What Is 4-Formyl-N-methylbenzamide?

4-Formyl-N-methylbenzamide is a para-disubstituted aromatic compound that combines two synthetically important functional groups on a single benzene scaffold: a reactive aldehyde (–CHO) at the 4-position and an N-methyl amide (–CONHCH₃) at the 1-position. This combination makes the molecule a bifunctional building block suitable for constructing more complex molecular architectures through selective reaction at either or both functional groups.

The aldehyde moiety can participate in condensation reactions, reductive aminations, Wittig olefinations, and imine formations, while the amide group can serve as a hydrogen-bond donor/acceptor or be further elaborated. The N-methyl substitution on the amide nitrogen reduces hydrogen-bond donation capacity relative to a primary amide, which can be exploited in drug-design contexts to modulate membrane permeability and metabolic stability of derived compounds.

Key Chemical Properties and Handling

As an aromatic aldehyde, 4-Formyl-N-methylbenzamide is susceptible to oxidation under prolonged exposure to air and light, which can lead to formation of the corresponding carboxylic acid. To preserve reagent integrity, it is recommended to store the compound under inert atmosphere (nitrogen or argon) in a tightly sealed container, in a cool and dry location away from strong oxidizing agents.

The compound is a solid at room temperature. Standard laboratory personal protective equipment (PPE) — including gloves, safety glasses, and a laboratory coat — should be worn when handling the material. Users should consult the Safety Data Sheet (SDS) provided with the product for comprehensive hazard information, first-aid measures, and disposal guidance, as detailed toxicological data specific to this compound may be limited in the open literature.

Common Research and Synthetic Applications

4-Formyl-N-methylbenzamide serves primarily as an intermediate in medicinal chemistry and pharmaceutical research programs. Its aldehyde group enables rapid library synthesis through:

• Reductive amination — coupling with primary or secondary amines in the presence of a reducing agent to introduce nitrogen-containing side chains.
• Condensation reactions — forming Schiff bases (imines) or hydrazones with amine nucleophiles, useful for fragment-based drug discovery and probe development.
• Heterocycle synthesis — serving as a precursor to benzimidazoles, oxazoles, and related nitrogen/oxygen heterocycles when reacted with bifunctional nucleophiles.

The pre-installed N-methylamide group can simultaneously act as a pharmacophore element or a handle for further structural diversification, making this compound particularly attractive for parallel synthesis workflows.

Ordering and Availability from Aladdin Scientific

4-Formyl-N-methylbenzamide is available from Aladdin Scientific under SKU F724768. Researchers and procurement teams can obtain current pricing, available pack sizes, purity specifications, and stock status directly through the Aladdin Scientific website or by contacting customer service.

When placing an order, it is recommended to verify the Certificate of Analysis (CoA) for lot-specific purity data (typically reported by HPLC and/or NMR). If a specific purity grade or custom quantity is required for GMP-adjacent or regulated research workflows, please contact Aladdin Scientific technical support to discuss available options.