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Description
TCI D3645 3,4-Dihydroxy-5-nitrobenzaldehyde is a non-heterocyclic building block that carries three distinct functional groups on a single aromatic ring: two adjacent hydroxyl groups forming a catechol motif, one nitro group, and one aldehyde group. This density of functionality makes it a highly productive starting material in the organic synthesis laboratory. The aldehyde group can be elaborated through condensation, reduction, oxidation, or reductive amination; the catechol motif participates in metal binding and antioxidant chemistry; and the nitro group contributes electron withdrawal that meaningfully alters the acidity and reactivity of the ring.
The property that makes this material a preferred choice is its distinctive nitrocatechol framework. The nitrocatechol motif is widely recognised in medicinal chemistry research as a scaffold examined in the development of catechol O-methyltransferase enzyme inhibitors, which makes this reagent a valuable precursor for the synthesis of model compounds and research derivatives. In addition, the active aldehyde group enables Knoevenagel reactions and condensations with active methylene compounds to obtain conjugated structures, while the pair of adjacent hydroxyl groups provides chelating capability toward metal centres.
In Indonesian laboratories, this reagent is typically used in university and institutional organic synthesis groups, medicinal chemistry research programmes, and materials chemistry work where a multifunctional aromatic starting material is required. It is generally handled at bench scale for method development, derivative preparation, and the construction of reference compounds, where a single well-defined building block allows several synthetic routes to be explored from one stock item rather than requiring separate specialised reagents.
Laboratory Applications
- Medicinal chemistry precursor work: the nitrocatechol framework is a scaffold studied in catechol O-methyltransferase inhibitor research, making this reagent a direct entry point for model compounds.
- Knoevenagel condensation chemistry: the active aldehyde group readily condenses with active methylene compounds, giving conjugated structures useful in both synthetic and materials-oriented research programmes.
- Aldehyde derivatisation studies: the formyl group supports reduction, oxidation, and reductive amination, allowing one starting material to generate several distinct derivative families.
- Metal coordination and chelation studies: the two adjacent hydroxyl groups forming the catechol motif provide binding capability toward metal centres in coordination chemistry investigations.
- Structure–reactivity investigations: the electron-withdrawing nitro group meaningfully alters ring acidity and reactivity, making this compound useful for studying substituent effects on aromatic systems.
Specifications
- Brand: TCI
- Product code: D3645
- CAS number: 116313-85-0
- Chemical name: 3,4-Dihydroxy-5-nitrobenzaldehyde
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale packaging; please confirm the required pack size when ordering
- Storage: store according to the manufacturer's label and the accompanying safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and incompatible materials, following the storage conditions stated on the manufacturer's label and safety data sheet. Keep the material in its original supplier container, or in a clean, chemically compatible and clearly labelled amber glass container if transfer is necessary, since catechol-containing compounds are generally sensitive to air and light. Handle the compound in a fume hood using appropriate personal protective equipment, including safety glasses, chemical-resistant gloves, and a laboratory coat. Avoid generating dust, avoid contact with skin and eyes, and close the container promptly after weighing. Dispose of residues and contaminated materials in accordance with applicable institutional and local chemical waste regulations.
