4-Formyl-N-methylbenzamide: Properties, Uses & Lab Guide

4-Formyl-N-methylbenzamide is a bifunctional aromatic compound bearing both an aldehyde and an N-methylamide group on a para-substituted benzene ring, making it a valuable building block for diverse organic synthesis and medicinal chemistry applications.

Chemical Name

4-Formyl-N-methylbenzamide

SKU / Product Code

F724768

Functional Groups

Aldehyde (–CHO) and N-methylamide (–CONHMe) in para configuration

Molecular Formula

C9H9NO2

Molecular Weight

163.17 g/mol

Key Application

Intermediate in organic synthesis, medicinal chemistry, and heterocyclic chemistry

Storage Recommendation

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

Chemical Identity and Structure

4-Formyl-N-methylbenzamide (SKU: F724768) is a para-substituted benzene derivative carrying two distinct reactive functional groups: an aldehyde (–CHO) at the 4-position and an N-methylamide (–CONHMe) at the 1-position. Its molecular formula is C₉H₉NO₂, corresponding to a molecular weight of approximately 163.17 g/mol.

The coexistence of an electrophilic aldehyde carbon and a hydrogen-bond-donating/accepting amide group within the same rigid aromatic scaffold gives this compound exceptional versatility as a synthetic intermediate. The para geometry maximises the electronic and spatial separation of the two functional groups, enabling orthogonal reactivity in multi-step synthesis.

Physicochemical Properties and Stability

As an aromatic aldehyde-amide hybrid, 4-Formyl-N-methylbenzamide typically appears as a white to off-white crystalline solid at ambient conditions. The aldehyde group confers characteristic carbonyl absorption in the infrared spectrum (typically ~1680–1700 cm⁻¹ for aromatic aldehydes) and a distinctive singlet in the ¹H NMR spectrum near δ 10 ppm.

The compound is expected to be stable under standard laboratory conditions when stored properly. The aldehyde moiety, however, is susceptible to oxidation under prolonged exposure to air and moisture. Incompatibilities include strong oxidising agents, strong bases, and strong nucleophiles that may react with the aldehyde or amide functionality. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for authoritative physical constants and hazard data specific to this lot.

Research Applications and Synthetic Utility

The dual functionality of 4-Formyl-N-methylbenzamide makes it an attractive building block across several domains of chemical research:

• Medicinal Chemistry: The compound can serve as a precursor for the synthesis of bioactive molecules. The aldehyde group participates in reductive amination, condensation reactions, and Knoevenagel reactions, while the amide provides a pharmacophoric element commonly found in drug candidates.
• Heterocyclic Synthesis: Aromatic aldehydes are widely used in the preparation of heterocyclic scaffolds such as imidazoles, oxazoles, quinolines, and benzimidazoles. The pendant amide group can further direct or participate in ring-forming reactions.
• Imine and Hydrazone Formation: The aldehyde reacts readily with primary amines and hydrazines to form imines (Schiff bases) and hydrazones, respectively, which are useful intermediates in both synthesis and supramolecular chemistry.
• Materials and Polymer Chemistry: Bifunctional aromatic monomers are valuable in the construction of covalent organic frameworks (COFs), porous polymers, and functional materials.

These applications make F724768 relevant to academic research groups as well as pharmaceutical and materials science laboratories.

Handling, Storage, and Safety Guidelines

Good laboratory practice should be followed when handling 4-Formyl-N-methylbenzamide. Key recommendations include:

• Personal Protective Equipment (PPE): Wear appropriate gloves, safety glasses, and a laboratory coat. Use a fume hood when weighing or handling in open vessels to avoid inhalation of dust or vapours.
• Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated area, protected from light and heat sources. Keep away from strong oxidisers and reactive reagents.
• Disposal: Dispose of in accordance with local, regional, and national regulations governing chemical waste. Do not pour down the drain without prior verification of local regulations.
• First Aid: In case of skin or eye contact, flush with copious amounts of water and seek medical advice. If ingested or inhaled, follow the guidance in the current SDS.

Always refer to the most current Safety Data Sheet (SDS) supplied with the product or available from Aladdin Scientific for complete hazard and handling information specific to this reagent.

Ordering Information and Quality Assurance

4-Formyl-N-methylbenzamide is available from Aladdin Scientific under SKU F724768. Aladdin Scientific's reagents are manufactured and quality-controlled to meet the demands of modern research laboratories, with lot-specific analytical data available upon request.

For procurement enquiries, bulk pricing, or custom packaging requirements, please contact Aladdin Scientific's sales team. Researchers requiring certificates of analysis (CoA), safety data sheets (SDS), or additional technical support can access these documents through the Aladdin Scientific product portal or by contacting customer service directly.

Frequently asked questions

What are the main reactive sites in 4-Formyl-N-methylbenzamide?

The compound possesses two primary reactive sites: the aldehyde group (–CHO), which undergoes condensation, reductive amination, and oxidation reactions, and the N-methylamide group (–CONHMe), which can participate in hydrogen bonding and, under forcing conditions, in further derivatisation. The para arrangement of these groups allows for largely orthogonal reactivity in multistep synthesis.

How should 4-Formyl-N-methylbenzamide be stored to maintain stability?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated location, protected from direct light and sources of heat. Because the aldehyde functional group is susceptible to oxidation, exposure to air and moisture should be minimised. Refrigerated storage may be appropriate for long-term inventory; consult the product SDS or contact Aladdin Scientific for lot-specific recommendations.

In which types of chemical reactions is 4-Formyl-N-methylbenzamide commonly used?

This compound is commonly employed in Knoevenagel condensations, reductive amination, Schiff base formation, and heterocyclic ring synthesis (e.g., synthesis of imidazoles, benzimidazoles, or quinolines). The amide group can also serve as a pharmacophoric element or direct further functionalisation in medicinal chemistry programmes.

Is 4-Formyl-N-methylbenzamide suitable for use in medicinal chemistry?

Yes, its bifunctional aromatic architecture makes it a useful intermediate in medicinal chemistry. The aldehyde enables rapid library synthesis through condensation chemistry, while the N-methylamide is a motif frequently encountered in bioactive compounds. Researchers should verify purity specifications via the certificate of analysis before use in biological assays.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for aldehyde and amide reactivity.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level coverage of bifunctional aromatic building blocks.)
3. Aladdin Scientific. Product Page: 4-Formyl-N-methylbenzamide, SKU F724768. (Primary source for product identity and commercial availability.)

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