6-Fluoro-2,3-dimethoxybenzaldehyde: Properties & Lab Use Guide

6-Fluoro-2,3-dimethoxybenzaldehyde is a fluorine-substituted aromatic aldehyde bearing two methoxy groups at the 2- and 3-positions, widely employed as a versatile building block in pharmaceutical synthesis and fine-chemical research.

CAS-style Molecular Formula

C9H9FO3

Molecular Weight

184.16 g/mol (calculated)

Functional Groups

Aldehyde (–CHO), fluoro (–F), two methoxy (–OCH3)

Key Application

Pharmaceutical intermediate and fine-chemical synthesis building block

Aladdin SKU

F724990

Storage Recommendation

Store in a cool, dry, well-ventilated area away from light and moisture

Chemical Identity and Structure

6-Fluoro-2,3-dimethoxybenzaldehyde is an aromatic aldehyde derived from the benzaldehyde scaffold with three substituents on the ring: a fluorine atom at the 6-position, and methoxy groups at the 2- and 3-positions. This substitution pattern creates an electron-rich aromatic ring modulated by the electron-withdrawing inductive effect of fluorine, producing a compound with a distinctive balance of nucleophilic and electrophilic reactivity.

The aldehyde carbonyl (–CHO) is the primary reactive site, making the compound amenable to a wide range of transformations including condensation reactions, reductive amination, Wittig olefination, and nucleophilic addition. The fluorine substituent enhances metabolic stability and lipophilicity in derived drug candidates, a property highly valued in medicinal chemistry programs.

Handling, Safety, and Storage Guidelines

Personal Protective Equipment (PPE): When handling 6-Fluoro-2,3-dimethoxybenzaldehyde, wear appropriate chemical-resistant gloves (e.g., nitrile), safety goggles, and a laboratory coat. Work in a fume hood to avoid inhalation of dust or vapors from the aldehyde functional group.

Storage: Store the compound in a tightly sealed container in a cool (2–8 °C or as specified on the product label), dry, and well-ventilated area, away from direct light, oxidizing agents, and incompatible materials. Moisture ingress should be minimized to prevent potential hydration of the aldehyde functionality.

Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing aromatic aldehydes and fluorinated organic compounds. Consult your institution's Environmental Health and Safety (EHS) office for specific disposal protocols.

Note: Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use. Specific hazard classifications and first-aid measures are detailed in the SDS for SKU F724990.

Synthetic Applications and Research Uses

6-Fluoro-2,3-dimethoxybenzaldehyde serves as a key building block in the synthesis of a range of biologically active molecules and pharmaceutical intermediates. The aldehyde group enables direct coupling with amines (reductive amination), hydrazines (hydrazone formation), and active methylene compounds (Knoevenagel condensation), providing rapid access to structurally diverse libraries for drug discovery.

The fluorine atom at the 6-position is particularly valuable for medicinal chemists because C–F bonds are metabolically resistant, can modulate pKa values of adjacent functional groups, and improve membrane permeability of derived compounds. The two methoxy groups introduce steric and electronic diversity, influencing binding affinity to biological targets.

Typical synthetic workflows employing this aldehyde include: (1) formation of Schiff bases with primary amines for antimicrobial or anticancer lead identification; (2) use as an electrophilic partner in palladium-catalyzed cross-coupling after appropriate derivatization; and (3) incorporation into heterocyclic ring-forming sequences to access fluorinated benzimidazoles, oxazoles, or related scaffolds commonly found in approved drugs.

Quality, Purity, and Analytical Verification

For reliable research outcomes, the purity of 6-Fluoro-2,3-dimethoxybenzaldehyde must be rigorously verified prior to use. Aladdin Scientific supplies this compound (SKU F724990) with a defined purity specification; researchers should consult the current Certificate of Analysis (CoA) for the specific lot purchased.

Common analytical techniques for identity and purity confirmation include:

• 1H and 13C NMR spectroscopy: Confirms regiochemistry of fluoro and methoxy substituents, and aldehyde proton signal near δ 10 ppm.
• 19F NMR spectroscopy: Provides unambiguous confirmation of the fluorine substituent and its chemical environment.
• GC or HPLC purity analysis: Quantifies the area percentage of the target compound versus impurities.
• Mass spectrometry (MS): Confirms molecular ion at m/z 184 consistent with C9H9FO3.

Researchers undertaking sensitive biological assays or asymmetric synthesis should verify purity independently and consider recrystallization or column chromatography if the application demands material of higher purity than the supplied specification.

Frequently asked questions

What is the recommended storage temperature for 6-Fluoro-2,3-dimethoxybenzaldehyde (F724990)?

The compound should be stored in a cool, dry, and well-ventilated location, away from light and moisture. Typically 2–8 °C is recommended for long-term stability of aldehyde-containing compounds; however, always refer to the specific storage conditions stated on the Aladdin Scientific product label and Certificate of Analysis for lot F724990.

Which reactions can 6-Fluoro-2,3-dimethoxybenzaldehyde participate in as a synthetic building block?

The aldehyde functionality makes this compound suitable for reductive amination, Knoevenagel condensation, Wittig olefination, Schiff base formation with primary amines, and nucleophilic addition reactions. The fluorine substituent also allows access to further functionalization strategies relevant in medicinal chemistry.

How should I confirm the identity and purity of F724990 before use in a sensitive assay?

Identity can be confirmed by 1H, 13C, and 19F NMR spectroscopy and mass spectrometry (expected m/z 184 for C9H9FO3). Purity should be assessed by GC or HPLC and cross-referenced with the Certificate of Analysis provided by Aladdin Scientific for the specific lot. If higher purity is required, recrystallization or column chromatography may be employed.

Is 6-Fluoro-2,3-dimethoxybenzaldehyde suitable for use in biological screening assays?

It can serve as a starting material or intermediate for the preparation of biologically active compounds used in screening. However, researchers should verify purity, solubility in the assay medium (e.g., DMSO), and ensure compatibility with the biological system before proceeding, as aldehydes can react non-specifically with nucleophilic residues in proteins.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General aldehyde reactivity reference)
2. Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine. Wiley-VCH, 2008. (Fluorine in medicinal chemistry)
3. Aladdin Scientific. Certificate of Analysis, 6-Fluoro-2,3-dimethoxybenzaldehyde, SKU F724990. (Internal lot-specific document; contact Aladdin for current CoA)

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