Azetidine

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title: "Azetidine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["azetidines"] topic_path: "general/azetidines" source: "https://en.wikipedia.org/wiki/Azetidine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443410972 | ImageFileL1 = Azetidine structure.svg | ImageSizeL1 = 100px | ImageFileR1 = Azetidine3d.png | ImageSizeR1 = 100px | PIN= Azetidine | SystematicName = Azacyclobutane | OtherNames = Azetane Trimethylene imine 1,3-Propylenimine |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 9993 | InChI = 1/C3H7N/c1-2-4-3-1/h4H,1-3H2 | InChIKey = HONIICLYMWZJFZ-UHFFFAOYAE | StdInChI_Ref = | StdInChI = 1S/C3H7N/c1-2-4-3-1/h4H,1-3H2 | StdInChIKey_Ref = | StdInChIKey = HONIICLYMWZJFZ-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 503-29-7 | ChEMBL_Ref = | ChEMBL = 2171713 | PubChem = 10422 | ChEBI_Ref = | ChEBI = 30968 | EC_number = 207-963-8 | UNII = 37S883XDWR | Gmelin = 986 | Beilstein = 102384 | SMILES = N1CCC1 |Section2={{Chembox Properties | Formula = | C=3 | H=7 | N=1 | MolarMass = 57.09 g/mol | Appearance = colorless liquid | Density = 0.847 g/cm3 at 25 °C | MeltingPt = | BoilingPtC = 61 to 62 | BoilingPt_notes = | pKa = 11.29 (conjugate acid; H2O) | Solubility = miscible |Section3={{Chembox Hazards | MainHazards = Somewhat strong base, combustible | FlashPt = | AutoignitionPt = | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = |Section8={{Chembox Related | OtherCompounds = Aziridine, Diazetidine, Pyrrolidine, Piperidine, Azepane, Azocane, Azonane | OtherAnions = Oxetane, Phosphetane, Thietane

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.

Synthesis and occurrence

::figure[src="https://upload.wikimedia.org/wikipedia/commons/d/df/MugineicAcid.svg" caption="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". Azetidine can also be produced by a multistep route from 3-amino-1-propanol.

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.

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.

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
  3. (2007). "Β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products". Chemical Reviews.
  4. Donald H. Wadsworth. (1973). "Azetidine". Organic Syntheses.
  5. (Aug 10, 2020). "Regio- and Diastereoselective Synthesis of 2-Arylazetidines. Quantum Chemical Explanation of Baldwin's Rules for the Ring-formation Reactions of Oxiranes.". Journal of Organic Chemistry.

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azetidines