3-[(Dimethylamino)methyl]benzaldehyde: Properties & Lab Use

3-[(Dimethylamino)methyl]benzaldehyde is a bifunctional aromatic compound bearing both a reactive aldehyde group and a tertiary amine moiety on the meta-substituted benzene ring, making it a versatile intermediate in organic synthesis and medicinal chemistry research.

Product SKU

B728005

IUPAC Name

3-[(dimethylamino)methyl]benzaldehyde

Functional Groups

Aldehyde (–CHO) and tertiary amine (–N(CH3)2)

Substitution Pattern

Meta (1,3) substitution on benzene ring

Primary Research Use

Organic synthesis intermediate, Mannich-type reactions, medicinal chemistry building block

Storage Recommendation

Store in a cool, dry, well-ventilated area away from heat and incompatible materials; verify exact conditions on SDS

What Is 3-[(Dimethylamino)methyl]benzaldehyde?

3-[(Dimethylamino)methyl]benzaldehyde (Aladdin SKU: B728005) is an aromatic organic compound that combines two key reactive functionalities on a single benzene scaffold: a formyl group (–CHO) at the 1-position and a dimethylaminomethyl group (–CH₂N(CH₃)₂) at the 3-position (meta). This combination classifies it as both an aromatic aldehyde and a Mannich base derivative.

The aldehyde group readily participates in condensation reactions, reductive amination, imine formation, and Wittig-type chemistry, while the tertiary amine offers additional handles for quaternization, coordination chemistry, or pH-responsive behavior. Together, these features make 3-[(dimethylamino)methyl]benzaldehyde a valuable bifunctional building block in complex molecule assembly.

Key Chemical Properties and Handling

As an aromatic aldehyde, 3-[(dimethylamino)methyl]benzaldehyde is susceptible to oxidation; prolonged exposure to air can lead to partial conversion to the corresponding carboxylic acid. Researchers should store the compound under inert atmosphere or in tightly sealed containers where possible, following the specific guidance provided in the Safety Data Sheet (SDS) supplied with SKU B728005.

The tertiary amine nitrogen may act as a mild base and can form salts with acids, which is sometimes exploited during purification steps. Standard laboratory precautions for handling reactive aldehydes apply: use appropriate personal protective equipment (PPE) including gloves, safety goggles, and lab coat; work in a fume hood; and avoid contact with strong oxidizing agents, strong acids, and strong bases.

Precise physicochemical data (molecular weight, melting point, boiling point, density, and purity specifications) should be confirmed from the product Certificate of Analysis (CoA) and SDS provided by Aladdin Scientific at the time of purchase.

Research and Synthetic Applications

The dual functionality of 3-[(dimethylamino)methyl]benzaldehyde makes it attractive across several research domains:

• Medicinal chemistry: It serves as a building block for the synthesis of pharmacologically active compounds, particularly where a meta-substituted aromatic core bearing both an aldehyde electrophile and an amine nucleophile/donor is required.
• Mannich-type chemistry: As a preformed Mannich base, it can be employed directly in reactions with nucleophiles, bypassing the need for in situ Mannich condensation with formaldehyde and a secondary amine.
• Schiff base and imine formation: The aldehyde reacts readily with primary amines to form imines (Schiff bases), which are useful intermediates in asymmetric catalysis, ligand design, and bioconjugation.
• Fluorescent probe and sensor development: Bifunctional aminomethyl-benzaldehyde scaffolds have been explored in the construction of fluorescent probes and metal-ion sensors, leveraging both coordinating and chromophoric moieties.

Researchers should design reaction conditions based on the specific transformation intended, verifying reagent compatibility and yield optimization in their own laboratory context.

Ordering, Purity, and Quality Assurance

3-[(Dimethylamino)methyl]benzaldehyde is available from Aladdin Scientific under SKU B728005. When placing an order, researchers and procurement teams should confirm:

• Purity grade: Check the current CoA for lot-specific purity data (typically reported as % purity by GC or HPLC). If a specific purity threshold is required for a sensitive assay, contact Aladdin Scientific technical support before ordering.
• Pack sizes and pricing: Available pack sizes and current pricing are listed on the product page. Volume discounts may be available; contact the sales team for quotations on bulk quantities.
• Lead time: Availability and lead times may vary by region. Confirm stock status on the Aladdin Scientific website or through your regional representative.
• Documentation: CoA, SDS, and structural confirmation data (e.g., NMR, MS) are available upon request or via the product page download center.

For technical questions regarding application suitability or reagent compatibility, Aladdin Scientific's technical support team is available to assist prior to purchase.

Frequently asked questions

What are the two main functional groups in 3-[(Dimethylamino)methyl]benzaldehyde and why do they matter?

The compound contains an aromatic aldehyde group (–CHO) and a tertiary dimethylamino group (–N(CH3)2) connected via a methylene linker, both positioned meta to each other on the benzene ring. The aldehyde enables electrophilic reactions such as condensation, reductive amination, and imine formation, while the tertiary amine provides a basic nitrogen for coordination, quaternization, or further functionalization. This bifunctionality is the primary reason the compound is valued as a versatile synthetic building block.

How should 3-[(Dimethylamino)methyl]benzaldehyde (B728005) be stored to maintain stability?

Aromatic aldehydes are susceptible to oxidation over time, so it is recommended to store B728005 in a tightly sealed container under inert atmosphere conditions where feasible, in a cool, dry, and well-ventilated location away from heat sources, light, and incompatible substances such as strong oxidizers and strong acids. Always refer to the specific storage conditions stated in the Aladdin Scientific SDS for this product, as lot-specific recommendations take precedence.

In what types of chemical reactions can 3-[(Dimethylamino)methyl]benzaldehyde be used?

This compound is useful in a broad range of reactions owing to its dual functionality. The aldehyde group can undergo Schiff base (imine) formation with primary amines, aldol-type condensations, Wittig reactions, and reductive amination. The dimethylaminomethyl group can participate in quaternization to give ammonium salts, or the nitrogen can serve as a coordinating atom in metal-complex formation. Collectively, these reactivities make it applicable in medicinal chemistry, ligand synthesis, fluorescent probe design, and materials science.

How do I confirm the purity of my lot of B728005 from Aladdin Scientific?

Each lot of B728005 is accompanied by a Certificate of Analysis (CoA) that reports lot-specific purity data, typically determined by gas chromatography (GC) or HPLC. The CoA can be accessed via the product page on the Aladdin Scientific website using the lot number printed on your product label, or by contacting Aladdin Scientific customer service. If additional structural confirmation such as NMR or mass spectrometry data is required, please request this from technical support.

Is 3-[(Dimethylamino)methyl]benzaldehyde the same as a Mannich base?

Yes, 3-[(Dimethylamino)methyl]benzaldehyde can be classified as a Mannich base, as it contains the characteristic aminomethyl (–CH2–NR2) motif that is the hallmark product of a Mannich reaction between an aldehyde, a secondary amine, and an active hydrogen compound. In this case, the compound can be viewed structurally as the product of a Mannich-type condensation introducing a dimethylaminomethyl group onto the benzaldehyde ring. This preformed Mannich base allows researchers to directly access the reactive aminomethyl functionality without conducting the Mannich reaction in situ.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for Mannich reaction and aldehyde chemistry.
2. Aladdin Scientific. Product page and Certificate of Analysis for 3-[(Dimethylamino)methyl]benzaldehyde, SKU B728005.

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