2-Bromo-5-nitrobenzoic Acid: Properties, Uses & FAQs

2-Bromo-5-nitrobenzoic Acid is a versatile halogenated aromatic carboxylic acid widely used as a key building block and intermediate in pharmaceutical synthesis, agrochemical research, and fine chemical manufacturing.

Chemical Name

2-Bromo-5-nitrobenzoic Acid

CAS Number

943-14-6

Molecular Formula

C₇H₄BrNO₄

Molecular Weight

246.01 g/mol

SKU

B152308

Functional Groups

Carboxylic acid, bromo, nitro on benzene ring

Primary Application

Pharmaceutical and agrochemical intermediate, cross-coupling substrate

Chemical Identity and Structure

2-Bromo-5-nitrobenzoic Acid (CAS 943-14-6, SKU B152308) is a substituted benzoic acid bearing a bromine atom at the ortho position (C-2) and a nitro group at the meta position relative to the carboxyl group (C-5). Its molecular formula is C₇H₄BrNO₄ with a molecular weight of approximately 246.01 g/mol. The compound typically appears as a pale yellow to off-white crystalline solid.

The combination of electron-withdrawing nitro and carboxylic acid groups significantly influences the electron density of the aromatic ring, making it reactive toward nucleophilic aromatic substitution and transition-metal-catalyzed cross-coupling reactions. The bromine atom serves as a handle for palladium-catalyzed reactions such as Suzuki–Miyaura, Heck, and Buchwald–Hartwig couplings.

Physicochemical Properties and Storage

2-Bromo-5-nitrobenzoic Acid is a solid at room temperature with a relatively high melting point consistent with its ability to form intermolecular hydrogen bonds through the carboxylic acid moiety. It exhibits limited solubility in water but dissolves readily in common polar organic solvents such as ethanol, acetone, ethyl acetate, and dimethyl sulfoxide (DMSO), as well as in dilute aqueous base due to deprotonation of the carboxylic acid group.

For long-term stability, the compound should be stored in a tightly sealed container in a cool, dry, well-ventilated area away from strong oxidizers, reducing agents, and incompatible bases. Standard laboratory storage conditions (room temperature to slightly below) are generally appropriate. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for specific handling and storage recommendations.

Applications in Synthesis and Research

As a bifunctional aromatic building block, 2-Bromo-5-nitrobenzoic Acid serves multiple roles in synthetic chemistry:

• Cross-coupling reactions: The C–Br bond participates in palladium- and nickel-catalyzed coupling reactions (Suzuki, Negishi, Sonogashira, Heck) to install aryl, alkenyl, or alkynyl substituents.
• Pharmaceutical intermediates: The nitro group can be selectively reduced to an amine, providing access to aminobenzoic acid derivatives used in drug synthesis, including heterocyclic scaffolds.
• Nucleophilic aromatic substitution (SNAr): The presence of two electron-withdrawing groups activates the ring toward displacement of the bromine by appropriate nucleophiles under suitable conditions.
• Agrochemical and materials research: The compound acts as a precursor for ligands, dyes, and functional polymers that require precisely substituted aromatic cores.

Researchers should optimize reaction conditions—catalyst loading, base, solvent, and temperature—for each specific transformation to maximize yield and selectivity.

Safety, Handling, and Regulatory Considerations

2-Bromo-5-nitrobenzoic Acid contains a nitro group, which confers potential hazards that users must address. Key precautions include:

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves, safety goggles, and a lab coat. Work in a fume hood to minimize inhalation of dust or vapors.
• Irritancy: The compound may cause skin, eye, and respiratory tract irritation. In the event of skin or eye contact, wash thoroughly with water and seek medical attention if irritation persists.
• Waste disposal: Dispose of waste in accordance with local, regional, and national regulations. Do not pour down drains.
• SDS: Always consult the current Safety Data Sheet provided by Aladdin Scientific before first use. The SDS contains authoritative information on hazard classification, first-aid measures, and spill procedures.

