Azetidine

Azetidine

Names
Preferred IUPAC name Azetidine
Systematic IUPAC name Azetane
Other names Azacyclobutane Trimethylene imine 1,3-Propylenimine
Identifiers
CAS Number	503-29-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30968 Y
ChEMBL	ChEMBL2171713 N
ChemSpider	9993 Y
ECHA InfoCard	100.007.240
CompTox Dashboard (EPA)	DTXSID8060117
InChI InChI=1S/C3H7N/c1-2-4-3-1/h4H,1-3H2 Y Key: HONIICLYMWZJFZ-UHFFFAOYSA-N Y InChI=1/C3H7N/c1-2-4-3-1/h4H,1-3H2 Key: HONIICLYMWZJFZ-UHFFFAOYAE
SMILES N1CCC1
Properties
Chemical formula	C3H7N
Molar mass	57.09 g/mol
Appearance	Clear slight brown liquid
Density	0.847 g/cm3 at 25 °C
Boiling point	61 to 62 °C (142 to 144 °F; 334 to 335 K)
Solubility in water	miscible
Acidity (pKa)	11.25 (pKa of conjugate acid in water),
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Azetidine is a saturated heterocyclic organic compound containing three carbon atoms and one nitrogen atom. It is a liquid at room temperature with a strong odor of ammonia and is strongly basic compared to most secondary amines. Azetidines do not occur as frequently in nature and have been studied far less than closely related chemical compounds such as pyrrolidine and β-lactam.

Natural occurrence

Azetidine and its derivatives are relatively rare structural motifs in natural products. Notably, they are a key component of mugineic acids and penaresidins. Perhaps the most abundant azetidine containing natural product is azetidine-2-carboxylic acid, a non-proteinogenic homolog of proline.

See also

• Azete, the unsaturated analog

External links

• Pubchem
• ChemSynthesis