6-Bromopyridine-2-sulfonyl Chloride: Key Facts & FAQs

6-Bromopyridine-2-sulfonyl chloride is a bifunctional heterocyclic reagent bearing both a reactive sulfonyl chloride group and a bromo substituent, making it a versatile building block for the synthesis of sulfonamides, sulfonate esters, and further cross-coupling products.

CAS Number

Not confirmed in source material — needs review

Molecular Formula

C₅H₃BrClNO₂S

Molecular Weight

Approximately 256.51 g/mol (needs verification)

Key Functional Groups

Sulfonyl chloride (–SO₂Cl) and aryl bromide (–Br)

Primary Applications

Sulfonamide synthesis, sulfonate ester formation, Pd-catalyzed cross-coupling via the C–Br bond

Storage Conditions

Store in a cool, dry place; protect from moisture; refrigeration recommended (needs confirmation from SDS)

SKU

B732106

What Is 6-Bromopyridine-2-sulfonyl Chloride?

6-Bromopyridine-2-sulfonyl chloride is a pyridine-based heterocyclic compound that carries two orthogonal reactive handles: a sulfonyl chloride (–SO₂Cl) group at the 2-position and a bromine atom at the 6-position of the pyridine ring. This dual functionality distinguishes it from simpler sulfonyl chlorides and makes it particularly attractive as a bifunctional building block in medicinal chemistry, agrochemical research, and materials science.

The sulfonyl chloride moiety is highly electrophilic and reacts readily with nucleophiles such as amines (to form sulfonamides), alcohols (to form sulfonate esters), and thiols. The aryl bromide at the 6-position can participate in palladium-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig), enabling sequential or orthogonal functionalization of the molecule.

Key Chemical Properties and Handling Precautions

As an acyl-type electrophile, the sulfonyl chloride group in 6-bromopyridine-2-sulfonyl chloride is susceptible to hydrolysis upon exposure to moisture or water, generating the corresponding sulfonic acid and hydrochloric acid. Researchers should therefore handle this reagent under anhydrous conditions and in an appropriate dry solvent such as dichloromethane (DCM), tetrahydrofuran (THF), or acetonitrile.

Personal Protective Equipment (PPE): Because the reagent can release HCl upon hydrolysis, adequate ventilation, chemical splash goggles, acid-resistant gloves, and a laboratory coat are required. Reactions should ideally be conducted in a fume hood.

Incompatibilities: Avoid contact with water, strong bases, and strong nucleophiles unless they are the intended reaction partners. Consult the Safety Data Sheet (SDS) for full hazard and first-aid information before use. Specific GHS classifications and hazard codes are not confirmed in the current source material and should be verified against the product SDS.

Synthetic Applications in Research

The combination of a sulfonyl chloride and an aryl bromide on a pyridine scaffold opens multiple pathways for library synthesis and target-oriented synthesis:

• Sulfonamide formation: Treatment with primary or secondary amines under mild base conditions (e.g., triethylamine, pyridine) furnishes N-substituted sulfonamides bearing the 6-bromopyridine core, which can then be further elaborated via cross-coupling.
• Sequential cross-coupling: The C–Br bond at C-6 is compatible with a wide range of palladium and nickel catalysis protocols, including Suzuki–Miyaura (boronic acids), Negishi (organozinc), and Sonogashira (terminal alkynes) couplings. This allows rapid diversification of the pyridine core after sulfonylation.
• Sulfonate ester synthesis: Reaction with phenols or aliphatic alcohols, typically in the presence of a base, produces sulfonate esters useful as leaving groups or pharmacophore elements.
• Heterocycle elaboration: The pyridine nitrogen may act as a coordination site or undergo N-alkylation, providing additional vectors for molecular diversification.

These features make B732106 a high-value intermediate in fragment-based drug discovery, agrochemical lead optimization, and the preparation of sulfonamide-containing bioactive compounds.

