6-Fluoro-4-oxo-4H-chromene-3-carboxylic Acid: Lab Handling Guide
6-Fluoro-4-oxo-4H-chromene-3-carboxylic Acid: Lab Handling Guide
6-Fluoro-4-oxo-4H-chromene-3-carboxylicacid is a fluorinated chromone-derived building block widely employed in medicinal chemistry and heterocyclic synthesis as a versatile scaffold for drug discovery programs.
- Chemical Name
- 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid
- SKU
- F709030
- Core Scaffold
- 4H-chromene (chromone) fused bicyclic ring system
- Key Functional Groups
- Carboxylic acid (C-3), ketone (C-4), fluorine substituent (C-6)
- Typical Application
- Synthetic intermediate and building block for heterocyclic drug candidates
- Recommended Storage
- Cool, dry, well-ventilated area; sealed container away from moisture and light
Chemical Identity and Structural Features
6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid belongs to the chromone (4H-chromen-4-one) family of oxygen-containing heterocycles. The parent chromone bicyclic framework consists of a benzene ring fused to a γ-pyrone ring. In this compound, three key modifications define its reactivity and utility:
- C-6 Fluorine substitution: The electron-withdrawing fluorine atom on the benzene ring modulates the electronic density of the aromatic system, influencing lipophilicity, metabolic stability, and binding interactions in biological targets — properties highly valued in lead optimization.
- C-4 Ketone (oxo group): The γ-pyrone carbonyl contributes to the conjugated π-system and can participate in hydrogen-bond-acceptor interactions.
- C-3 Carboxylic acid: This free carboxylic acid functionality provides a handle for amide coupling, esterification, and other classical transformations, making the compound a versatile synthetic intermediate.
The combination of these features makes 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid a privileged building block in medicinal chemistry, particularly for the construction of chromone-based libraries.
Applications in Synthesis and Drug Discovery
The chromone scaffold is a recurring motif in natural products and pharmacologically active molecules. The C-3 carboxylic acid of 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid enables a variety of downstream transformations:
- Amide bond formation: Coupling with primary or secondary amines using standard peptide-coupling reagents (e.g., EDC/HOBt, HATU) furnishes chromone-3-carboxamides, a class of compounds explored for kinase inhibition and anti-inflammatory activity.
- Esterification: Reaction with alcohols under acid catalysis or via acyl chloride intermediates yields ester prodrug candidates or further-functionalized analogs.
- Cyclocondensation: The activated carbonyl/carboxylic acid combination can serve as a dipolarophile or electrophilic partner in multicomponent reactions to assemble polycyclic frameworks.
- Coordination chemistry: Chromone carboxylic acids have been explored as ligands for metal-organic frameworks (MOFs) and coordination polymers due to their bifunctional donor capacity.
The fluorine atom at C-6 additionally provides a useful 19F NMR spectroscopic handle for reaction monitoring and binding studies.
Handling, Storage, and Safety Guidelines
Although specific GHS hazard classification data for 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid (SKU F709030) should be confirmed in the product Safety Data Sheet (SDS), general best-practice guidelines for handling fine organic reagents of this class apply:
- Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves (e.g., nitrile), safety goggles, and a laboratory coat. Work in a fume hood when handling powdered material to avoid inhalation of dust.
- Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the label), dry location away from direct light, moisture, and incompatible materials (strong oxidizers, strong bases).
- Stability: As a carboxylic acid, the compound may be sensitive to moisture over extended periods. Desiccant storage is recommended for long-term inventory.
- Disposal: Dispose of in accordance with local, regional, and national regulations for organic chemical waste. Do not pour down the drain without proper treatment.
- First Aid: In case of skin or eye contact, rinse with copious water. Consult the SDS for full emergency procedures.
Always consult the current product SDS (available from Aladdin Scientific) before use.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid under SKU F709030. Researchers and procurement teams should note the following when ordering:
- Purity: Specific purity grades and analytical certificates (COA) are available upon request or via the product page. Confirm purity by HPLC or NMR as appropriate for your application.
- Quantity: The compound is available in research quantities; contact Aladdin Scientific for bulk pricing and custom pack sizes.
- Lot-to-lot consistency: Request Certificate of Analysis for each lot to verify identity (e.g., 1H NMR, 13C NMR, 19F NMR, MS) and purity before use in sensitive assays.
- Lead time and shipping: Standard shipping conditions apply; consult current product listing for availability and estimated dispatch times.
For technical questions regarding this product, contact Aladdin Scientific technical support.
Frequently asked questions
What is 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid used for in research?
It is primarily used as a heterocyclic building block in medicinal chemistry and synthetic organic chemistry. The C-3 carboxylic acid enables amide coupling, esterification, and other reactions to generate chromone-based analogs for biological screening, including exploration of kinase inhibition and anti-inflammatory targets.
How should 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid (F709030) be stored to maintain stability?
Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, protected from direct light and moisture. For long-term storage, use a desiccant to prevent hydration of the carboxylic acid moiety. Always refer to the product SDS and COA for lot-specific guidance.
What role does the fluorine substituent play in 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid?
The C-6 fluorine atom is an electron-withdrawing group that modulates the electronic properties and lipophilicity of the chromone scaffold. In drug discovery, fluorine substitution is frequently introduced to improve metabolic stability, enhance membrane permeability, and fine-tune binding affinity to biological targets. It also provides a convenient 19F NMR spectroscopic handle for reaction monitoring.
How can I confirm the identity and purity of the received batch of F709030?
Request the Certificate of Analysis (COA) from Aladdin Scientific for your specific lot. Identity can be confirmed by 1H NMR, 13C NMR, 19F NMR, and high-resolution mass spectrometry. Purity is typically assessed by HPLC with UV detection. Contact Aladdin Scientific technical support if analytical data are required.
References
- General reference: Chromone scaffold in medicinal chemistry — textbook-level knowledge on chromone-based building blocks and their applications in drug discovery.
- General reference: Role of fluorine in medicinal chemistry — textbook-level knowledge on fluorine substituent effects on lipophilicity, metabolic stability, and binding affinity.
- Aladdin Scientific product listing for 6-Fluoro-4-oxo-4H-chromene-3-carboxylic acid, SKU F709030. 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）