TCI B6012 is tert-Butyl 3-(2-Ethoxy-2-oxoethylidene)azetidine-1-carboxylate, an azetidine building block that carries a conjugated α,β-unsaturated ester at the 3-position together with a Boc protecting group on the ring nitrogen. The structure combines two useful elements in a single molecule: a compact four-membered heterocyclic framework and a Michael acceptor group that is ready to react. In organic synthesis laboratories, a material of this kind serves as an efficient bridge for building side-chain substituted azetidine derivatives without having to go through ring-forming steps that normally demand special conditions and give low yields.
The characteristic that makes this compound a preferred choice is the directed reactivity of the conjugated double bond attached to the ethyl ester. The carbonyl group withdraws electron density, so the β-carbon becomes strongly electrophilic and is ready to accept nucleophiles in conjugate addition reactions, whether from amines, thiols, malonates, or suitable organometallic reagents. The ethyl ester itself can be hydrolysed to a carboxylic acid, reduced to an alcohol, or converted into an amide, so the range of accessible derivatives is very wide. The Boc group keeps the azetidine nitrogen protected throughout these transformations and can be removed under acidic conditions when the free amine is needed.
In Indonesian laboratories, building blocks of this type are used in university research groups, pharmaceutical development units, and contract synthesis facilities that prepare small-molecule libraries. The azetidine motif is valued in medicinal chemistry programmes for the rigidity and reduced conformational freedom it introduces into a candidate structure. Because the material is supplied ready to use, research teams can move directly to the derivatisation step, which shortens experimental timelines and reduces dependence on multi-step in-house ring construction.
- Conjugate addition chemistry: the electron-poor β-carbon of the unsaturated ester accepts amine, thiol, malonate, and organometallic nucleophiles cleanly, giving 3-substituted azetidine products in a single controlled step.
- Medicinal chemistry library synthesis: the rigid four-membered azetidine core introduces conformational restriction into candidate molecules, a design element frequently sought when optimising small-molecule leads in drug discovery programmes.
- Ester functional group interconversion: the ethyl ester can be hydrolysed to the carboxylic acid, reduced to the alcohol, or converted to amides, letting one starting material serve many downstream derivative targets.
- Protecting group strategy development: the Boc group on the ring nitrogen survives a wide range of transformations and is cleanly removed under acidic conditions to liberate the free azetidine amine when required.
- Heterocyclic scaffold assembly: the compound avoids the demanding ring-closure steps normally needed to build azetidines, letting synthetic chemists access substituted derivatives without low-yielding cyclisation sequences.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 1002355-96-5 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in standard TCI research-scale catalogue pack sizes; please confirm the currently listed options when ordering |
| Physical form | — |
| Storage | keep under the storage conditions stated on the manufacturer's label and safety data sheet |
- Chemical name: tert-Butyl 3-(2-Ethoxy-2-oxoethylidene)azetidine-1-carboxylate
Store the container tightly closed in a cool, dry, well-ventilated area away from heat sources, direct sunlight, and incompatible materials, following the storage conditions printed on the manufacturer's label and safety data sheet. Keep the material in its original supplier container or in a clean, chemically compatible amber glass vessel with a secure closure, and label all secondary containers clearly. Handle the compound in a fume hood using safety goggles, nitrile gloves, and a laboratory coat. As an α,β-unsaturated ester, the material is an electrophilic Michael acceptor, so avoid skin and eye contact and avoid inhaling any vapour or dust. Review the manufacturer's safety data sheet before first use, minimise exposure to moisture when transferring, and dispose of residues and contaminated consumables through the laboratory's chemical waste stream.
—