Specific GHS hazard classifications and pictograms should be confirmed in the product SDS, as these may vary by jurisdiction and lot.

Ordering, Specification, and Quality

2-Bromo-5-nitrobenzoic Acid is available from Aladdin Scientific under SKU B152308. When placing an order, researchers and procurement staff should confirm:

• Purity grade: Check the certificate of analysis (CoA) for purity data, typically verified by HPLC or GC. Contact Aladdin Scientific's technical team if a specific purity grade (e.g., ≥98%) is required for your application.
• Pack sizes: Multiple pack sizes may be available. Select based on projected usage to optimize cost and minimize waste from repeated opening.
• Lot-to-lot consistency: Request CoA documentation for each lot to verify identity (NMR, MS) and purity before use in critical assays or scale-up synthesis.
• Lead time and shipping: Confirm availability and estimated delivery with your regional Aladdin Scientific representative. The compound should be shipped in a way that maintains integrity—typically at ambient temperature with desiccant, though specific conditions should be verified with the supplier.

For bulk quantities, custom purity specifications, or regulatory documentation needs, contact Aladdin Scientific's sales or technical support team directly.

Frequently asked questions

What is 2-Bromo-5-nitrobenzoic Acid used for in organic synthesis?

2-Bromo-5-nitrobenzoic Acid is primarily used as a bifunctional building block in pharmaceutical and fine chemical synthesis. The bromine atom enables palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Heck, Sonogashira), while the nitro group can be selectively reduced to an amine for further derivatization. It also undergoes nucleophilic aromatic substitution owing to the electron-withdrawing groups on the ring.

What solvents are suitable for dissolving 2-Bromo-5-nitrobenzoic Acid?

2-Bromo-5-nitrobenzoic Acid has limited water solubility but dissolves well in polar organic solvents including ethanol, acetone, ethyl acetate, and DMSO. It can also dissolve in dilute aqueous sodium hydroxide or potassium carbonate solutions due to deprotonation of its carboxylic acid group. Solvent choice should be guided by the downstream reaction requirements.

How should 2-Bromo-5-nitrobenzoic Acid (B152308) be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location away from strong oxidizers, reducing agents, and incompatible bases. Standard ambient laboratory storage conditions are generally adequate for short- to medium-term storage. Always refer to the Aladdin Scientific SDS for authoritative storage guidance specific to each lot.

What safety precautions should I take when handling 2-Bromo-5-nitrobenzoic Acid?

Users should wear chemical-resistant gloves, safety goggles, and a lab coat, and handle the compound in a fume hood to avoid inhalation of dust or vapors. The nitro-containing compound may be an irritant to skin, eyes, and respiratory tract. In case of contact, rinse with copious water and seek medical advice if needed. Dispose of waste according to applicable regulations and consult the product SDS for full hazard information.

How can I verify the purity and identity of the 2-Bromo-5-nitrobenzoic Acid I receive?

Aladdin Scientific provides a Certificate of Analysis (CoA) with each lot, which includes purity data typically determined by HPLC or GC, along with identity confirmation by spectroscopic methods such as NMR or MS. Researchers can also perform independent verification using melting point determination, IR spectroscopy, or HPLC against a reference standard. Contact Aladdin Scientific's technical support team if additional documentation is needed.

Is 2-Bromo-5-nitrobenzoic Acid (B152308) available in bulk quantities or custom purity grades?

Aladdin Scientific may offer multiple pack sizes and can accommodate bulk or custom requests depending on inventory and production capacity. Researchers or procurement teams requiring non-standard pack sizes, higher purity grades, or specific regulatory documentation should contact Aladdin Scientific's sales team directly to discuss availability, lead times, and pricing.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for electrophilic aromatic substitution and cross-coupling reactions.
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. Foundational reference for Suzuki–Miyaura coupling applicable to aryl bromides. doi:10.1021/cr00039a007
3. Aladdin Scientific. Certificate of Analysis and Safety Data Sheet for 2-Bromo-5-nitrobenzoic Acid, SKU B152308. Aladdin Scientific internal documentation.

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