4-Bromo-N-phenylbenzenesulfonamide: Properties & Lab FAQ

4-Bromo-N-phenylbenzenesulfonamide is an aryl sulfonamide building block bearing a para-bromo substituent on the sulfonyl-bearing ring, making it a versatile intermediate for cross-coupling reactions, medicinal chemistry, and the synthesis of more complex sulfonamide derivatives.

Chemical Name

4-Bromo-N-phenylbenzenesulfonamide

SKU / Catalog Number

B698076

Molecular Formula

C₁₂H₁₀BrNO₂S

Molecular Weight

312.18 g/mol

Functional Class

Aryl sulfonamide; cross-coupling precursor

Key Structural Feature

Para-bromo on sulfonyl phenyl ring; N–H sulfonamide linkage

Chemical Identity and Structure

4-Bromo-N-phenylbenzenesulfonamide (CAS number to be confirmed; SKU B698076) belongs to the diaryl sulfonamide class. Its structure consists of a 4-bromobenzenesulfonyl group covalently attached via the sulfonamide nitrogen to an unsubstituted phenyl ring. The para-bromo substituent is particularly valuable because it acts as a handle for palladium-catalysed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Heck transformations, enabling efficient diversification of the aromatic core. The sulfonamide N–H proton (pKa approximately 16–18 in DMSO for diaryl sulfonamides) can also be deprotonated for N-alkylation chemistry.

Physical Properties and Storage

4-Bromo-N-phenylbenzenesulfonamide is typically a white to off-white crystalline solid at ambient temperature. Diaryl sulfonamides of this type generally exhibit moderate to good solubility in polar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), and tetrahydrofuran (THF), and lower solubility in water and non-polar solvents such as hexane. For long-term storage, the compound should be kept in a tightly sealed container away from moisture and light at room temperature or under refrigeration (2–8 °C). Verify exact recommended storage conditions on the product label or certificate of analysis supplied with your order.

Note: Always consult the current Safety Data Sheet (SDS) before handling.

Research and Synthetic Applications

The compound serves primarily as a synthetic intermediate in organic and medicinal chemistry. Key application areas include:

• Cross-coupling chemistry: The aryl bromide moiety undergoes palladium-catalysed Suzuki, Negishi, Heck, and Buchwald–Hartwig reactions to install diverse aryl, vinyl, or amino groups at the 4-position of the sulfonyl ring.
• Sulfonamide library synthesis: N-Alkylation or N-acylation of the sulfonamide nitrogen generates a wide variety of N-substituted diaryl sulfonamide analogues for structure–activity relationship (SAR) studies.
• Pharmaceutical and agrochemical intermediates: Sulfonamide motifs are prevalent in approved drugs and crop-protection agents; this compound can serve as a precursor to biologically active targets.
• Coordination chemistry: Sulfonamide nitrogen donors have been utilised as ligands in metal-complex formation.

Handling, Safety, and Regulatory Considerations

As with all fine chemicals, standard laboratory precautions apply. Use appropriate personal protective equipment (PPE) including gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood. The compound contains an organobromine functionality; although aryl sulfonamides are generally of moderate hazard, the specific GHS classification should be confirmed on the product SDS prior to use. Dispose of waste in accordance with local environmental regulations governing halogenated organic compounds.

This product is intended for research use only and is not approved for human, veterinary, or food/agricultural use.

Ordering and Quality Assurance

4-Bromo-N-phenylbenzenesulfonamide is available from Aladdin Scientific under catalog number B698076. Each lot is supported by a certificate of analysis (CoA) documenting identity confirmation (e.g., by NMR or HPLC) and purity. Researchers requiring higher purity grades or custom pack sizes should contact Aladdin Scientific's technical sales team. Bulk and custom synthesis enquiries are also welcome. For procurement teams, standard lead times and pricing are available through the Aladdin Scientific website or upon request.

Frequently asked questions

What is 4-Bromo-N-phenylbenzenesulfonamide used for in organic synthesis?

It is primarily used as a bifunctional building block: the aryl bromide enables palladium-catalysed cross-coupling reactions (e.g., Suzuki, Heck, Buchwald–Hartwig), while the sulfonamide N–H can be further functionalised via N-alkylation or N-acylation. Together, these handles make it valuable for constructing sulfonamide-containing libraries for medicinal chemistry and SAR studies.

What solvents are recommended for dissolving 4-Bromo-N-phenylbenzenesulfonamide?

Diaryl sulfonamides of this type generally dissolve well in polar aprotic solvents such as DMSO, DMF, and THF. Solubility in water and non-polar solvents such as hexane is typically low. Always perform a small-scale solubility test and confirm compatibility with your specific reaction or assay conditions.

How should 4-Bromo-N-phenylbenzenesulfonamide be stored to maintain stability?

Store the compound in a tightly sealed container, protected from moisture and light, at room temperature or under refrigeration (2–8 °C). Always refer to the product label and the current SDS for the most accurate and up-to-date storage recommendations specific to the lot you have received.

What purity grade is available for catalog number B698076, and how is it verified?

Each batch of B698076 is accompanied by a certificate of analysis (CoA) that documents purity, typically assessed by HPLC or NMR. For the exact purity specification of a specific lot, please download the CoA from the Aladdin Scientific website using the lot number printed on the product label.

Can 4-Bromo-N-phenylbenzenesulfonamide be used in Suzuki–Miyaura cross-coupling reactions?

Yes. The para-bromo substituent on the sulfonyl phenyl ring serves as an electrophilic partner in Suzuki–Miyaura reactions with aryl or vinyl boronic acids under standard palladium catalysis conditions. This provides direct access to 4-substituted diaryl sulfonamide products. Reaction optimisation (catalyst loading, base, solvent, temperature) should be performed according to established literature protocols.

References

1. Aladdin Scientific product page for 4-Bromo-N-phenylbenzenesulfonamide, SKU B698076.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. Wiley, 1992. (General sulfonamide chemistry reference.)
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007

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