# Azetidine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Azetidine
> Markdown URL: https://mediated.wiki/source/Azetidine.md
> Source: https://en.wikipedia.org/wiki/Azetidine
> Source revision: 1347678449
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{distinguish|azatadine}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443410972
| ImageFileL1 = Azetidine structure.svg
| ImageSizeL1 = 100px
| ImageFileR1 = Azetidine3d.png
| ImageSizeR1 = 100px
| PIN= Azetidine<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [The Royal Society of Chemistry](/source/Royal_Society_of_Chemistry) | date = 2014 | location = Cambridge | page = 147 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
| SystematicName = Azacyclobutane
| OtherNames = Azetane<br />Trimethylene imine<br />1,3-Propylenimine
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9993
| InChI = 1/C3H7N/c1-2-4-3-1/h4H,1-3H2
| InChIKey = HONIICLYMWZJFZ-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H7N/c1-2-4-3-1/h4H,1-3H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HONIICLYMWZJFZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 503-29-7
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2171713
| PubChem = 10422
| ChEBI_Ref = {{ebicite|correct|EBI}}
| 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/cm<sup>3</sup> at 25 °C
| MeltingPt = 
| BoilingPtC = 61 to 62
| BoilingPt_notes = 
| pKa = 11.29 (conjugate acid; H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = [CRC Press](/source/CRC_Press) | isbn = 978-1498754286 | pages=5–89 | title-link = CRC Handbook of Chemistry and Physics }}</ref>
| Solubility = miscible
  }}
|Section3={{Chembox Hazards
| MainHazards = Somewhat strong base, combustible 
| FlashPt = 
| AutoignitionPt = 
| GHSPictograms = {{GHS02}}{{GHS05}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|314}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|370+378|403+235|405|501}}
 }}
|Section8={{Chembox Related
| OtherCompounds = [Aziridine](/source/Aziridine), [Diazetidine](/source/Diazetidine), [Pyrrolidine](/source/Pyrrolidine), [Piperidine](/source/Piperidine), [Azepane](/source/Azepane), [Azocane](/source/Azocane), [Azonane](/source/Azonane)
| OtherAnions = [Oxetane](/source/Oxetane), [Phosphetane](/source/Phosphetane), [Thietane](/source/Thietane)
 }}
}}

'''Azetidine''' is a [saturated](/source/Saturated_and_unsaturated_compounds) [heterocyclic](/source/heterocyclic) [organic compound](/source/organic_compound) containing three [carbon](/source/carbon) atoms and one [nitrogen](/source/nitrogen) atom. It is a liquid at room temperature with a strong odor of ammonia and is strongly [basic](/source/Base_(chemistry)) compared to most secondary amines.

==Synthesis and occurrence==
[[File:MugineicAcid.svg|thumb|left|220px|[Mugineic acid](/source/Mugineic_acid), an [iron-binding](/source/siderophore) azetidine.]]
Azetidines can be prepared by reduction of [azetidinone](/source/azetidinone)s (β-lactams) with [lithium aluminium hydride](/source/lithium_aluminium_hydride). Even more effective is a mixture of lithium aluminium hydride and [aluminium trichloride](/source/aluminium_trichloride), a source of "AlClH<sub>2</sub>" and "AlCl<sub>2</sub>H".<ref>{{cite journal |doi=10.1021/cr0307300 |title=Β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products |year=2007 |last1=Alcaide |first1=Benito |last2=Almendros |first2=Pedro |last3=Aragoncillo |first3=Cristina |journal=Chemical Reviews |volume=107 |issue=11 |pages=4437–4492 |pmid=17649981}}</ref> 

Azetidine can also be produced by a multistep route from 1,3-disubstituted alkanes.  Thus, for example, a multistep route builds azetidine from [3-amino-1-propanol](/source/3-Amino-1-propanol), [acrylic acid](/source/acrylic_acid), [thionyl chloride](/source/thionyl_chloride), and base;<ref>{{cite journal |doi=10.15227/orgsyn.053.0013 |title=Azetidine |journal=Organic Syntheses |year=1973 |volume=53 |page=13 |author=Donald H. Wadsworth}}</ref> likewise, azetidine dicarboxylic acids form when [glutaric anhydride](/source/glutaric_anhydride) is brominated (at the α position) and then aminated.<ref>{{cite journal|doi=10.1021/jm00168a007|title=Synthesis and bioactivity of a new class of rigid glutamate analogues|first1=Alan P.|last1=Kozikowski|first2=Werner|last2=Tückmantel|first3=Ian J.|last3=Reynolds|first4=Jarda T.|last4=Wroblewski|year=1990|publisher=American Chemical Society|journal=Journal of Medicinal Chemistry|volume=33|issue=6|p=1563}}</ref>

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.<ref>{{cite journal |last1=Kovács |first1=Ervin |last2=Ferenc |first2=Faigl |last3=Zoltan |first3=Mucsi |title=Regio- and Diastereoselective Synthesis of 2-Arylazetidines. Quantum Chemical Explanation of Baldwin's Rules for the Ring-formation Reactions of Oxiranes. |journal=Journal of Organic Chemistry |date=Aug 10, 2020 |volume=85 |issue=17 |pages=11226–11239 |doi=10.1021/acs.joc.0c01310|pmid=32786621 | pmc=7498157 |doi-access=free }}</ref>

The [Paternò−Büchi reaction](/source/Patern%C3%B2%E2%88%92B%C3%BCchi_reaction) has [an ''aza'' analogue](/source/Aza_Patern%C3%B2%E2%88%92B%C3%BCchi_reaction).  

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](/source/azetidine-2-carboxylic_acid) - a toxic mimic of [proline](/source/proline).{{cn|date=February 2021}}

== See also ==
* [Azete](/source/Azete), the unsaturated analog

==References==
{{Reflist}}

==External links==
* [http://www.chemsynthesis.com/base/chemical-structure-13241.html ChemSynthesis]

Category:Azetidines

---
Adapted from the Wikipedia article [Azetidine](https://en.wikipedia.org/wiki/Azetidine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Azetidine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.