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Description
TCI D2203, 3,4-Dibutoxy-3-cyclobutene-1,2-dione (CAS 2892-62-8), is better known as dibutyl squarate, an ester of squaric acid built on a four-membered cyclobutenedione framework. The compound holds an important position as a synthetic intermediate because the squarate core is able to bind two nucleophiles in sequence to give squaramides, a molecular motif now widely studied in organocatalysis, anion recognition, and medicinal chemistry. For synthesis laboratories, this material provides a short and reliable route toward structures that are electronically distinctive and otherwise difficult to construct.
The defining characteristic of this building block is the ability of its butoxy groups to act as leaving groups that can be displaced by amines in a stepwise fashion. Because the two substitutions occur one after the other, researchers can obtain either symmetrical or unsymmetrical squaramides simply by controlling the order and stoichiometry of reagent addition. The rigid, planar cyclobutenedione ring confers characteristic electronic properties: once both nitrogen atoms are attached, the system becomes a strong, fixed-distance double hydrogen-bond donor, a feature highly valued in catalyst and molecular receptor design. Its good solubility in common organic solvents further simplifies handling.
In Indonesian laboratories, this reagent is typically used in university and institutional research groups working on organic synthesis, catalyst development, and supramolecular or medicinal chemistry projects. It suits scale-flexible bench work where a small quantity of a specialised intermediate opens access to a family of target compounds. Groups preparing squaramide-based organocatalysts, anion receptors, or candidate bioactive scaffolds generally keep it as a stock intermediate rather than attempting to prepare the squarate diester in-house.
Laboratory Applications
- Squaramide synthesis — the stepwise displacement of both butoxy groups by amines allows direct preparation of symmetrical or unsymmetrical squaramides in a controlled two-stage sequence.
- Organocatalyst preparation — squaramides derived from this reagent serve as bifunctional hydrogen-bond donor catalysts, and the rigid ring geometry gives the fixed donor spacing such catalysts require.
- Anion recognition and receptor design — the resulting double hydrogen-bond donor motif binds anionic guests strongly, making this diester a practical starting point for supramolecular receptor construction.
- Medicinal chemistry scaffold work — the squaramide motif is widely studied in medicinal chemistry, and this intermediate provides a short route into that chemical space for analogue programmes.
- General non-heterocyclic building block use — as a reactive four-membered dione ester, it introduces an electronically unusual core that is difficult to construct by alternative synthetic routes.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 2892-62-8
- Chemical name: 3,4-Dibutoxy-3-cyclobutene-1,2-dione (dibutyl squarate)
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: supplied in standard TCI research-scale packaging; available pack sizes on request
- Storage: keep tightly closed in a cool, dry place away from moisture and direct light
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from direct sunlight, heat sources, and sources of moisture, since the reactive diester functionality can be degraded by water. Keep the material in its original tightly sealed supplier container, or transfer it to a clean, dry amber glass bottle with a chemically compatible closure. Handle in a fume hood using nitrile gloves, safety goggles, and a laboratory coat, and avoid contact with skin, eyes, and clothing. Store separately from amines and other strong nucleophiles, and from strong bases and oxidising agents. Allow cold containers to warm to room temperature before opening to prevent condensation. Consult the manufacturer's safety data sheet before use and dispose of residues as chemical waste.
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