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Description
TCI C2249 5-Chloro-3-nitrosalicylaldehyde is a salicylaldehyde derivative carrying both a chloro group and a nitro group on its aromatic ring. The molecule offers three reactive handles at once: the aldehyde group, the phenolic hydroxyl group in the ortho position, and the nitro group, which can be reduced to an amine. In synthetic chemistry and coordination chemistry laboratories, this compound serves as a favoured starting material for building Schiff bases, salen ligands, and a range of oxygen heterocyclic frameworks such as coumarins and benzofurans through condensation reactions whose procedures are already well established.
The property that makes it attractive is the electronic influence that the nitro and chloro groups exert over the whole molecule. Both are electron-withdrawing, so they raise the acidity of the phenolic hydroxyl group while simultaneously increasing the electrophilicity of the carbonyl carbon, which makes condensation with primary amines proceed more rapidly and more completely. When the compound is converted into a Schiff base ligand, those electron-withdrawing groups modify the electronic character of the coordinated metal centre, so the catalytic activity and the magnetic behaviour of the resulting complex can be tuned deliberately. Intramolecular hydrogen bonding between the ortho hydroxyl and the imine nitrogen further stabilises the products that are formed.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on ligand design, coordination compounds, and organic synthesis, as well as in method development for heterocyclic chemistry. It is normally purchased in small research quantities rather than bulk, and is handled at the bench for multi-step syntheses in which a well-defined, reliably supplied intermediate matters more than volume. Its established reaction procedures make it suitable for graduate-level project work and for laboratories building reproducible synthetic routes.
Laboratory Applications
- Schiff base synthesis: the electron-poor carbonyl carbon reacts readily with primary amines, giving fast, complete condensation and cleanly isolable imine products for structural and spectroscopic study.
- Salen-type ligand preparation: the ortho hydroxyl and aldehyde pairing provides the classical binding pocket, while the chloro and nitro substituents tune the donor strength of the resulting ligand.
- Coordination complex and catalyst development: ligands derived from this aldehyde alter the electronic environment of the bound metal centre, allowing catalytic activity to be adjusted by deliberate substituent design.
- Oxygen heterocycle construction: established condensation procedures convert this material into coumarin and benzofuran frameworks, making it a practical entry point for heterocyclic route development.
- Nitro reduction chemistry: the nitro group can be reduced to an amine, opening a second functional handle for building multi-substituted aromatic intermediates in longer synthetic sequences.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS Number: 16634-90-5
- Product Code: C2249
- Chemical Name: 5-Chloro-3-nitrosalicylaldehyde
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes and storage conditions: refer to the manufacturer's current catalogue listing and product label
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated place, away from direct sunlight, heat sources, and incompatible materials, and follow the storage conditions stated on the manufacturer's label and Safety Data Sheet. Keep the material in its original supplier container, or in a chemically compatible, clearly labelled amber glass bottle if transferred. Handle in a fume hood using nitrile gloves, safety goggles, and a laboratory coat, and avoid inhalation of dust and contact with skin and eyes. Weigh out portions carefully to limit dust generation, close the container immediately after use, and dispose of residues and contaminated materials according to institutional chemical waste procedures.
