6-Bromothiazolo[5,4-b]pyridine: Properties, Uses & FAQs

6-Bromothiazolo[5,4-b]pyridine is a halogenated bicyclic heteroaromatic compound widely used as a versatile building block in medicinal chemistry and drug discovery research.

Chemical Name

6-Bromothiazolo[5,4-b]pyridine

SKU

B187737

Molecular Formula

C6H3BrN2S

Compound Class

Halogenated bicyclic heteroaromatic

Primary Application

Synthetic intermediate and building block in medicinal chemistry

Key Reactive Site

C–Br bond amenable to cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig)

What Is 6-Bromothiazolo[5,4-b]pyridine?

6-Bromothiazolo[5,4-b]pyridine (SKU: B187737) is a fused bicyclic heteroaromatic compound consisting of a thiazole ring fused to a pyridine ring at the [5,4-b] positions, with a bromine substituent at the 6-position. The molecular formula is C₆H₃BrN₂S. This scaffold combines the electron-deficient character of both the pyridine and thiazole rings, conferring significant π-electron-deficient aromatic character. This property makes it highly attractive as a pharmacophore or as a core scaffold in the design of bioactive molecules targeting diverse biological pathways.

The presence of sulfur and two nitrogen atoms within the fused ring system provides multiple sites for non-covalent interactions (hydrogen bonding, π–π stacking, and coordination chemistry), which are frequently exploited in drug–target binding. The compound is supplied by Aladdin Scientific to support research in heterocyclic chemistry, pharmaceutical development, and materials science.

Chemical Properties and Structural Features

The thiazolo[5,4-b]pyridine core is a planar, aromatic bicyclic system. Fusion of the thiazole and pyridine rings produces a highly conjugated, electron-poor framework that is metabolically stable compared to many monocyclic heterocycles. Key structural features include:

• Bromine at C-6: The aryl bromide is the primary handle for chemical elaboration. It participates readily in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, Sonogashira, and Buchwald–Hartwig couplings, enabling rapid diversification of the scaffold.
• Ring nitrogen atoms: The pyridine-type nitrogen and the imine-type nitrogen of the thiazole ring contribute to the compound's hydrogen-bond accepting capability and can coordinate metal catalysts during reactions.
• Sulfur atom: Contributes to the polarizability of the ring system and can participate in weak non-covalent interactions with biological targets.

These combined features make 6-Bromothiazolo[5,4-b]pyridine a privileged heterocyclic scaffold in synthetic and medicinal chemistry.

Applications in Medicinal Chemistry and Synthesis

6-Bromothiazolo[5,4-b]pyridine serves primarily as a synthetic building block and intermediate. Its main applications include:

• Drug discovery: The thiazolopyridine scaffold appears in compounds with reported kinase inhibitory, antimicrobial, and anti-inflammatory activities. Researchers use this brominated derivative to introduce the bicyclic core into drug candidates via cross-coupling chemistry.
• Fragment-based drug design (FBDD): The compact, rigid, and electron-deficient ring system is an attractive fragment for screening against therapeutic targets.
• Cross-coupling chemistry: The C–Br bond undergoes Suzuki–Miyaura coupling with aryl- and heteroarylboronic acids, Buchwald–Hartwig amination to install amine functionality, and other Pd(0)/Pd(II)-catalyzed transformations to construct complex heterocyclic architectures.
• Materials science: Electron-deficient heteroaromatic frameworks are explored as components of organic semiconductors and coordination polymers.

Researchers seeking to diversify chemical libraries around the thiazolopyridine pharmacophore will find this compound an efficient and reliable starting material.

Handling, Storage, and Safety Guidance

As with most halogenated heteroaromatic compounds, appropriate laboratory safety practices should be observed when handling 6-Bromothiazolo[5,4-b]pyridine:

• Personal protective equipment (PPE): Wear appropriate gloves, lab coat, and eye protection when handling the compound. Avoid inhalation of dust or vapors.
• Storage: Store in a cool, dry, well-ventilated area, away from heat sources and incompatible materials (strong oxidizers, strong bases). Keep the container tightly closed. Refrigerated storage (2–8 °C) is generally recommended for long-term stability of sensitive heterocyclic intermediates.
• Disposal: Dispose of in accordance with local, regional, and national regulations for chemical waste.
• SDS: Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard information before use.

Please refer to the product page for the most current SDS and purity certificate (CoA) for SKU B187737.

Ordering and Availability

6-Bromothiazolo[5,4-b]pyridine is available from Aladdin Scientific under SKU B187737. To place an order or request a quotation:

• Visit the Aladdin Scientific website and search for SKU B187737 or the compound name.
• Contact your local Aladdin Scientific sales representative for bulk pricing, custom packaging, or expedited delivery inquiries.
• Registered account holders can manage orders, track shipments, and access invoices through the online account portal.

For questions regarding purity specifications, certificates of analysis (CoA), or regulatory documentation, please contact Aladdin Scientific technical support.

Frequently asked questions

What is 6-Bromothiazolo[5,4-b]pyridine used for in research?

6-Bromothiazolo[5,4-b]pyridine is primarily used as a synthetic building block and intermediate in medicinal chemistry. Its aryl bromide handle enables palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig) to construct complex heterocyclic drug candidates. The thiazolopyridine scaffold is also explored in fragment-based drug design and materials science applications.

How should 6-Bromothiazolo[5,4-b]pyridine (SKU B187737) be stored to maintain stability?

For optimal stability, 6-Bromothiazolo[5,4-b]pyridine should be stored in a tightly sealed container in a cool, dry, and well-ventilated location away from heat, moisture, and incompatible materials. Refrigerated storage at 2–8 °C is generally recommended for sensitive heterocyclic intermediates to ensure long-term integrity. Always consult the Aladdin Scientific SDS and CoA for lot-specific guidance.

What cross-coupling reactions can be performed using 6-Bromothiazolo[5,4-b]pyridine?

The C–Br bond in 6-Bromothiazolo[5,4-b]pyridine is well-suited for a range of palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura coupling with boronic acids, Buchwald–Hartwig amination for C–N bond formation, Negishi coupling with organozinc reagents, and Sonogashira coupling with terminal alkynes. These transformations allow rapid structural diversification of the thiazolopyridine core for SAR studies.

Is 6-Bromothiazolo[5,4-b]pyridine available in bulk quantities from Aladdin Scientific?

Yes, Aladdin Scientific can accommodate bulk quantity inquiries for 6-Bromothiazolo[5,4-b]pyridine (SKU B187737). Please contact your local Aladdin Scientific sales representative or reach out through the website to discuss pricing, availability, custom packaging, and lead times for larger quantities.

Where can I find the Safety Data Sheet (SDS) and Certificate of Analysis (CoA) for SKU B187737?

The Safety Data Sheet (SDS) and Certificate of Analysis (CoA) for 6-Bromothiazolo[5,4-b]pyridine (SKU B187737) are available on the Aladdin Scientific product page for this compound. You can download these documents directly from the website or request them from Aladdin Scientific technical support or your sales representative.

References

1. Aladdin Scientific Product Page: 6-Bromothiazolo[5,4-b]pyridine, SKU B187737.
2. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. General reference for thiazolopyridine ring systems.
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007

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