Chemical Identity and Structure

3-Bromo-4-(difluoromethyl)benzoic acid is an aromatic carboxylic acid bearing two distinct halogen-based substituents on the benzene ring: a bromine atom at the 3-position and a difluoromethyl (–CHF2) group at the 4-position, with the carboxylic acid (–COOH) functionality at the 1-position. Its molecular formula is C₈H₅BrF₂O₂ and its approximate molecular weight is 267.03 g/mol.

The difluoromethyl group is bioisosteric with hydroxyl, thiol, and other hydrogen-bond donors in drug design contexts, and it imparts significant metabolic stability and lipophilicity modulation to molecules incorporating it. The aryl bromide handle at the 3-position renders the compound suitable for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings. Together, these features make this compound a bifunctional scaffold of considerable synthetic value.

Physicochemical Properties and Handling

As a difluoromethyl- and bromo-substituted benzoic acid, this compound is expected to be a solid at room temperature with moderate solubility in polar organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), ethanol, and ethyl acetate. Solubility in water is expected to be low due to the hydrophobic difluoromethyl substituent, though the carboxylic acid group provides some capacity for salt formation under basic aqueous conditions.

The carboxylic acid moiety confers mild acidity. Researchers should handle the compound with standard laboratory precautions: use of nitrile gloves, safety glasses, and a laboratory coat is recommended. Operations should be conducted in a well-ventilated fume hood. The compound should be stored in a tightly sealed container in a cool, dry environment. Always consult the Safety Data Sheet (SDS) for SKU B732213 before use for authoritative hazard classification, first-aid measures, and disposal guidance.

Note: Specific melting point, boiling point, logP, and pKa values are not available in the current source material and should be verified from the product specification sheet or peer-reviewed literature before citation.

Synthetic Applications and Reactivity

3-Bromo-4-(difluoromethyl)benzoic acid offers three orthogonal sites for chemical elaboration, making it a highly attractive intermediate in multi-step synthesis programs:

• Aryl bromide (C3): The C–Br bond is well-suited for palladium- or nickel-catalyzed cross-coupling reactions. Suzuki–Miyaura coupling with aryl or alkyl boronic acids, Negishi coupling with organozinc reagents, and Buchwald–Hartwig amination for C–N bond formation are all accessible. Sonogashira coupling with terminal alkynes is also feasible.
• Difluoromethyl group (C4): The –CHF2 group is chemically stable under most standard synthetic conditions. Its presence modulates the electronic density of the aromatic ring and influences the reactivity of adjacent functional groups.
• Carboxylic acid (C1): The –COOH group can be converted to acid chlorides, esters, amides, or reduced to aldehydes and alcohols via standard transformations. It can also serve as a handle for coupling to amine-containing pharmacophores via amide bond formation.

These combined reactivities allow the construction of complex fluorinated scaffolds relevant to drug discovery and agrochemical lead optimization.

Applications in Drug Discovery and Agrochemistry

The incorporation of fluorine-containing groups into biologically active molecules is a well-established strategy in pharmaceutical and agrochemical research. The difluoromethyl group in particular mimics hydrogen-bond donor groups (such as –OH or –NH) while offering superior metabolic stability, making it a prized motif in modern drug design.

3-Bromo-4-(difluoromethyl)benzoic acid is therefore positioned as a useful building block for:

• Medicinal chemistry: Generation of fluorinated drug candidates targeting enzyme active sites or receptor binding pockets where –CHF2 acts as a bioisostere. The carboxylic acid enables rapid amide library synthesis for structure–activity relationship (SAR) studies.
• Agrochemical synthesis: Fluorinated benzoic acid derivatives appear frequently in herbicide, fungicide, and insecticide scaffolds. This compound can serve as an intermediate toward such targets.
• Fragment-based drug discovery (FBDD): The compact, multifunctional structure and defined molecular weight make it a candidate fragment for screening campaigns.

Researchers engaged in late-stage functionalization strategies will find the aryl bromide particularly useful for diversifying a core scaffold without disturbing the –CHF2 or –COOH groups.

Ordering and Quality Information

3-Bromo-4-(difluoromethyl)benzoic acid is available from Aladdin Scientific under SKU B732213. When placing an order, researchers and procurement teams should confirm the following with the product specification sheet:

• Purity grade and analytical method (e.g., HPLC, NMR)
• Available pack sizes and pricing
• Lot-specific Certificate of Analysis (CoA)
• Current inventory and lead times

For bulk quantities, custom synthesis inquiries, or technical questions regarding this compound, contact Aladdin Scientific's technical support team. All products are subject to Aladdin Scientific's standard quality control procedures. Safety Data Sheets (SDS) and Certificates of Analysis are available upon request or via the product page on the Aladdin Scientific website.