Chemical Identity and Structure

3-Amino-4-(trifluoromethyl)benzoic acid (CAS 127163-22-8, MW 205.13 g/mol, molecular formula C₈H₆F₃NO₂) is a substituted benzoic acid in which a primary amino group occupies the 3-position and a trifluoromethyl group occupies the 4-position of the aromatic ring. The compound combines three synthetically valuable handles: the electron-withdrawing –CF₃ group, the nucleophilic –NH₂ group, and the electrophilic –COOH group. This combination of substituents gives the molecule an amphoteric character and makes it particularly useful in the construction of more complex drug-like scaffolds. The strong electron-withdrawing nature of the trifluoromethyl group lowers the pKa of the carboxylic acid and reduces the basicity of the amine relative to unsubstituted aminobenzoic acids, which are considerations when planning coupling or protection strategies.

Research Applications

The dual functionality of 3-Amino-4-(trifluoromethyl)benzoic acid makes it a sought-after building block in several research domains:

• Medicinal chemistry: The –CF₃ group is a well-established bioisostere that enhances metabolic stability and membrane permeability of drug candidates. The free amine and acid groups allow straightforward elaboration via amide bond formation, reductive amination, esterification, diazotization, or heterocycle synthesis, enabling rapid construction of diverse compound libraries.
• Heterocyclic synthesis: The ortho-relationship between the –NH₂ and –CF₃ groups, combined with the –COOH, can be exploited in cyclization reactions to form benzimidazoles, quinazolinones, and related nitrogen-containing heterocycles.
• Materials science: Fluorinated aromatic monomers are incorporated into high-performance polymers, liquid crystals, and functional materials to tune solubility, thermal stability, and optical properties.
• Agrochemical research: Fluorinated benzoic acid derivatives serve as key intermediates in the synthesis of herbicides, fungicides, and insecticides.

Researchers should note that specific biological activity data for this compound are not currently available in Aladdin's product documentation; intended use should be validated in the user's own assay system.

Handling, Storage, and Safety

Handling precautions: As with all primary aromatic amines, 3-Amino-4-(trifluoromethyl)benzoic acid should be handled with appropriate personal protective equipment including gloves, lab coat, and eye protection. Avoid inhalation of dust. Work in a well-ventilated area or fume hood. Aromatic amines as a class may have sensitization or mutagenic potential; consult the Safety Data Sheet (SDS) before first use.

Storage: Store in a tightly sealed container in a cool (15–25 °C), dry, well-ventilated location away from light, heat, oxidizing agents, and strong acids or bases. Under these conditions, the solid is expected to be stable for an extended period; however, users should inspect the material for discoloration before use, as aromatic amines can oxidize gradually.

Disposal: Dispose of in accordance with local environmental regulations for organic chemical waste. Do not discharge into drains or waterways.

Note: Always refer to the current Aladdin SDS for the most up-to-date hazard, first-aid, and regulatory information specific to this product.

Purity, Specifications, and Quality

Aladdin Scientific supplies 3-Amino-4-(trifluoromethyl)benzoic acid (SKU A190317) as a research-grade reagent. Typical quality attributes for this class of compound include:

• Purity: Verified by HPLC or GC analysis; please refer to the Certificate of Analysis (CoA) supplied with each lot for the actual purity value, as specifications may vary by pack size or catalog revision.
• Identity confirmation: Structural identity is typically confirmed by ¹H NMR, ¹⁹F NMR, and/or mass spectrometry.
• Appearance: Off-white to pale yellow crystalline powder.

If your application requires a higher-purity grade (e.g., ≥99% for crystallographic studies), contact Aladdin's technical support team to discuss available options. Lot-specific CoA documents can be requested via the product page or customer service.