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Description
TCI C2119 1-(5-Chloro-2-hydroxyphenyl)ethan-1-one, also known as 5′-chloro-2′-hydroxyacetophenone, is an aromatic ketone carrying a hydroxyl group in the ortho position relative to the carbonyl. This ortho-hydroxyacetophenone arrangement is one of the most productive scaffolds in synthetic organic chemistry, because it serves as the starting point for building chromone, flavone, and benzofuran frameworks. In the laboratory, the material functions both as a versatile building block and as a ligand precursor, which is why it appears so frequently in research on natural product mimetics, medicinal chemistry, and coordination chemistry.
The characteristic property that makes this compound a preferred choice is the intramolecular hydrogen bond formed between the hydroxyl group and the adjacent carbonyl. This bond stabilises the molecule, influences its solubility behaviour, and — most importantly — directs subsequent reactions selectively, as seen in the Baker–Venkataraman rearrangement that produces 1,3-diketones as a route toward the chromone ring. The methyl ketone group remains reactive toward aldol and Claisen–Schmidt condensations for chalcone formation, while the chlorine atom contributes electron-withdrawing character and acts as a useful structural marker when assembling series of analogues.
In Indonesian laboratories, this building block is typically used in university research groups, postgraduate synthesis projects, and institutional chemistry facilities working on heterocyclic and natural-product-inspired targets. It suits benchtop-scale synthesis where a well-defined, reproducible starting material matters more than bulk quantity, and it is commonly drawn on for exploratory route development, method optimisation, and the preparation of reference compounds that later feed into biological screening or coordination chemistry studies.
Laboratory Applications
- Chromone and flavone synthesis — the ortho-hydroxy ketone arrangement provides exactly the arrangement required for ring closure, making this compound a direct entry point into these frameworks.
- Baker–Venkataraman rearrangement studies — the intramolecular hydrogen bond directs the rearrangement selectively toward 1,3-diketone intermediates that subsequently cyclise into the chromone ring system.
- Chalcone preparation via Claisen–Schmidt condensation — the methyl ketone group stays reactive toward aldol-type condensation with aromatic aldehydes under standard laboratory conditions.
- Benzofuran scaffold construction — the phenol and adjacent ketone functionality together support cyclisation routes leading to benzofuran-based structures for heterocyclic chemistry research.
- Ligand precursor work in coordination chemistry — the neighbouring hydroxyl and carbonyl groups form a natural chelating motif suitable for preparing metal complexes.
Specifications
- Brand: TCI
- CAS number: 1450-74-4
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Chemical name: 1-(5-Chloro-2-hydroxyphenyl)ethan-1-one (5′-chloro-2′-hydroxyacetophenone)
- Pack sizes: available in standard laboratory research pack sizes as supplied by the manufacturer
- Storage: keep in the original tightly closed container, protected from light and moisture
Handling and Storage
Store the material in a cool, dry, well-ventilated area, keeping the container tightly closed and protected from direct sunlight and moisture. The original manufacturer container is the most suitable primary packaging; if transfer is necessary, use clean, dry, chemically compatible glassware with a secure closure and clear labelling. Handle in a fume hood, and wear safety goggles, gloves, and a laboratory coat. Avoid contact with skin and eyes and avoid inhaling any dust. Keep away from strong oxidising agents and ignition sources, and always consult the manufacturer's safety data sheet before use.
