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Description
TCI C2183 3-Chloro-4-hydroxybenzaldehyde is a substituted benzaldehyde carrying a phenolic hydroxyl group and a chlorine atom on the same aromatic ring. The compound belongs to the non-heterocyclic building block family and occupies an important position in organic synthesis laboratories because it presents three distinct functional groups within one compact aromatic framework. The aldehyde group is ready for condensation and carbon-carbon bond forming reactions, the phenol can be etherified or esterified to tune molecular properties, while the chlorine atom acts as an electronic director and simultaneously serves as an entry point for cross-coupling reactions.
The property that makes this material a frequent choice is the high yet controllable reactivity of its aromatic aldehyde. This aldehyde reacts smoothly in aldol condensations, Knoevenagel reactions, imine and hydrazone formation, and reductive amination. The phenolic hydroxyl group improves solubility in polar solvents and can be activated as a nucleophile under basic conditions to form aryl ethers. The presence of the chlorine atom ortho to the phenol influences the acidity of the hydroxyl group as well as the electron density distribution around the ring, giving researchers a predictable handle on selectivity when planning multi-step sequences on a single scaffold.
In Indonesian laboratories, this building block is typically used in university and institutional organic synthesis groups, in medicinal chemistry and materials research programs, and in analytical work that requires a well-defined aromatic reference substrate. It is commonly ordered in small research quantities for method development, thesis and dissertation projects, and exploratory route-scouting, where a single reagent offering three orthogonal reactive sites reduces the number of separate chemicals a laboratory must stock and handle.
Laboratory Applications
Knoevenagel and aldol condensation work — the aromatic aldehyde reacts smoothly with active methylene compounds, making it a dependable partner for building extended conjugated frameworks in synthesis studies.
Imine, Schiff base, and hydrazone preparation — the readily accessible aldehyde group condenses with primary amines and hydrazines, supporting ligand synthesis and derivative characterization projects.
Reductive amination routes — chemists convert the aldehyde into secondary and tertiary amines in a controlled manner, a common step in medicinal chemistry scaffold construction and analogue preparation.
Aryl ether and ester synthesis — the phenolic hydroxyl can be alkylated or acylated under basic conditions, allowing systematic modification of polarity and molecular properties.
Cross-coupling and electronic tuning studies — the ring chlorine serves as an entry point for coupling chemistry while directing electron density, giving predictable control over regioselectivity in multi-step sequences.
Specifications
Brand: TCI
CAS Number: 2420-16-8
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Product Code: C2183
Pack sizes: available in standard research-scale catalogue pack sizes; please confirm the currently listed options when ordering.
Storage: keep in a tightly closed original container, in a cool, dry, well-ventilated place away from light and incompatible materials.
Handling and Storage
Store this building block in its original tightly closed container in a cool, dry, and well-ventilated area, protected from direct sunlight, moisture, and heat sources. Amber glass or the supplier's original packaging is suitable, since phenolic aldehydes are generally sensitive to light and prolonged air exposure. Handle the material inside a fume hood using nitrile gloves, safety goggles, and a laboratory coat, and avoid inhaling dust or generating aerosols. Keep the compound away from strong oxidizing agents and strong bases. Always consult the manufacturer's Safety Data Sheet before use, and dispose of residues and contaminated consumables through the laboratory's designated chemical waste stream in accordance with applicable local regulations.
