tert-Butyl 3-(Aminomethyl)-3-hydroxyazetidine-1-carboxylate TCI D6492

Chemical Identity

Other names: 1-Boc-3-hydroxy-3-(aminomethyl)azetidine · 1,1-Dimethylethyl 3-(Aminomethyl)-3-hydroxy-1-azetidinecarboxylate · tert-Butyl 3-(Aminomethyl)-3-hydroxy-1-azetidinecarboxylate
CAS No.: 1008526-71-3
PubChem: CID 57415900
Formula: C9H18N2O3
Molecular weight: 202.25 g/mol
Purity: >95.0%(GC)(T)
Storage: 0-10°C

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: tert-butyl 3-(aminomethyl)-3-hydroxyazetidine-1-carboxylate
SMILES: CC(C)(C)OC(=O)N1CC(C1)(CN)O
InChIKey: NVEHYSKQUSAZBP-UHFFFAOYSA-N
MDL: MDL17015986

Rp 1.856.400,00

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TCI D6492 tert-Butyl 3-(Aminomethyl)-3-hydroxyazetidine-1-carboxylate is a building block that presents three useful functional groups at once within a remarkably compact azetidine framework: a primary amine on the aminomethyl group, a tertiary hydroxyl on the third carbon of the ring, and a ring nitrogen protected as a Boc carbamate. In the synthesis laboratory, this compound serves as a source of a rigid amino alcohol motif that is ready to be installed onto a target molecule, giving researchers a polar attachment point together with an element of structural rigidity without having to work through a long, multi-step sequence prone to loss of yield.

The property that makes this material sought after is its balance between polarity and rigidity. The tertiary hydroxyl group adds hydrophilic character that helps improve aqueous solubility, while its position on a quaternary ring carbon leaves it relatively sterically hindered and therefore less likely to interfere with reactions at the primary amine. The primary amine itself is a highly reactive nucleophile, ready to form amides, sulfonamides, ureas, and thioureas, or to create new bonds through reductive amination. The Boc group on the ring nitrogen ensures that these reactions proceed at the intended position, and it can be removed later when the ring nitrogen is needed for further elaboration.

In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis and medicinal chemistry, as well as in industrial research units developing new molecules. It is usually ordered in small quantities for exploratory routes and analogue series, then handled on a milligram to gram scale in standard synthetic glassware. Because it arrives with the ring nitrogen already protected, teams can begin building their target structures immediately rather than preparing the protected intermediate in house.

Related TCI products

Medicinal chemistry analogue synthesis: the compact azetidine core introduces three-dimensional character and a polar hydroxyl group that can improve aqueous solubility in candidate molecules under investigation.
Amide and sulfonamide coupling: the reactive primary amine readily forms amide, sulfonamide, urea, and thiourea linkages, allowing rapid assembly of diverse compound sets from a single common intermediate.
Reductive amination routes: the primary amine couples cleanly with aldehydes and ketones to generate secondary amines, providing a straightforward way to extend molecular frameworks from this starting point.
Rigid amino alcohol scaffold installation: the fixed geometry of the four-membered ring constrains conformational freedom, which is valuable when a defined spatial arrangement of donor groups is required.
Orthogonal protection strategies: the Boc-protected ring nitrogen allows chemistry to be performed selectively at the primary amine first, with the ring nitrogen deprotected and functionalised in a later, separate step.

Brand	TCI (Tokyo Chemical Industry)
CAS number	1008526-71-3
Molecular formula	—
Purity	—
Category	Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes	supplied in standard research-scale packs; please confirm the available size when ordering
Physical form	—
Storage	keep in the tightly closed original container under the conditions stated on the manufacturer's label and safety data sheet

Product code: TCI D6492

Store the material in its tightly closed original container, kept in a cool, dry, and well-ventilated place away from direct sunlight, moisture, and ignition sources, and follow the specific storage conditions printed on the manufacturer's label and safety data sheet. Boc-protected amino compounds are best protected from humidity and acidic vapours, so reseal the container promptly after each use. Handle the material in a fume hood while wearing a laboratory coat, chemical-resistant gloves, and safety goggles. Weigh out quantities using clean, dry spatulas and glassware to avoid contaminating the bulk stock. Consult the safety data sheet before first use and dispose of residues and contaminated consumables through your institution's chemical waste procedures.

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