quality

Aladdin Scientific supplies 4-Bromo-5-fluoro-2-methylpyridine (SKU B190115) as a research-grade reagent. Purity and analytical data (e.g., GC purity, HPLC purity, NMR confirmation) are available on the product Certificate of Analysis (CoA), which can be requested from Aladdin's technical support team or downloaded from the product page. Researchers requiring custom purity levels, larger quantities, or specific packaging should contact Aladdin's sales team directly.

Frequently Asked Questions at a Glance

This section provides quick-reference answers to the most common technical and ordering questions received by Aladdin Scientific regarding 4-Bromo-5-fluoro-2-methylpyridine. Detailed answers are provided in the FAQ section below. For questions not addressed here, please contact Aladdin Scientific customer support.

Frequently asked questions

What cross-coupling reactions are suitable for 4-Bromo-5-fluoro-2-methylpyridine?

The C–Br bond makes this compound compatible with palladium-catalyzed Suzuki–Miyaura, Negishi, Sonogashira, and Buchwald–Hartwig cross-coupling reactions, enabling introduction of aryl, heteroaryl, alkynyl, and amino groups at the 4-position. The C–F bond at the 5-position is generally inert under standard cross-coupling conditions, allowing selective functionalization at the bromide site. Standard Pd catalysts such as Pd(PPh3)4 or Pd(dppf)Cl2 are typically employed.

How should 4-Bromo-5-fluoro-2-methylpyridine be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry location away from moisture, strong oxidizers, and strong bases. Many researchers store halopyridine building blocks at room temperature or at 2–8 °C for extended shelf life. Always refer to the Aladdin product label and the SDS for the most current, product-specific storage guidance.

What is the molecular formula and molecular weight of 4-Bromo-5-fluoro-2-methylpyridine?

4-Bromo-5-fluoro-2-methylpyridine has the molecular formula C6H5BrFN and a molecular weight of approximately 190.01 g/mol. These values are derived from its structural composition: a pyridine ring substituted with bromine (MW contribution ~79), fluorine (MW contribution ~19), and a methyl group, plus the ring nitrogen and five ring/methyl carbons with associated hydrogens.

Can the 2-methyl group of this compound be further functionalized?

Yes, the 2-methyl group can serve as a synthetic handle. It can be oxidized to a carboxylic acid or aldehyde using appropriate oxidants, or undergo benzylic bromination (e.g., with NBS under radical conditions) to afford a bromomethyl intermediate amenable to further substitution. The feasibility of such transformations should be validated experimentally in the context of the specific synthetic sequence employed.

How do I obtain a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) for SKU B190115?

The Certificate of Analysis and Safety Data Sheet for 4-Bromo-5-fluoro-2-methylpyridine (SKU B190115) can be downloaded from the product page on the Aladdin Scientific website or requested directly from Aladdin's customer support team. When contacting support, please provide the SKU (B190115) and, where applicable, the lot number from your product label for the most accurate documentation.

References

1. Aladdin Scientific product page for 4-Bromo-5-fluoro-2-methylpyridine, SKU B190115.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General cross-coupling methodology reference.)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level reference for haloarene reactivity and pyridine chemistry.)

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