2,6-Bis(Trifluoromethyl)Benzoic Acid: Properties & Lab Uses
2,6-Bis(Trifluoromethyl)Benzoic Acid: Properties & Lab Uses
2,6-Bis(Trifluoromethyl)Benzoic Acid is a highly fluorinated aromatic carboxylic acid featuring two electron-withdrawing trifluoromethyl groups flanking the carboxyl function, making it a valuable building block in organofluorine synthesis and medicinal chemistry research.
- Chemical Name
- 2,6-Bis(Trifluoromethyl)Benzoic Acid
- Molecular Formula
- C9H4F6O2
- Molecular Weight
- 258.12 g/mol
- Key Functional Groups
- Carboxylic acid (–COOH) and two trifluoromethyl groups (–CF3)
- Aladdin SKU
- B770238
- Typical Application
- Organofluorine synthesis, pharmaceutical intermediate, agrochemical research
Chemical Structure and Properties
2,6-Bis(Trifluoromethyl)Benzoic Acid is an aromatic carboxylic acid in which both the 2- and 6-positions of the benzene ring bear trifluoromethyl (–CF3) substituents, with a carboxyl group (–COOH) at the 1-position. The strong electron-withdrawing nature of the two flanking –CF3 groups significantly increases the acidity of the carboxylic acid relative to unsubstituted benzoic acid, lowering the pKa and enhancing its reactivity as an electrophilic coupling partner.
The high fluorine content imparts low surface energy, improved metabolic stability in biological systems, and increased lipophilicity compared to non-fluorinated analogues. The steric bulk of the two ortho –CF3 groups also introduces conformational constraints that can influence the geometry of downstream synthetic targets. These combined electronic and steric effects make this compound a uniquely versatile reagent in the design of fluorinated molecules.
Research Applications
The primary utility of 2,6-Bis(Trifluoromethyl)Benzoic Acid lies in its role as a synthetic building block for the preparation of complex fluorinated molecules. Researchers in medicinal chemistry exploit the compound's activated carboxylic acid group for amide bond formation, esterification, and further functional group transformations to access fluorinated pharmacophores with improved bioavailability and metabolic resistance.
In agrochemical research, highly fluorinated benzoic acid derivatives are investigated as precursors to herbicides, fungicides, and insecticides, where the fluorine substituents modulate biological activity and environmental persistence. The compound is also of interest in materials science, where organofluorine building blocks contribute to the synthesis of high-performance polymers, surfactants, and specialty coatings. Additionally, it serves as a reference standard and model compound in physical-organic chemistry studies probing the interplay between fluorine substitution, acidity, and molecular geometry.
Handling, Storage, and Safety
As with most fluorinated aromatic carboxylic acids, 2,6-Bis(Trifluoromethyl)Benzoic Acid should be handled with standard laboratory precautions. Personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat is recommended when weighing or transferring the compound. Operations generating dust or aerosols should be conducted in a chemical fume hood to prevent inhalation.
The compound should be stored in a tightly sealed container in a cool, dry environment away from strong bases, strong oxidizing agents, and moisture. Fluorinated carboxylic acids can react with reactive metals to liberate hydrogen gas; therefore, contact with alkali metals and strong reducing agents should be avoided. Disposal must comply with applicable local, national, and institutional regulations for fluorinated organic waste. Consult the Safety Data Sheet (SDS) provided with the product for comprehensive hazard information before use.
Ordering Information and Specifications
Aladdin Scientific supplies 2,6-Bis(Trifluoromethyl)Benzoic Acid under SKU B770238. Researchers and procurement teams are encouraged to verify current purity specifications, available pack sizes, and pricing through the Aladdin Scientific online catalog or by contacting customer service directly. Standard documentation including Certificate of Analysis (CoA) and Safety Data Sheet (SDS) is available upon request.
For bulk quantities or custom purity grades required for GMP or specialized research programs, please reach out to the Aladdin Scientific sales team to discuss tailored supply solutions. Ensure that the reagent grade selected is appropriate for the intended application, particularly for assay development or reference standard use where certified purity is critical.
Frequently asked questions
What makes 2,6-Bis(Trifluoromethyl)Benzoic Acid useful as a synthetic building block?
The two electron-withdrawing –CF3 groups at the ortho positions activate the carboxylic acid toward nucleophilic acyl substitution reactions, facilitating amide and ester formation. The high fluorine content simultaneously confers metabolic stability and tunable lipophilicity to target molecules derived from this scaffold.
How should 2,6-Bis(Trifluoromethyl)Benzoic Acid be stored to maintain reagent integrity?
The compound should be kept in a tightly sealed container under cool, dry conditions, away from moisture, strong bases, and oxidizing agents. Adherence to these conditions minimizes hydrolytic degradation and ensures long-term stability of the reagent.
Is 2,6-Bis(Trifluoromethyl)Benzoic Acid suitable for medicinal chemistry applications?
Yes, this compound is well-suited for medicinal chemistry programs where fluorinated aromatic scaffolds are required. The –CF3 substituents improve the metabolic stability and membrane permeability of derived compounds, properties that are highly desirable in drug discovery. Researchers should confirm purity specifications from the Certificate of Analysis before use in biological assays.
What is the Aladdin Scientific catalog number for 2,6-Bis(Trifluoromethyl)Benzoic Acid?
The Aladdin Scientific catalog SKU for 2,6-Bis(Trifluoromethyl)Benzoic Acid is B770238. Customers can use this SKU to search the online catalog, request a quote, or place an order directly.
References
- Müller K, Faeh C, Diederich F. Fluorine in pharmaceuticals: looking beyond intuition. Science. 2007;317(5846):1881-1886. doi:10.1126/science.1131943
- Purser S, Moore PR, Swallow S, Gouverneur V. Fluorine in medicinal chemistry. Chem Soc Rev. 2008;37(2):320-330. doi:10.1039/b610213c
- Aladdin Scientific Product Catalog. 2,6-Bis(Trifluoromethyl)Benzoic Acid, SKU B770238. Aladdin Scientific.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）