TCI D2042 3,4-Diacetoxybenzaldehyde is a non-heterocyclic building block: a benzaldehyde derivative in which both catechol hydroxyl groups have been protected as acetate esters. It is widely used in organic synthesis laboratories when researchers want to exploit the reactivity of the aldehyde group without interference from the easily oxidised free phenol groups. In other words, the compound serves as a protected form of 3,4-dihydroxybenzaldehyde, giving better control over reaction sequences and improving the likelihood of success in multi-step synthesis.
The property that makes this material a preferred choice is its combination of complementary functional groups. The aldehyde group is ready to take part in a range of classical reactions such as aldol condensation, the Wittig reaction, reductive amination, imine formation, and controlled oxidation or reduction. The two acetate groups, meanwhile, are relatively stable under neutral conditions yet are easily removed by mild base hydrolysis, so the catechol can be unmasked again at a later stage of the synthesis. As a solid, the material is straightforward to weigh, store, and measure accurately, which is practical for millimole-scale work.
Laboratories in Indonesia typically call on this building block in university and institutional research settings where multi-step organic synthesis is carried out. It fits the everyday routine of a synthesis laboratory: a solid intermediate that can be weighed out accurately for small-scale reactions, carried through a planned sequence, and deprotected when the free catechol is needed. Its predictable handling makes it well suited to teaching laboratories and research groups working at millimole scale.
- Protected catechol synthon — supplies the 3,4-dihydroxybenzaldehyde framework in masked form, so the free phenols cannot oxidise while the aldehyde group is being transformed in earlier steps.
- Aldol condensation work — the reactive aldehyde group readily forms carbon–carbon bonds, while the acetate protection prevents the phenolic positions from competing or interfering during the condensation.
- Wittig olefination — the aldehyde functionality couples cleanly with phosphonium ylides to extend the carbon skeleton, with both acetate groups remaining stable under the reaction conditions applied.
- Reductive amination and imine formation — the aldehyde reacts with amines to build nitrogen-containing targets, and the protected catechol can be unmasked afterwards by mild base hydrolysis.
- Multi-step synthesis planning — as a solid intermediate it is easy to weigh, store, and dose accurately, giving reliable control over reaction order in millimole-scale sequential synthesis.
| Brand | TCI |
|---|---|
| CAS number | 67727-64-4 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | available in standard laboratory research pack sizes — please refer to the current catalogue listing |
| Physical form | solid, convenient to weigh and measure accurately |
| Storage | keep in the tightly closed original container, protected from moisture |
- Catalogue number: D2042
Store the material in its tightly closed original container in a cool, dry place, away from moisture and direct sunlight, and keep it separated from strong bases and strong oxidising agents, since the acetate protecting groups are cleaved by base hydrolysis. Glass or the supplier's original bottle is the most suitable container; transfer only the amount required for the reaction at hand and reseal promptly. Handle the solid in a fume hood or a well-ventilated area, wearing safety glasses, gloves, and a laboratory coat, and avoid generating or inhaling dust during weighing. Use a clean, dry spatula to prevent contamination and moisture uptake, label all secondary containers clearly, and consult the manufacturer's safety data sheet before use and for waste disposal guidance.
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