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Description
TCI D2646 3,5-Di-tert-butylsalicylaldehyde, CAS number 37942-07-7, is a salicylaldehyde whose aromatic ring carries two bulky tert-butyl groups at the 3 and 5 positions. It belongs to the class of non-heterocyclic building blocks and is widely recognised as a starting material for the preparation of salen and salan ligands as well as a broad range of other Schiff base ligands. Because the aldehyde group and the neighbouring phenolic hydroxyl group sit adjacent to one another, the compound naturally forms a bidentate chelating framework once it has been condensed with an amine, which makes it one of the most frequently used materials in coordination chemistry and catalysis laboratories.
The property that makes this reagent so highly valued is the influence of its two bulky tert-butyl groups. The group at the 3 position shields the environment immediately around the metal centre, so that a substrate can only approach from certain directions, and this is precisely what governs selectivity in many salen-based catalysts. The group at the 5 position contributes electronically by pushing electron density into the ring while simultaneously protecting the para position against oxidative side reactions. Both groups also improve the solubility of the resulting metal complexes in non-polar organic solvents and suppress the formation of bridging species that would otherwise deactivate the catalyst.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on coordination chemistry, homogeneous catalysis, and ligand design, as well as in industrial R&D units that prepare metal complexes for evaluation. It is normally handled at the bench scale, weighed out for condensation reactions with primary amines or diamines, and stocked as a standard shelf item by groups that synthesise Schiff base ligands on a routine basis for further characterisation and catalytic testing.
Laboratory Applications
Salen ligand synthesis — condensation with chiral or achiral diamines gives the classic salen framework, with the 3-position tert-butyl group supplying the steric shielding that controls selectivity at the metal centre.
Salan ligand preparation — the same condensation followed by reduction of the imine bonds yields salan ligands, where the bulky substituents continue to define the coordination pocket around the metal.
General Schiff base ligand chemistry — reaction of the aldehyde group with primary amines produces bidentate chelating ligands, making this a routine entry point for ligand libraries in coordination chemistry.
Homogeneous catalyst development — metal complexes derived from this aldehyde benefit from improved solubility in non-polar organic solvents and reduced formation of bridging species that deactivate catalysts.
Coordination chemistry research and teaching — the adjacent aldehyde and phenolic hydroxyl groups make this an ideal substrate for demonstrating chelate formation and metal complex synthesis in research laboratories.
Specifications
Brand: TCI
CAS number: 37942-07-7
Chemical name: 3,5-Di-tert-butylsalicylaldehyde
Catalogue number: D2646
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes: available in the standard TCI catalogue pack sizes; please confirm the required quantity when ordering
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated place, away from direct sunlight, heat sources, and incompatible materials, and keep it in the original supplier packaging wherever possible. Amber glass or other opaque containers are appropriate for protecting the material from light. Handle the compound in a fume hood or in a well-ventilated working area, and wear standard laboratory personal protective equipment including safety goggles, chemically resistant gloves, and a laboratory coat. Avoid generating dust during weighing, close the container immediately after use, and always consult the manufacturer's safety data sheet before handling or disposal.
