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Description
TCI D4742, CAS 3321-92-4, is 3',5'-Dichloro-2'-hydroxyacetophenone, an aromatic building block that carries an acetyl group, a hydroxyl group in the ortho position, and two chlorine atoms on the benzene ring. The ortho-hydroxyacetophenone motif is one of the most classical and productive starting materials in organic chemistry because it serves as a gateway to a wide range of oxygen heterocyclic frameworks. In the laboratory, this compound is widely used to construct chromones, flavones, coumarins, and chelating ligands capable of binding metal ions strongly.
The strength of this compound lies in the ortho relationship between the hydroxyl group and the carbonyl group, which produces an intramolecular hydrogen bond. This interaction stabilises the molecule while also making the framework an effective chelating partner for metal ions. The methyl ketone group is readily transformed through aldol condensation, the Claisen reaction, the Baker–Venkataraman rearrangement, and the formation of chalcones and Schiff bases. The two chlorine atoms on the ring provide electron withdrawal that increases the acidity of the phenolic hydroxyl group and can at the same time serve as points for further functionalisation under suitable coupling conditions.
In Indonesian laboratories, this building block belongs in organic chemistry and inorganic chemistry work, where the same reagent supports both heterocycle synthesis and coordination chemistry. It is handled as a standard research-scale synthetic intermediate on the bench and in fume-hood operations, drawn on for method development, structure–activity exploration, and the preparation of ligands and heterocyclic scaffolds for further study. Its classical reactivity makes it equally suitable for teaching-level synthesis exercises and for exploratory research programmes.
Laboratory Applications
- Chromone and flavone synthesis — the ortho-hydroxyacetophenone motif is the classical entry point to these oxygen heterocycles, cyclising readily from the acetyl and phenolic groups.
- Coumarin preparation — the ortho-positioned hydroxyl and reactive methyl ketone together give the framework needed to close the benzopyranone ring under standard condensation conditions.
- Chelating ligand construction — the ortho hydroxyl–carbonyl arrangement forms an effective chelating pocket, allowing the preparation of ligands that bind metal ions strongly.
- Chalcone and Schiff base formation — the methyl ketone group is easily transformed by aldol condensation and Claisen-type reactions, giving direct access to both product classes.
- Baker–Venkataraman rearrangement studies — this compound is a standard substrate for the rearrangement, making it useful for method development and heterocyclic route planning.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 3321-92-4
- Chemical name: 3',5'-Dichloro-2'-hydroxyacetophenone
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Catalogue code: D4742
- Pack sizes: available in standard research-scale laboratory pack sizes as listed by the manufacturer
- Storage: store according to the manufacturer's label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from direct sunlight, heat sources, moisture, and incompatible chemicals such as strong oxidising agents and strong bases. Keep the material in its original manufacturer container, or transfer it to a clean, chemically compatible, clearly labelled glass container with a secure closure. Handle in a fume hood using safety glasses, chemical-resistant gloves, and a laboratory coat, and avoid inhalation of dust and contact with skin and eyes. Return the container promptly after weighing to limit exposure to atmospheric moisture, keep a copy of the safety data sheet accessible at the point of use, and dispose of residues and contaminated materials as chemical waste in line with institutional procedures.
