6-Fluoro-2,3-dimethoxybenzaldehyde: Properties & Applications

6-Fluoro-2,3-dimethoxybenzaldehyde is a fluorine-substituted aromatic aldehyde bearing two methoxy groups at the 2- and 3-positions, making it a valuable building block in medicinal chemistry and organic synthesis.

CAS Number

Needs verification — not provided in source material

Molecular Formula

C9H9FO3

Molecular Weight

Approximately 184.16 g/mol (needs verification)

Key Functional Groups

Aldehyde (–CHO), two methoxy groups (–OCH3), one fluorine substituent

Appearance

Typically a solid or crystalline material (needs verification)

Primary Use

Pharmaceutical intermediate and organic synthesis building block

Chemical Structure and Properties

6-Fluoro-2,3-dimethoxybenzaldehyde is an aromatic aldehyde characterized by a benzene ring bearing a fluorine atom at the 6-position, methoxy groups at the 2- and 3-positions, and an aldehyde group at the 1-position. This combination of electron-donating methoxy substituents and an electron-withdrawing fluorine atom creates a unique electronic environment on the aromatic ring.

The aldehyde functionality renders the compound highly reactive toward nucleophilic addition reactions, while the fluorine substituent modulates both the electronic density of the ring and the acidity of the aldehyde carbon. The two methoxy groups donate electron density through resonance, influencing regioselectivity in electrophilic aromatic substitution reactions. Together, these features make 6-Fluoro-2,3-dimethoxybenzaldehyde a structurally differentiated reagent with tunable reactivity for diverse synthetic applications.

Synthesis and Handling Considerations

As a functionalized benzaldehyde, 6-Fluoro-2,3-dimethoxybenzaldehyde should be stored under appropriate conditions to prevent degradation of the aldehyde moiety. General best practices for aromatic aldehydes include storage in a cool, dry, well-ventilated location away from strong oxidizers and bases, in a tightly sealed container to minimize air and moisture exposure.

When handling this compound in the laboratory, standard personal protective equipment (PPE) is recommended, including lab coat, nitrile gloves, and safety glasses. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for specific hazard classifications, first-aid measures, and disposal guidelines before use. All manipulations should be carried out in a fume hood when working with volatile quantities or in powder form.

Applications in Organic and Medicinal Chemistry

6-Fluoro-2,3-dimethoxybenzaldehyde serves as a versatile intermediate in the synthesis of complex organic molecules. The aldehyde group can participate in a broad range of transformations including condensation reactions (e.g., Knoevenagel, Wittig, and reductive amination), cyclization reactions, and as a precursor to alcohols, carboxylic acids, and imines.

The incorporation of a fluorine atom is particularly valued in medicinal chemistry, as fluorine substitution on drug candidates can enhance metabolic stability, improve membrane permeability, and modulate binding affinity to biological targets. Compounds derived from fluorinated benzaldehyde scaffolds have been explored in the development of CNS-active agents, antimicrobials, and enzyme inhibitors. The methoxy groups additionally provide handles for further functionalization via demethylation to free phenols or through directed ortho-metalation strategies.

Purity, Specifications, and Quality

Aladdin Scientific supplies 6-Fluoro-2,3-dimethoxybenzaldehyde (SKU: F724990) to support demanding research and synthetic workflows. For sensitive synthetic applications, reagent purity is a critical parameter, as trace impurities in aldehyde reagents can affect reaction yields, selectivity, and reproducibility.

Researchers and procurement teams are encouraged to request the Certificate of Analysis (CoA) for the specific lot number to confirm purity by methods such as GC or HPLC, confirm identity by NMR or mass spectrometry data, and verify water content by Karl Fischer titration where applicable. Specific purity grades and available pack sizes should be confirmed directly with Aladdin Scientific product listings or customer service.

Frequently asked questions

What is 6-Fluoro-2,3-dimethoxybenzaldehyde used for in research?

6-Fluoro-2,3-dimethoxybenzaldehyde is primarily used as a building block in organic and medicinal chemistry. Its aldehyde group enables condensation, reductive amination, and cyclization reactions, while the fluorine substituent imparts properties valuable for pharmaceutical lead optimization, such as improved metabolic stability and modulated binding affinity.

How should 6-Fluoro-2,3-dimethoxybenzaldehyde be stored to maintain stability?

This compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from oxidizing agents, strong bases, and moisture. Researchers should consult the Aladdin Scientific Safety Data Sheet for lot-specific storage temperature recommendations and shelf-life information.

What is the molecular formula of 6-Fluoro-2,3-dimethoxybenzaldehyde?

The molecular formula of 6-Fluoro-2,3-dimethoxybenzaldehyde is C9H9FO3, corresponding to a molecular weight of approximately 184.16 g/mol. Researchers should verify these values against the Certificate of Analysis provided with each lot.

Why is the fluorine substituent important in this benzaldehyde derivative?

Fluorine is a bioisostere frequently used in medicinal chemistry to improve drug-like properties. In 6-Fluoro-2,3-dimethoxybenzaldehyde, the fluorine atom modulates the electronic character of the aromatic ring, can improve the metabolic stability of derived compounds, and may enhance their interaction with biological targets, making this scaffold attractive for pharmaceutical research.

Where can I purchase 6-Fluoro-2,3-dimethoxybenzaldehyde from Aladdin Scientific?

6-Fluoro-2,3-dimethoxybenzaldehyde is available from Aladdin Scientific under SKU F724990. Researchers and procurement teams can place orders through the Aladdin Scientific website or by contacting customer service for pricing, available pack sizes, and delivery information.

References

1. General reference: Fluorine in medicinal chemistry — textbook-level knowledge on fluorine substitution effects in drug design. Specific citations require verification.
2. General reference: March's Advanced Organic Chemistry — reactions of aromatic aldehydes including condensation, reductive amination, and nucleophilic addition. Specific edition and page numbers require verification.

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