Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
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.
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
Azetidine[1] | |||
Systematic IUPAC name
Azacyclobutane | |||
Other names
Azetane Trimethylene imine 1,3-Propylenimine | |||
Identifiers | |||
3D model (JSmol) |
|||
102384 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.240 | ||
EC Number |
| ||
986 | |||
PubChem CID |
|||
UNII | |||
CompTox Dashboard (EPA) |
|||
| |||
| |||
Properties | |||
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) | ||
miscible | |||
Acidity (pKa) | 11.29 (conjugate acid; H2O)[2] | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards |
Somewhat strong base, combustible | ||
GHS labelling: | |||
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 | |||
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).
|
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]
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]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.