Azetidine

Not to be confused with azatadine.

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.

Azetidine

Names
Preferred IUPAC name Azetidine[1]
Systematic IUPAC name Azacyclobutane
Other names Azetane Trimethylene imine 1,3-Propylenimine
Identifiers
CAS Number	503-29-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	102384
ChEBI	CHEBI:30968 Y
ChEMBL	ChEMBL2171713 N
ChemSpider	9993 Y
ECHA InfoCard	100.007.240
EC Number	207-963-8
Gmelin Reference	986
PubChem CID	10422
UNII	37S883XDWR
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	colorless 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)	11.29 (conjugate acid; H2O)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Somewhat strong base, combustible
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H314
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Related compounds
Other anions	Oxetane, Phosphetane, Thietane
Related compounds	Aziridine, Diazetidine, Pyrrolidine, Piperidine, Azepane, Azocane, Azonane
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

Synthesis and occurrence

Mugineic acid, an iron-binding azetidine.

Azetidines can be prepared by reduction of azetidinones (β-lactams) with lithium aluminium hydride. Even more effective is a mixture of lithium aluminium hydride and aluminium trichloride, a source of "AlClH₂" and "AlCl₂H".^[3] Azetidine can also be produced by a multistep route from 3-amino-1-propanol.^[4]

Regio- and diastereoselective synthesis of 2-arylazetidines could be performed from appropriately substituted oxiranes via ring transformation. It is controlled by Baldwin's Rules with remarkable functional group tolerance.^{[citation needed]}

The Paternò−Büchi reaction has an aza analogue.

Azetidine and its derivatives are relatively rare structural motifs in natural products. They are a component of mugineic acids and penaresidins. Perhaps the most abundant azetidine containing natural product is azetidine-2-carboxylic acid - a toxic mimic of proline.^[5]

See also

• Azete, the unsaturated analog