Chemical Identity and Properties

2-Bromo-4-(tert-butyl)benzoic acid is an aromatic carboxylic acid bearing two key substituents on the benzene ring: a bromine atom at the ortho position (C-2) and a tert-butyl group at the para position (C-4) relative to the carboxylic acid group. The tert-butyl group is a bulky, electron-donating alkyl substituent that enhances the lipophilicity of the molecule and influences the electronic density of the aromatic ring, while the bromine atom at C-2 provides a reactive handle for metal-catalyzed transformations.

The compound is typically encountered as a white to off-white crystalline solid or powder at room temperature. The carboxylic acid functionality confers moderate acidity to the molecule, making it soluble in polar organic solvents such as ethanol, methanol, dimethyl sulfoxide (DMSO), and ethyl acetate, with limited solubility in water. Researchers should verify specific physicochemical constants (e.g., exact melting point, pKa) against the certificate of analysis supplied with each lot.

Synthetic Applications and Reactivity

The C–Br bond in 2-Bromo-4-(tert-butyl)benzoic acid is the primary site of reactivity, enabling a broad range of transition-metal-catalyzed transformations that are central to modern medicinal chemistry and materials science. Key reaction classes include:

• Suzuki–Miyaura Coupling: Reaction with aryl- or alkenylboronic acids under palladium catalysis to construct biaryl or styryl frameworks.
• Buchwald–Hartwig Amination: Palladium-catalyzed C–N bond formation with amines to yield arylamines of pharmaceutical relevance.
• Sonogashira Coupling: Coupling with terminal alkynes in the presence of palladium and copper co-catalysts to produce aryl alkynes.
• Carbonylation Reactions: Conversion of the aryl bromide to esters, amides, or aldehydes via CO insertion under palladium catalysis.

The carboxylic acid group itself can be activated (e.g., as an acid chloride, active ester, or mixed anhydride) for amide bond formation, esterification, or Curtius-type rearrangements, expanding the compound's utility as a bifunctional building block.

The tert-butyl group may also be removed under strongly acidic conditions (e.g., trifluoroacetic acid or concentrated sulfuric acid), providing access to the corresponding unsubstituted brominated benzoic acid if required in a synthetic sequence.

Safe Handling, Storage, and Disposal

Personal Protective Equipment (PPE): When handling 2-Bromo-4-(tert-butyl)benzoic acid, wear appropriate chemical-resistant gloves (e.g., nitrile), a laboratory coat, and safety glasses or goggles. Work in a fume hood when weighing or transferring the compound to avoid inhalation of fine dust particles.

Storage: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, oxidizing agents, and strong bases. Segregate from incompatible materials. Check the product-specific Safety Data Sheet (SDS) for exact hazard classifications and pictograms, as these may vary by lot and regulatory jurisdiction.

Disposal: Dispose of this compound and contaminated materials in accordance with local, national, and institutional regulations governing halogenated organic waste. Do not pour down the drain. Consult your institution's Environmental Health and Safety (EHS) office for approved disposal procedures.

First Aid: In case of skin contact, wash thoroughly with soap and water. For eye contact, flush with copious amounts of water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air immediately. Always consult the SDS for comprehensive first-aid measures.

Quality, Purity, and Procurement Guidance

For reproducible research outcomes, the purity of 2-Bromo-4-(tert-butyl)benzoic acid is a critical parameter. Aladdin Scientific supplies this reagent under SKU B589743. Researchers should request and review the Certificate of Analysis (CoA) for each lot, which typically includes identity confirmation (e.g., NMR, HPLC, or GC data), purity determination, and physical characterization data.

Recommended quality checks before use:

• Confirm identity by comparing melting point or NMR data against literature or internal reference standards.
• Assess purity by HPLC or GC to detect potential impurities, including regioisomers or residual starting materials from synthesis.
• Inspect physical appearance: the compound should be free of discoloration or clumping that may indicate degradation due to moisture exposure.

Procurement tip: Order quantities appropriate to your project timeline. Although the compound is relatively stable when stored correctly, purchasing smaller quantities more frequently minimizes the risk of degradation over time. Contact Aladdin Scientific customer service for bulk pricing, custom pack sizes, or availability inquiries.