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Description
TCI D2683 4',6'-Dimethoxy-2'-hydroxyacetophenone is an aromatic building block that carries an acetyl group, a single phenolic hydroxyl group in the ortho position, and two methoxy groups on the benzene ring. This particular arrangement of substituents makes it a classic starting material for constructing chromones, flavones, and other phenolic derivatives. In the laboratory, natural product researchers and medicinal chemists use the compound as an opening scaffold that is ready to be condensed, acylated, or cyclized into the oxygen-containing heterocyclic cores frequently encountered in plant secondary metabolites.
The property that most often drives its selection is the presence of a hydroxyl group ortho to the acetyl group, which allows internal hydrogen bonding while simultaneously setting up a cyclization pathway toward the pyranone ring through reactions such as the Baker-Venkataraman rearrangement. The two methoxy groups are electron-donating and therefore increase the reactivity of the ring toward electrophilic substitution, a characteristic that is useful when new groups need to be introduced at specific positions. Its form as a solid that remains stable under ordinary storage makes weighing straightforward, while its solubility in organic solvents such as acetone supports routine reaction setup.
In Indonesian laboratories, this building block fits naturally into natural product and medicinal chemistry programmes at universities and research institutes, where chromone and flavone frameworks are frequently targeted for synthesis and comparison against isolated plant metabolites. It is typically weighed out in small quantities for multi-step syntheses, used in method development work, and kept as a reference scaffold by groups that repeatedly build oxygen heterocycles as part of their ongoing research.
Laboratory Applications
- Chromone and flavone synthesis: the ortho-hydroxy acetophenone motif provides a direct entry to the pyranone ring, making it a standard precursor for these frameworks.
- Baker-Venkataraman rearrangement studies: the ortho hydroxyl adjacent to the acetyl group offers the exact arrangement required for the acyl migration step to proceed.
- Natural product scaffold construction: the dimethoxy substitution pattern mirrors oxygenation patterns commonly found in plant secondary metabolites targeted for total synthesis.
- Medicinal chemistry intermediate preparation: the reactive acetyl and phenolic positions allow chemists to elaborate the ring into diverse analogues for structure-activity studies.
- Electrophilic aromatic substitution work: the electron-donating methoxy groups activate the ring, letting researchers introduce new substituents at predictable positions under controlled conditions.
Specifications
- Brand: TCI
- CAS number: 90-24-4
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI catalogue pack sizes; please confirm the size required when ordering.
- Physical form: solid
- Storage: stable under ordinary laboratory storage conditions; keep the container tightly closed.
Handling and Storage
Store the container tightly closed in a cool, dry place away from direct sunlight, moisture, and sources of ignition, following the storage guidance supplied by the manufacturer on the label and safety data sheet. Keep the material in its original supplier container or in a clean, well-sealed amber glass bottle to limit exposure to air and light. Handle the solid in a fume hood or a well-ventilated area, wearing a laboratory coat, safety glasses, and chemical-resistant gloves. Avoid generating dust during weighing, use a clean spatula for each transfer, and close the container immediately afterwards. Segregate the material from strong oxidizing agents and strong bases, and dispose of residues and contaminated materials in accordance with your institution's chemical waste procedures.
