Azetidine

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Cat Number

INT503297

CAS Number

503-29-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

503-29-7

EINECS

207-963-8

Synonyms

1,3-Propylenimine

Molecular Formula

C3H7N

Molecular Weight

57.09

Smiles

C1CNC1

Appearance

Clear colorless liquid

Boiling Point

61-62℃

Relative Density

0.84

pKa

11.29

General Description

Azetidine (also known as cyclobutane with one carbon replaced by nitrogen, or trimethyleneimine) is a four-membered saturated nitrogen-containing heterocycle. As a small, strained, and basic nitrogen heterocycle, it serves as both a pharmacophore and a building block in pharmaceutical synthesis. The ring strain (~26 kcal/mol) makes the ring susceptible to nucleophilic ring-opening reactions, while the nitrogen is readily alkylated and acylated.

Mechanism of Action

Azetidine functions as a pharmacophore and building block. The four-membered ring constrains the nitrogen's geometry, reducing the N pyramidalization angle compared to piperidine, which can enhance selectivity for certain receptor subtypes. The ring is subject to nucleophilic ring-opening under acidic or activated conditions, which can be exploited in prodrug design. The nitrogen undergoes typical secondary amine reactions (alkylation, acylation, reductive amination) while the ring carbons undergo oxidation and substitution reactions.

Application

Azetidine is used as an intermediate in the synthesis of pharmaceuticals including the anti-Parkinson agent budipine and other CNS-active agents. It serves as a building block for the synthesis of azetidine-containing peptidomimetics, beta-amino acid derivatives, and constrained drug scaffolds. It is also used as a precursor for chiral auxiliaries, protecting groups, and in the synthesis of functional polymers.

Azetidine is a four-membered saturated nitrogen heterocycle found in FDA-approved drugs including azelnidipine, cobimetinib, and baricitinib. Green synthesis methods now enable high-yield, stereoselective production of azetidine heterocycles under mild reaction conditions. Azetidine-based ligands are applied in coupling reactions, asymmetric catalysis, and explosive materials. Synthetic routes to FDA-approved azetidine-containing drugs provide a foundation for developing novel azetidine heterocycles with broader pharmaceutical and industrial applications.

Fig. 1 Synthesis and applications of Azetidine. (Jaiswal S.; et al. 2025)

References

Jaiswal S, et al. Exploring azetidine containing heterocycles: From green synthesis to applications. Tetrahedron, 2025, 174: 134491.

What is the recommended storage condition for Azetidine?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

What documentation is provided with each batch of Azetidine?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

Is Azetidine available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

Can Azetidine be provided with custom specifications for synthetic applications?

Custom specifications including adjusted particle size, solvent residue limits, or additional purity testing can be arranged for qualified customers with defined requirements.

What quality standards govern the production of Azetidine?

Production is carried out under GMP-aligned quality systems with full traceability and documented quality controls for each manufacturing run.