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Description
TCI D5793 2,5-Dibromoterephthalaldehyde is an aromatic benzene derivative carrying two aldehyde groups at the 1 and 4 positions (the terephthalaldehyde arrangement) together with two bromine atoms at the 2 and 5 positions. This symmetrical arrangement makes it a highly valuable non-heterocyclic building block in organic synthesis laboratories, because a single molecule supplies two distinct classes of reactive site at once. Its role in the laboratory is to serve as a core scaffold for constructing larger molecules, ranging from ligands and organic dyes through to porous materials and conjugated polymers that require linear symmetry.
The characteristic that leads chemists to select this material is the orthogonality of its reactivity. The aldehyde groups are readily directed into condensation chemistry such as Schiff base formation with amines, Wittig and Knoevenagel reactions, as well as controlled reduction and oxidation. The two C–Br bonds on the ring, meanwhile, are classic entry points for palladium-catalysed cross-coupling reactions such as Suzuki–Miyaura, Sonogashira, Stille and Heck. Chemists can choose the order of transformation so that one starting material can be developed into many different derivatives. The molecular symmetry also simplifies the design of extended structures.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, materials chemistry and polymer chemistry, where a symmetrical linear core is needed as the starting point of a multi-step route. It is generally purchased in small research quantities for method development, thesis and dissertation work, and exploratory syntheses, then stored alongside other fine chemicals in the group's dedicated organic reagent inventory.
Laboratory Applications
Schiff base and imine ligand synthesis: the two aldehyde groups condense with primary amines to give symmetrical bis-imine ligands useful in coordination chemistry studies.
Palladium-catalysed cross-coupling: both C–Br bonds act as reliable entry points for Suzuki–Miyaura, Sonogashira, Stille and Heck reactions to extend the aromatic framework.
Conjugated polymer preparation: the linear, symmetrical 1,4-substitution pattern allows controlled chain extension for materials work that depends on an extended conjugated backbone.
Porous and framework material research: the rigid symmetrical core with two condensable aldehyde sites supports the assembly of ordered network structures from a single monomer.
Organic dye and chromophore synthesis: Wittig and Knoevenagel condensations at the aldehyde positions build extended π-systems around a defined symmetrical central scaffold.
Specifications
Brand: TCI
CAS number: 63525-48-4
Chemical name: 2,5-Dibromoterephthalaldehyde
Catalogue reference: D5793
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes: available in the standard research pack sizes offered by the manufacturer for this catalogue item
Storage: keep in the tightly closed original container in a cool, dry, well-ventilated place away from light
Handling and Storage
Store the material in its original tightly closed container in a cool, dry and well-ventilated area, protected from direct sunlight and away from sources of heat or ignition. Amber glass or the manufacturer's supplied packaging is suitable, and containers should be resealed promptly after each use to limit exposure to moisture and air. Handle in a fume hood using a laboratory coat, chemical-resistant gloves and safety glasses, and avoid inhalation of dust and contact with skin and eyes. Keep the material separate from strong oxidising agents, strong bases and incompatible reagents. Weigh out only the quantity required, clean any spillage immediately, and dispose of residues and contaminated consumables through the laboratory's chemical waste stream. Always consult the manufacturer's Safety Data Sheet before use.
