Overview and Chemical Properties

2-(3-Bromophenyl)-1,3-thiazole-4-carboxylic acid (SKU B187731) is a bifunctional heterocyclic compound featuring a 1,3-thiazole core substituted at the 2-position with a meta-bromophenyl group and bearing a carboxylic acid at the 4-position. Its molecular formula is C₁₀H₆BrNO₂S with a molecular weight of approximately 284.13 g/mol.

The compound combines three synthetically valuable handles: (1) an aryl C–Br bond amenable to palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig); (2) a thiazole nitrogen and sulfur for coordination or further functionalization; and (3) a carboxylic acid suitable for amide bond formation, esterification, or decarboxylative transformations. This multifunctionality makes it a versatile building block in drug discovery and materials science programs.

Safety, PPE, and Handling Precautions

Although a comprehensive Safety Data Sheet (SDS) should be consulted before use, the following general precautions apply to brominated heteroaromatic carboxylic acids of this class:

• Personal Protective Equipment (PPE): Wear nitrile gloves, a laboratory coat, and safety glasses at all times when handling the compound.
• Ventilation: Handle in a well-ventilated fume hood to minimize inhalation of dust or aerosols.
• Skin and Eye Contact: Avoid direct contact. In case of skin contact, wash thoroughly with soap and water. In case of eye contact, rinse immediately with copious water and seek medical advice.
• Waste Disposal: Dispose of all waste in accordance with local institutional and regulatory guidelines for organic halide waste streams.

Note: Always refer to the current SDS supplied with the product for authoritative hazard information before commencing any experiment.

Storage and Stability

Proper storage is essential to maintain the integrity of 2-(3-Bromophenyl)-1,3-thiazole-4-carboxylic acid over time.

• Temperature: Store at 2–8 °C in a refrigerator dedicated to chemical storage.
• Container: Keep tightly sealed in the original container under an inert atmosphere (nitrogen or argon) if possible, particularly after first opening.
• Light and Moisture: Protect from prolonged exposure to light and atmospheric moisture, as aryl bromides can be susceptible to slow hydrolytic side reactions under harsh conditions.
• Shelf Life: Consult the Certificate of Analysis (CoA) and product label for the confirmed expiry date. Retest purity by HPLC or NMR if the compound has been stored for an extended period.

Prior to use, allow the sealed container to equilibrate to room temperature before opening to prevent condensation of atmospheric moisture onto the solid.

Solution Preparation and Common Synthetic Applications

Solubility and Solution Preparation: This compound is expected to show good solubility in polar aprotic solvents such as DMF, DMSO, and NMP, and moderate solubility in THF, EtOAc, and MeOH. Aqueous solubility is low at neutral pH but increases significantly upon deprotonation (pH > 7) due to carboxylate formation. Always verify solubility empirically before use and filter through a 0.2 µm PTFE syringe filter if preparing a stock solution for biological assays.

Common Synthetic Applications:

1. Amide Coupling: The carboxylic acid can be activated using standard coupling reagents (e.g., HATU, EDC/HOBt, T3P) to form amide bonds with primary or secondary amines, enabling rapid library synthesis of thiazole-containing amides relevant to medicinal chemistry.
2. Palladium-Catalyzed Cross-Coupling: The aryl bromide at the 3-position of the phenyl ring is an excellent electrophilic partner for Suzuki–Miyaura (with arylboronic acids), Negishi, or Heck reactions, allowing diversification of the biaryl scaffold.
3. Esterification: Treatment with alcohols under acid catalysis or via acyl chloride intermediates affords the corresponding esters, which may serve as protected carboxylic acid surrogates or prodrugs.

Recommended starting molar ratio for coupling reactions: Confirm conditions with a small-scale optimization experiment before scale-up. No specific literature values are available in the current source material — flag for experimental optimization.

Quality Control and Analytical Characterization

Each lot of 2-(3-Bromophenyl)-1,3-thiazole-4-carboxylic acid (B187731) from Aladdin Scientific is accompanied by a Certificate of Analysis (CoA) specifying purity and lot-specific data. Researchers should verify the following upon receipt:

• Purity: Confirm by HPLC (reverse-phase C18, UV detection at 254 nm or 214 nm). Expected purity ≥ 95% (see CoA for lot-specific value).
• Identity: Confirm by ¹H NMR in DMSO-d₆. Key signals include the thiazole ring proton (typically δ 8.2–8.5 ppm), aromatic protons of the bromophenyl ring (δ 7.6–8.1 ppm), and a broad carboxylic acid OH (δ 13–14 ppm). Confirm by ESI-MS: [M+H]⁺ expected at m/z 284/286 (isotope pattern characteristic of a mono-bromine compound).
• Appearance: Off-white to pale yellow solid; discoloration or caking may indicate degradation.

Disclaimer: Specific NMR chemical shift values cited here are estimates based on structural analogy with related thiazole carboxylic acids and should be confirmed against the lot-specific CoA and primary literature.