Storage, Stability, and Quality

Recommended storage: Store in a tightly sealed container under inert atmosphere (nitrogen or argon), in a cool, dry location away from moisture and incompatible materials. Refrigerated storage (2–8 °C) is generally advisable for sulfonyl chloride reagents to retard slow hydrolysis; however, users should confirm specific conditions from the product label and SDS provided by Aladdin Scientific.

Stability: Sulfonyl chlorides are generally stable when stored properly but can degrade if repeatedly exposed to ambient humidity. Aliquoting into single-use portions is recommended for long-term stock management.

Purity and specification: Aladdin Scientific provides purity specifications (typically ≥95% or per certificate of analysis); buyers are encouraged to request a Certificate of Analysis (CoA) for each lot. Exact purity figures for B732106 are not detailed in the current source material and should be confirmed with Aladdin Scientific's product team.

Ordering and Procurement Information

6-Bromopyridine-2-sulfonyl chloride is available from Aladdin Scientific under SKU B732106. Researchers and procurement teams can place orders through the Aladdin Scientific website or by contacting the sales team directly. Bulk quantities and custom packaging may be available upon request.

When ordering, please confirm the required quantity, desired purity grade, and any special packaging requirements (e.g., ampoule, Sure/Seal bottle) with your Aladdin Scientific representative to ensure the reagent arrives in optimal condition for your application.

For questions about pricing, promotions, or institutional accounts, please consult the Aladdin Scientific customer service team or visit the product page for the most current information.

Frequently asked questions

What is the difference between the sulfonyl chloride and the aryl bromide in 6-Bromopyridine-2-sulfonyl chloride, and can I react them independently?

Yes. The sulfonyl chloride (–SO₂Cl) is a highly electrophilic acyl-type group that reacts rapidly with nucleophiles such as amines, alcohols, and thiols under mild conditions. The aryl bromide (C–Br) at the 6-position is relatively inert toward nucleophiles but is an excellent partner for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, Sonogashira). By choosing reaction conditions selectively, researchers can functionalize each site independently or in sequence.

How should I handle 6-Bromopyridine-2-sulfonyl chloride safely in the laboratory?

This reagent should be handled under anhydrous conditions in a well-ventilated fume hood. Wear chemical splash goggles, acid-resistant gloves, and a lab coat, as hydrolysis releases HCl, which is corrosive. Consult the Safety Data Sheet (SDS) supplied with the product for complete hazard classification, first-aid measures, and disposal procedures before use.

What solvents are recommended for reactions involving 6-Bromopyridine-2-sulfonyl chloride?

Anhydrous aprotic solvents are strongly preferred to prevent premature hydrolysis of the sulfonyl chloride. Commonly used solvents include dry dichloromethane (DCM), tetrahydrofuran (THF), acetonitrile, and toluene. Protic solvents and water should be avoided unless the intent is hydrolysis.

What is the best way to store 6-Bromopyridine-2-sulfonyl chloride to maintain its reactivity?

Store the reagent in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C, away from moisture. For long-term storage, aliquoting into single-use portions minimizes repeated exposure of the bulk material to air and humidity. Always confirm storage conditions with the Aladdin Scientific product label and SDS.

Can 6-Bromopyridine-2-sulfonyl chloride (B732106) be used in palladium-catalyzed cross-coupling reactions?

Yes. The aryl C–Br bond at the 6-position of the pyridine ring is well-suited for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura (with boronic acids), Negishi (with organozincs), and Sonogashira (with terminal alkynes). This reactivity allows researchers to introduce diverse aryl, heteroaryl, vinyl, or alkynyl groups at C-6 after or before sulfonyl chloride functionalization, enabling efficient library synthesis.

References

1. Aladdin Scientific product page for 6-Bromopyridine-2-sulfonyl chloride, SKU B732106.
2. General reference: March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (Sulfonyl chloride reactivity and sulfonamide synthesis.)
3. General reference: 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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