4,5-Dichloro-2-methoxybenzoic Acid: Properties & Lab Use

4，5-Dichloro-2-methoxybenzoic acid is a halogenated aromatic carboxylic acid bearing two chloro substituents and a methoxy group on the benzene ring, making it a versatile building block in pharmaceutical synthesis, agrochemical research, and chemical biology studies.

IUPAC Name

4,5-Dichloro-2-methoxybenzoic acid

SKU

D691474

Molecular Formula

C8H6Cl2O3

Molecular Weight

221.04 g/mol

Functional Groups

Carboxylic acid (–COOH), methoxy (–OCH3), two aryl chlorides

Supplier SKU Source

Aladdin Scientific – D691474

Chemical Identity and Structure

4,5-Dichloro-2-methoxybenzoic acid (CAS number to be confirmed; see review flags) is a substituted benzoic acid in which chlorine atoms occupy the 4- and 5-positions of the aromatic ring and a methoxy (–OCH₃) group is located at the 2-position, ortho to the carboxylic acid functionality. Its molecular formula is C₈H₆Cl₂O₃, corresponding to a molecular weight of approximately 221.04 g/mol.

The electron-withdrawing nature of the two chloro substituents significantly lowers the pKa of the carboxylic acid relative to unsubstituted benzoic acid, while the ortho methoxy group introduces steric and electronic effects that influence reactivity in condensation and coupling reactions. This combination of substituents defines the compound's reactivity profile and makes it distinguishable from related mono-chlorinated or unsubstituted analogs.

Research and Synthetic Applications

Halogenated methoxybenzoic acids such as 4,5-dichloro-2-methoxybenzoic acid serve as important intermediates in the synthesis of pharmaceuticals, agrochemicals, and specialty materials. The aryl chloride moieties provide handles for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig), while the carboxylic acid group enables amide bond formation, esterification, and Curtius rearrangement to generate amine-containing products.

In medicinal chemistry, halogenated benzoic acid scaffolds are frequently incorporated into drug candidates targeting enzyme active sites, where the electron-deficient aromatic ring can participate in halogen bonding or pi-stacking interactions with protein residues. The methoxy group may additionally confer metabolic stability or modulate binding affinity. Researchers working on herbicide or fungicide development may also find this compound relevant as a lead structure or synthetic precursor.

Handling, Storage, and Safety Considerations

As with most halogenated aromatic carboxylic acids, 4,5-dichloro-2-methoxybenzoic acid should be handled with appropriate personal protective equipment, including nitrile gloves, safety glasses, and a laboratory coat. Operations that may generate dust or aerosols should be conducted in a well-ventilated fume hood.

The compound should be stored in a tightly sealed container away from moisture, strong oxidizers, and strong bases. Recommended storage is at room temperature in a cool, dry location unless specific temperature requirements are indicated on the product certificate of analysis. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for authoritative hazard classifications, first-aid measures, and disposal guidance prior to use.

Ordering and Quality Information

4,5-Dichloro-2-methoxybenzoic acid is available from Aladdin Scientific under SKU D691474. Prospective purchasers should request a certificate of analysis (CoA) confirming purity, identity (confirmed by NMR or HPLC), and lot-specific quality data before use in critical assays or synthesis campaigns.

For bulk quantities, custom packaging, or specific purity grades required for GMP-adjacent workflows, laboratory managers and procurement teams are encouraged to contact Aladdin Scientific's technical sales team directly. Volume pricing and reagent qualification support may be available depending on project requirements.

Frequently asked questions

What reactions can 4,5-dichloro-2-methoxybenzoic acid participate in?

This compound can undergo transition-metal-catalyzed cross-coupling reactions at the aryl chloride positions (e.g., Suzuki, Buchwald–Hartwig), amide bond formation or esterification via the carboxylic acid group, and electrophilic or nucleophilic aromatic substitution under appropriate conditions. The ortho methoxy group may sterically influence selectivity in some transformations.

How should I store 4,5-dichloro-2-methoxybenzoic acid (D691474)?

Store the compound in a tightly sealed container in a cool, dry place away from moisture, strong oxidizers, and strong bases. Always consult the Aladdin Scientific Safety Data Sheet (SDS) and the lot-specific certificate of analysis for confirmed storage conditions.

Is 4,5-dichloro-2-methoxybenzoic acid suitable for pharmaceutical intermediate applications?

Yes, halogenated methoxybenzoic acid scaffolds are widely used in medicinal chemistry as intermediates for building drug candidates. Researchers should verify the purity grade and obtain a certificate of analysis from Aladdin Scientific (SKU D691474) to ensure suitability for their specific synthetic or biological application.

What is the molecular weight of 4,5-dichloro-2-methoxybenzoic acid?

The molecular formula of 4,5-dichloro-2-methoxybenzoic acid is C8H6Cl2O3, giving a calculated molecular weight of approximately 221.04 g/mol. Researchers should confirm this value against the lot-specific certificate of analysis provided with the product.

References

1. Aladdin Scientific product listing: 4,5-Dichloro-2-methoxybenzoic acid, SKU D691474.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, general reference for aromatic substitution and carboxylic acid reactivity.
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press; reference for halogenated aromatic compound reactivity.

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