2-Chloro-6-Fluorobenzoic Acid: Properties & Lab Uses

2-Chloro-6-fluorobenzoic Acid is a difunctionalized aromatic carboxylic acid bearing both chloro and fluoro substituents on the benzene ring, making it a versatile building block for pharmaceutical synthesis and materials research.

IUPAC Name

2-Chloro-6-fluorobenzoic acid

Molecular Formula

C₇H₄ClFO₂

Molecular Weight

174.56 g/mol

SKU / Product Code

C124485

Functional Groups

Carboxylic acid, aryl chloride, aryl fluoride

Appearance

White to off-white crystalline powder (typical)

Supplier

Aladdin Scientific

Chemical Identity and Structure

2-Chloro-6-fluorobenzoic acid is an ortho-disubstituted benzoic acid derivative in which a chlorine atom occupies the 2-position and a fluorine atom occupies the 6-position of the aromatic ring, flanking the carboxylic acid group on both sides. This 1,2,3-substitution pattern creates significant steric and electronic interactions that distinguish it from mono-halogenated analogues.

The carboxylic acid group (–COOH) confers acidity and hydrogen-bonding capacity, while the electron-withdrawing halogens lower the electron density of the ring and modulate the pKa relative to unsubstituted benzoic acid. The fluorine substituent, despite its small van der Waals radius, exerts a strong inductive withdrawal effect, whereas the chlorine provides a useful handle for further cross-coupling chemistry.

The compound is assigned the molecular formula C₇H₄ClFO₂ with a molecular weight of 174.56 g/mol. It is catalogued at Aladdin Scientific under SKU C124485.

Synthetic Utility and Reactivity

The combination of an activated aryl chloride and an aryl fluoride in the same molecule provides orthogonal reactivity: aryl fluorides undergo nucleophilic aromatic substitution (SNAr) more readily than aryl chlorides under basic conditions, while aryl chlorides are superior partners in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings.

The carboxylic acid can be converted to a wide range of functional derivatives including acid chlorides, esters, amides, and heterocyclic scaffolds. This versatility positions 2-chloro-6-fluorobenzoic acid as a key intermediate in multi-step pharmaceutical and agrochemical syntheses where selective elaboration of each substituent is required.

Sterically hindered ortho substituents adjacent to the –COOH group can influence the conformation of amide and ester products, a property exploited in the design of atropisomeric drug candidates and in the construction of conformationally restricted peptidomimetics.

Pharmaceutical and Research Applications

Halogenated benzoic acid derivatives are widely employed as intermediates in the synthesis of active pharmaceutical ingredients (APIs). Fluorine and chlorine substitution on aromatic rings is a common strategy in medicinal chemistry to optimize metabolic stability, membrane permeability, and target binding affinity. 2-Chloro-6-fluorobenzoic acid serves as a precursor in the preparation of fluorinated benzoxazoles, benzimidazoles, and other heterocyclic pharmacophores.

In agrochemical research, ortho-halogenated benzoic acids have been explored as building blocks for herbicides and fungicides, where the steric and electronic profile of the halogens influences biological activity and environmental persistence.

In materials science, halogenated aromatic carboxylic acids are used as ligands in metal–organic frameworks (MOFs) and coordination polymers, where the electron-withdrawing halogens tune the Lewis acidity of coordinated metal centers and influence pore environment properties.

Handling, Storage, and Safety Considerations

As with most halogenated aromatic carboxylic acids, 2-chloro-6-fluorobenzoic acid should be handled with appropriate personal protective equipment including nitrile gloves, safety glasses, and a laboratory coat. Work should be conducted in a well-ventilated area or fume hood to minimize inhalation of dust.

The compound should be stored in a tightly sealed container away from moisture, heat, and incompatible materials such as strong bases and oxidizing agents. Storage at room temperature in a cool, dry location is generally recommended to preserve purity over time.

Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for C124485 for authoritative hazard classification, first-aid measures, disposal procedures, and transport regulations before use. All waste should be disposed of in accordance with local environmental regulations governing halogenated organic compounds.

Ordering and Specifications

2-Chloro-6-fluorobenzoic acid is available from Aladdin Scientific under product code C124485. Researchers and procurement teams can obtain up-to-date information on available pack sizes, purity grades, current pricing, and stock availability by visiting the Aladdin Scientific website or contacting customer service.

When requesting a quotation, providing the SKU C124485, required quantity, and any specific purity or analytical certificate requirements will expedite the ordering process. Bulk quantities and custom packaging may be available upon request.

Aladdin Scientific is committed to supplying research-grade reagents with documented quality control data. Certificates of Analysis (CoA) are available for each lot to support compliance with laboratory quality management systems.

Frequently asked questions

What is the molecular weight of 2-Chloro-6-fluorobenzoic Acid?

The molecular weight of 2-Chloro-6-fluorobenzoic acid (C₇H₄ClFO₂) is 174.56 g/mol. This value is used when preparing molar solutions or calculating stoichiometry in synthesis reactions.

What makes 2-Chloro-6-fluorobenzoic Acid useful in pharmaceutical synthesis?

Its dual halogen substitution provides orthogonal reactivity: the aryl fluoride can participate in nucleophilic aromatic substitution (SNAr), while the aryl chloride is suitable for palladium-catalyzed cross-coupling reactions. The carboxylic acid group offers additional handles for amide, ester, or heterocycle formation, making it a versatile multi-functional building block for API synthesis.

How should 2-Chloro-6-fluorobenzoic Acid (C124485) be stored?

The compound should be stored in a tightly sealed container in a cool, dry place, away from moisture, strong bases, and oxidizing agents. Always refer to the Safety Data Sheet (SDS) available from Aladdin Scientific for the most authoritative storage and handling instructions specific to this product.

Can 2-Chloro-6-fluorobenzoic Acid undergo nucleophilic aromatic substitution?

Yes. Aryl fluorides are among the most reactive aryl halides in SNAr reactions due to fluorine's strong inductive electron-withdrawal, which stabilizes the Meisenheimer complex intermediate. The electron-withdrawing carboxylic acid group further activates the ring toward nucleophilic attack, particularly at positions bearing the fluorine substituent.

Where can I purchase 2-Chloro-6-fluorobenzoic Acid from Aladdin Scientific?

2-Chloro-6-fluorobenzoic acid is available directly from Aladdin Scientific under SKU C124485. Visit the Aladdin Scientific website to view current pack sizes, pricing, availability, and to place an order, or contact the customer service team for bulk inquiries.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley: New York, 1992. (General SNAr and cross-coupling reactivity of aryl halides.)
2. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; Wiley-Blackwell: Chichester, 2009. (Role of fluorine substituents in drug design.)
3. Aladdin Scientific product page for 2-Chloro-6-fluorobenzoic Acid, SKU C124485. https://www.aladdin-e.com

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.