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Description
TCI D3498 is 3,5-dimethylbenzaldehyde, an aromatic aldehyde bearing two methyl groups positioned meta to the formyl group. It belongs to the non-heterocyclic building blocks family and serves as a highly versatile starting material, because the aldehyde function is among the most reactive functional groups in organic chemistry. From this single handle, researchers can perform condensation with amines to form imines and Schiff bases, Wittig and aldol reactions for chain extension, reduction to the corresponding benzylic alcohol, and oxidation to the matching aromatic carboxylic acid.
The property that makes this compound a preferred choice is its 3,5-dimethyl substitution pattern, which is symmetrical with respect to the formyl group. This symmetry simplifies the interpretation of nuclear magnetic resonance spectra, so characterization of downstream derivatives becomes considerably easier. Both methyl groups act as weak electron donors and impose steric hindrance on the flanks of the ring, which is useful when a researcher wants to control the dihedral angle between rings in biaryl compounds or tune the electron density of a ligand. In addition, the methyl groups can be further functionalized through radical halogenation or oxidation, opening additional synthetic routes.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, ligand design, and materials chemistry, where a well-defined aromatic aldehyde is needed as a reliable entry point. It suits methodology development work, the preparation of Schiff base ligands, and the synthesis of derivative libraries in which straightforward spectroscopic confirmation of each intermediate keeps a multi-step project moving efficiently.
Laboratory Applications
- Schiff base and imine synthesis: the reactive formyl group condenses cleanly with primary amines, giving well-defined ligands whose symmetric aromatic ring simplifies structural confirmation by NMR.
- Wittig and aldol chain extension: the aldehyde serves as the electrophilic partner for carbon–carbon bond formation, allowing researchers to build longer or branched frameworks from a single aromatic core.
- Reduction to benzylic alcohol: the formyl group is readily reduced to the corresponding alcohol, providing a hydroxymethyl handle for etherification, esterification, or further substitution chemistry.
- Oxidation to aromatic carboxylic acid: converting the aldehyde gives the matching 3,5-dimethyl-substituted acid, a useful precursor for amides, esters, and coordination chemistry applications.
- Biaryl and ligand design studies: the flanking methyl groups provide steric hindrance and weak electron donation, letting researchers control inter-ring dihedral angles and modulate electron density on the ligand.
Specifications
- Brand: TCI
- CAS number: 5779-95-3
- Chemical name: 3,5-Dimethylbenzaldehyde
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale packaging; please confirm the pack size options when ordering
- Storage: keep in the tightly closed original container as indicated on the manufacturer's label
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and incompatible materials such as strong oxidizing agents. Aromatic aldehydes are generally sensitive to air oxidation, so minimize headspace exposure and reseal the container promptly after each use; keeping the material under an inert atmosphere is advisable for long-term storage. Handle inside a fume hood using appropriate personal protective equipment, including safety goggles, chemical-resistant gloves, and a laboratory coat. Use clean, dry glassware or the original manufacturer's container for storage and transfer, avoid contact with skin and eyes, and always consult the manufacturer's safety data sheet before use.
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