TCI D4109 Di-tert-butyl Iminodiacetate, CAS number 85916-13-8, is an iminodiacetate derivative in which both carboxylate groups have been protected as tert-butyl esters, leaving a single secondary amine free to react. In the laboratory, this compound serves as a building block for assembling chelating ligands, molecular linkers, and peptidomimetic intermediates. Its secondary amine is ready to undergo alkylation, acylation, or reductive amination, while the two tert-butyl esters keep the acid functions masked until the final stage of a synthesis, at which point both can be removed simultaneously under acidic conditions.
The property that makes this material a widely preferred choice is its efficient dual protection strategy: a single reagent immediately supplies two protected acid groups at once, so the number of synthetic steps can be trimmed considerably. Tert-butyl esters are well known for their stability toward bases and nucleophiles, yet they are easily cleaved with an acid such as trifluoroacetic acid without requiring hydrogenation, which makes them suitable for use alongside functional groups that are sensitive to reduction. The iminodiacetate framework is also a classic chelating motif capable of binding metal ions strongly, so the compound frequently becomes a starting material where controlled metal coordination is the design objective.
In Indonesian laboratories, this building block is typically used in university research groups, synthetic and medicinal chemistry laboratories, and analytical or materials development units that prepare their own ligands and linkers rather than purchasing finished conjugates. It is normally ordered in the small research quantities appropriate to multi-step exploratory synthesis, handled inside a fume hood as part of routine organic workflows, and stored together with other moisture-sensitive protected intermediates in the laboratory chemical store.
- Chelating ligand synthesis: the iminodiacetate framework is a classic metal-binding motif, and the protected esters allow the ligand skeleton to be elaborated before the acid groups are finally revealed.
- Molecular linker construction: the free secondary amine provides a single reactive point for joining two molecular fragments, while both carboxyl functions stay masked throughout the coupling sequence.
- Peptidomimetic intermediate preparation: the compound introduces a branched diacid unit into peptide-like structures, with acid-labile protection that matches the deprotection chemistry commonly used in peptide work.
- Reductive amination and alkylation chemistry: the secondary amine reacts readily with alkylating agents, acyl donors, and carbonyl compounds, giving direct access to substituted iminodiacetate derivatives in one step.
- Multi-step synthesis requiring late-stage deprotection: both tert-butyl esters survive basic and nucleophilic conditions and are then cleaved together with acid, removing the need for a separate hydrogenation stage.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 85916-13-8 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | available in standard TCI research pack sizes; please confirm the currently listed packaging option when ordering |
| Physical form | — |
| Storage | keep in a cool, dry, well-ventilated place in a tightly closed original container, away from moisture and strong acids |
- Catalogue number: D4109
Store the container tightly closed in a cool, dry, well-ventilated area, protected from moisture, direct sunlight, and heat sources, and keep it segregated from strong acids and strong oxidising agents, since acidic conditions cleave the tert-butyl ester protection. Retain the material in its original supplier container or in an equivalent chemically compatible, tightly sealed vessel with a clearly legible label. Handle the compound inside a fume hood using safety glasses, gloves, and a laboratory coat, avoid contact with skin and eyes and the breathing of any dust or vapour, and close the container promptly after weighing to limit moisture uptake. Consult the manufacturer's safety data sheet before use and dispose of residues and contaminated materials as chemical waste according to institutional procedures.
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