Azetidine

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Azetidine
Names
Preferred IUPAC name
Azetidine
Systematic IUPAC name
Azetane
Other names
Azacyclobutane
Trimethylene imine
1,3-Propylenimine
Identifiers
3D model (JSmol)
102384
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.240 Edit this at Wikidata
EC Number
  • 207-963-8
986
UNII
  • InChI=1S/C3H7N/c1-2-4-3-1/h4H,1-3H2 checkY
    Key: HONIICLYMWZJFZ-UHFFFAOYSA-N checkY
  • InChI=1/C3H7N/c1-2-4-3-1/h4H,1-3H2
    Key: HONIICLYMWZJFZ-UHFFFAOYAE
  • N1CCC1
Properties
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)
miscible
Acidity (pKa) 11.25 (pKa of conjugate acid in water),[1]
Hazards
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H225, H314
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

References

  1. ^ Bansal, R.K. "Heterocyclic Chemistry" 3rd Ed. 1999, p. 96

External links


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