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Description
TCI D4332, 4,4'-Dibromo-1,1'-spirobiindane-7,7'-diol, is a non-heterocyclic building block based on a spirobiindane framework, in which two indane units are joined through a single shared spiro carbon atom. This spiro connection produces a rigid, non-planar molecule whose two aromatic planes are held perpendicular to one another. In the laboratory, the compound serves as a parent scaffold for constructing ligands and catalysts, most notably the SPINOL family of derivatives that is widely discussed in the modern literature of asymmetric catalysis and coordination chemistry.
The main advantage of this building block lies in the combination of conformational rigidity and the presence of three distinct types of functionalisation points. The two phenolic hydroxyl groups can be converted into cyclic phosphates, phosphites, ethers, or esters, while the two bromine atoms provide handles for metal-catalysed cross-coupling reactions such as Suzuki and Buchwald–Hartwig couplings, or for halogen–metal exchange. Researchers can therefore tune the electronic properties and steric bulk around the active centre of a catalyst in a systematic manner. The spiro framework also confers axial chirality that is stable towards racemisation, a property highly valued in catalyst design.
In Indonesian laboratories, this material is typically used by university research groups, graduate students, and institutional research centres working on synthetic organic chemistry, catalyst development, and coordination chemistry. It is generally handled at the small research scale, where a compact quantity of a well-defined scaffold supports method development, ligand synthesis studies, and exploratory route-finding work. The TCI catalogue code D4332 makes it straightforward to reference the same material consistently across procurement records, laboratory notebooks, and published experimental sections.
Laboratory Applications
- Ligand synthesis: the rigid spirobiindane diol serves as the parent scaffold from which SPINOL-type ligands are constructed for use in coordination chemistry studies.
- Asymmetric catalysis research: the axial chirality of the spiro framework is stable towards racemisation, making it a valued starting point for chiral catalyst design.
- Cross-coupling chemistry: the two bromine atoms act as reliable handles for metal-catalysed Suzuki and Buchwald–Hartwig couplings that introduce new aryl or amino substituents.
- Phosphorus-based derivative preparation: the two phenolic hydroxyl groups can be converted into cyclic phosphates or phosphites for catalyst and organocatalyst development work.
- Structure–activity tuning studies: the three distinct functionalisation points allow researchers to adjust electronic properties and steric bulk around an active centre systematically.
Specifications
- Brand: TCI (catalogue code D4332)
- CAS number: 681481-91-4
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Chemical name: 4,4'-Dibromo-1,1'-spirobiindane-7,7'-diol
- Pack sizes: research-scale packaging as offered in the TCI catalogue for this catalogue code
- Storage note: keep in the original closed container under the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, and incompatible chemicals, and follow the storage conditions printed on the manufacturer's label and safety data sheet. Keep the material in its original supplier container, or in a clean, chemically compatible and clearly labelled vessel if transfer is required. Handle the compound in a fume hood using standard laboratory personal protective equipment, including a laboratory coat, safety goggles, and suitable chemical-resistant gloves. Minimise the generation of dust during weighing and transfer, close the container promptly after use, and consult the safety data sheet before first use and before any disposal of residues.
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