4-Hydroxy-3-methylbenzaldehyde is an aromatic compound that carries both an aldehyde group and a phenolic hydroxyl group on a single benzene ring, together with a methyl substituent positioned adjacent to the hydroxyl group. In the organic chemistry laboratory, this compound serves as a versatile building block because it presents two reactive centres of markedly different character within one small molecule. Its aldehyde group is ready to undergo condensation reactions and nucleophilic addition, while its phenolic group can be alkylated, acylated, or used as an attachment point in the assembly of larger and more complex molecules.
The property that makes this material a frequent choice is the balance it strikes between reactivity and ease of handling. As a hydroxy-substituted benzaldehyde, it reacts readily with primary amines to form Schiff bases, with active methylene compounds in Knoevenagel condensations, and can be reduced to the corresponding benzylic alcohol or oxidised to the carboxylic acid according to the requirements of the synthetic route. The presence of the methyl group ortho to the phenol contributes a degree of steric hindrance and a particular electronic influence that is often exploited to direct selectivity in substitution reactions.
In Indonesian laboratories, this building block is typically used in university and institutional organic synthesis work, where small-scale exploratory routes are developed before any scale-up is considered. It suits research groups preparing intermediates for further functionalisation, teaching laboratories demonstrating classical carbonyl and phenol chemistry, and analytical work requiring a well-defined aromatic reference material. Supplied by TCI, it is handled in the same way as other fine chemical reagents held in a controlled laboratory chemical store.
- Schiff base synthesis — the aldehyde group reacts directly with primary amines under mild conditions, making this a straightforward starting point for imine and ligand preparation work.
- Knoevenagel condensation — the aromatic aldehyde couples cleanly with active methylene compounds, allowing researchers to extend the carbon framework toward substituted alkene and coumarin-type targets.
- Selective reduction studies — the carbonyl can be reduced to the corresponding benzylic alcohol, giving a convenient substrate for comparing reducing agents and reaction conditions in method development.
- Controlled oxidation work — conversion of the aldehyde to the carboxylic acid provides a defined transformation for evaluating oxidant selectivity in the presence of a free phenolic hydroxyl group.
- Phenol functionalisation and linker chemistry — the hydroxyl group can be alkylated or acylated, or used as an attachment point when building larger and more structurally complex molecules.
| Brand | TCI |
|---|---|
| CAS number | 15174-69-3 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | available in standard TCI laboratory pack sizes; please confirm the required quantity when ordering |
| Physical form | — |
| Storage | keep in the original tightly closed container in a cool, dry, well-ventilated place away from light |
- Catalogue reference: H1419
Store the container tightly closed in a cool, dry and well-ventilated area, protected from direct sunlight and away from strong oxidising agents and sources of ignition. The original manufacturer packaging is the most suitable container; if transfer is necessary, use clean, dry, chemically compatible glass or approved plastic vessels and label them clearly with the substance name and CAS number. Handle in a fume hood, wearing safety glasses, chemical-resistant gloves and a laboratory coat, and avoid generating dust or breathing vapours. Keep the container closed when not in use to limit moisture uptake, return it promptly to the designated chemical store after weighing, and consult the manufacturer's safety data sheet before first use and for disposal guidance.
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