4-(3-Fluorobenzyloxy)benzaldehyde: Properties & Lab Use

4-(3-Fluorobenzyloxy)benzaldehyde is a fluorine-containing aromatic aldehyde widely employed as a versatile building block in organic synthesis and medicinal chemistry research.

Chemical Name

4-(3-Fluorobenzyloxy)benzaldehyde

SKU

F140223

Molecular Formula

C14H11FO2

Molecular Weight

230.23 g/mol

Functional Groups

Aldehyde (–CHO), aryl ether (–O–), aryl fluoride (Ar–F)

Appearance

White to off-white solid or pale yellow oil (verify with CoA)

What Is 4-(3-Fluorobenzyloxy)benzaldehyde and What Is Its Structure?

4-(3-Fluorobenzyloxy)benzaldehyde (SKU F140223) is an aromatic aldehyde consisting of a 4-formylphenyl (para-hydroxybenzaldehyde-derived) core connected via a benzyl ether linkage to a 3-fluorobenzyl group. The molecule incorporates three key functional handles: an electrophilic aldehyde carbonyl suitable for condensation and nucleophilic addition reactions, an aryl ether oxygen that confers moderate lipophilicity, and a meta-fluorine substituent on the pendant benzyl ring that modulates electronic properties and metabolic stability in drug-like molecules.

Its molecular formula is C₁₄H₁₁FO₂ with a molecular weight of approximately 230.23 g/mol. The compound belongs to the broader class of fluorinated benzyloxybenzaldehyde derivatives frequently used as synthetic intermediates.

Key Applications in Organic Synthesis and Drug Discovery

The aldehyde group in 4-(3-Fluorobenzyloxy)benzaldehyde makes it a highly reactive handle for a wide range of synthetic transformations. Researchers routinely employ it in:

• Reductive amination to produce secondary amines bearing the fluorobenzyloxyphenyl pharmacophore.
• Knoevenagel condensations and Wittig/Horner–Wadsworth–Emmons reactions to build extended π-conjugated systems.
• Schiff base (imine) formation with primary amines, giving intermediates for further reduction or cyclization.
• Heterocyclic synthesis, for example in the preparation of oxazoles, imidazoles, and benzimidazoles where the aldehyde acts as a C1 building block.

The meta-fluoro substitution pattern is particularly valued in medicinal chemistry because fluorine can improve metabolic stability, membrane permeability, and binding selectivity, making this compound a popular scaffold in hit-to-lead optimization campaigns.

Handling, Storage, and Safety Considerations

Although 4-(3-Fluorobenzyloxy)benzaldehyde is not classified among highly acutely toxic reagents, standard precautions for aromatic aldehydes should be observed:

• Personal protective equipment (PPE): Wear nitrile gloves, safety glasses, and a lab coat. Use a fume hood when weighing or handling open containers.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from strong oxidizers and bases. Refrigeration (2–8 °C) is recommended for long-term stability; check the product Certificate of Analysis (CoA) for the specific recommended storage condition.
• Stability: Aromatic aldehydes can be susceptible to aerial oxidation over extended periods. Purging storage containers with inert gas (N₂ or Ar) before resealing is advisable for opened material.
• Disposal: Follow all local and institutional regulations for disposal of halogenated organic compounds.

Always consult the Safety Data Sheet (SDS) supplied with the product for complete hazard information before use.

Purity, Grade, and Quality Specifications

Aladdin Scientific supplies 4-(3-Fluorobenzyloxy)benzaldehyde (F140223) for research use. Purity specifications and analytical data—including HPLC purity, NMR confirmation of structure, and water content where applicable—are documented on the Certificate of Analysis (CoA) specific to each production lot. Researchers are encouraged to:

• Download and review the lot-specific CoA from the Aladdin Scientific product page before use.
• Confirm purity requirements align with the intended application; for demanding asymmetric catalysis or biological assays, additional in-house characterization (e.g., GC, LC-MS) may be warranted.
• Contact Aladdin Scientific technical support if custom purity grades or bulk quantities are required.

Standard research-grade material is typically supplied at ≥97% purity (by HPLC or GC); verify the exact figure on the current lot CoA, as specifications may vary.

Ordering and Availability

4-(3-Fluorobenzyloxy)benzaldehyde is available from Aladdin Scientific under SKU F140223. To place an order:

• Search for F140223 on the Aladdin Scientific website and add the desired pack size to your cart.
• Academic and institutional purchase orders are accepted; contact the Aladdin Scientific sales team for volume pricing or framework agreements.
• For questions about lead times, export documentation, or certificate requirements, contact Aladdin Scientific customer service directly.

Availability and pack sizes are subject to change; please verify current stock status on the product page at the time of ordering.

Frequently asked questions

What is the molecular weight and formula of 4-(3-Fluorobenzyloxy)benzaldehyde?

The molecular formula of 4-(3-Fluorobenzyloxy)benzaldehyde is C14H11FO2, corresponding to a molecular weight of approximately 230.23 g/mol. Always verify exact values against the lot-specific Certificate of Analysis provided by Aladdin Scientific.

How should 4-(3-Fluorobenzyloxy)benzaldehyde be stored to maintain its stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from strong oxidizing agents and bases. Cold storage at 2–8 °C is recommended for long-term preservation. After opening, purge the container with inert gas (nitrogen or argon) before resealing to minimize oxidation of the aldehyde functionality.

In what types of chemical reactions is 4-(3-Fluorobenzyloxy)benzaldehyde commonly used?

This compound is routinely used in reductive aminations, Knoevenagel condensations, Wittig and Horner–Wadsworth–Emmons olefination reactions, Schiff base formations, and heterocyclic ring synthesis. Its reactive aldehyde group makes it a versatile C1 building block, while the meta-fluorobenzyl ether moiety contributes pharmacophoric properties valued in medicinal chemistry programs.

What purity level is supplied for Aladdin Scientific product F140223?

Standard research-grade 4-(3-Fluorobenzyloxy)benzaldehyde (F140223) is typically supplied at ≥97% purity as determined by HPLC or GC. The precise purity value for your specific lot is documented on the Certificate of Analysis available on the Aladdin Scientific product page. Contact technical support if a higher purity grade is required.

Why is the meta-fluoro substitution pattern important in this compound?

The meta-fluorine atom influences both the electronic character of the benzyl ring and the overall lipophilicity of the molecule. In drug discovery, fluorine substitution at the meta position is frequently exploited to improve metabolic stability against cytochrome P450 oxidation, enhance membrane permeability, and fine-tune receptor binding affinity—making this compound a strategic choice for scaffold decoration in lead optimization.

References

1. Aladdin Scientific product page: 4-(3-Fluorobenzyloxy)benzaldehyde, SKU F140223. Certificate of Analysis and Safety Data Sheet available on request.
2. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Fluorine in medicinal chemistry. Chem. Soc. Rev. 2008, 37, 320–330. doi:10.1039/b610213c
3. O'Hagan, D. Understanding organofluorine chemistry. An introduction to the C–F bond. Chem. Soc. Rev. 2008, 37, 308–319. doi:10.1039/b711844a

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