Azetidine

Base Information

• Chemical Name: Azetidine
• CAS No.: 503-29-7
• Deprecated CAS: 156423-81-3
• Molecular Formula: C3H7N
• Molecular Weight: 57.0953
• Hs Code.: 29339990
• European Community (EC) Number: 207-963-8
• UNII: 37S883XDWR
• DSSTox Substance ID: DTXSID8060117
• Nikkaji Number: J79.636K
• Wikipedia: Azetidine
• Wikidata: Q425376
• Metabolomics Workbench ID: 54298
• ChEMBL ID: CHEMBL2171713
• Mol file: 503-29-7.mol

Synonyms:1,3-propylenimine;azacyclobutane;azetidine;trimethylenimine

Chemical Property of Azetidine

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Melting Point: -70°C
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 64.9 °C at 760 mmHg
• PKA: 11.29(at 25℃)
• Flash Point: ?5°F
• PSA: 12.03000
• Density: 0.851 g/cm³
• LogP: 0.30850
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive/Air Sensiti
• Water Solubility.: miscible
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 57.057849228
• Heavy Atom Count: 4
• Complexity: 17.2

Purity/Quality:

98% ^*data from raw suppliers

Azetidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CNC1
• General Description: Azetidine is a versatile scaffold identified as a promising core structure for developing selective and potent colony stimulating factor-1 receptor (CSF-1R) Type II inhibitors, demonstrating significant therapeutic potential for conditions like rheumatoid arthritis. Through structure-based drug design and docking models, optimized azetidine derivatives, such as compound **4a** (IC50 = 9.1 nM), were shown to effectively bind the DFG-out conformation of CSF-1R, validating their role as Type II kinase inhibitors. This highlights the scaffold's utility in designing targeted kinase inhibitors with high specificity.

Technology Process of Azetidine

There total 28 articles about Azetidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

azetidine hydrochloride (78797-58-7,78797-59-8,78797-62-3,36520-39-5,65546-09-0) → azetidine (503-29-7)

Guidance literature:

With potassium hydroxide; In water; at 20 - 95 ℃; for 3h; Inert atmosphere;

DOI:10.1021/op700052u

Reference yield: 85.0%

azetidine hydrochloride (78797-58-7,78797-59-8,78797-62-3,36520-39-5,65546-09-0) + potassium hydroxide → azetidine (503-29-7)

Guidance literature:

In water; at 90 ℃;

DOI:10.1021/ma901984d

Reference yield: 83.0%

N-benzhydryl azetidine (107128-00-7) → azetidine (503-29-7)

Guidance literature:

With hydrogenchloride; potassium hydroxide; hydrogen; palladium on activated charcoal; 1.) methanol, 60 deg C, 40 - 80 psi, 2 h, 2.) 100 deg C;

upstream raw materials:

3-aminopropyl hydrogen sulfate

1-(toluene-4-sulfonyl)azetidine

Trimethylenediamine

3-chloropropan-1-amine

Downstream raw materials:

Methylen-bis-azetidin

azetidin-2-ylmethanol

1,5-diazacyclooctane

2,4,6-tris-(1'-azetidinyl)-1,3,5-triazine

Refernces

Discovery of a novel azetidine scaffold for colony stimulating factor-1 receptor (CSF-1R) Type II inhibitors by the use of docking models

10.1016/j.bmcl.2018.10.051

The study focuses on identifying a new class of azetidine compounds as selective CSF-1R Type II kinase inhibitors. CSF-1R is a receptor tyrosine kinase involved in the differentiation, proliferation, and survival of monocyte-macrophage lineage cells, and its inhibition is considered therapeutic for conditions like rheumatoid arthritis. The researchers used structure-based drug design, guided by docking models, to develop these azetidine compounds. They synthesized various azetidine analogues, such as compounds 1a-d, 2a-b, and 3a-b, to explore the optimal binding configurations. The study identified compound 4a, with a CSF-1R inhibitory activity of IC50 = 9.1 nM, as a potent inhibitor. The researchers also obtained a co-crystal structure of an azetidine compound with CSF-1R, confirming that these compounds bind to the DFG-out conformation of the protein as Type II inhibitors. This work highlights the potential of azetidine scaffolds for developing selective and potent CSF-1R inhibitors.