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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)

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 (pK_a)

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).

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Infobox references

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.

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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]}

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]

References

^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 147. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
^ Alcaide, Benito; Almendros, Pedro; Aragoncillo, Cristina (2007). "Β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products". Chemical Reviews. 107 (11): 4437–4492. doi:10.1021/cr0307300. PMID 17649981.
^ Donald H. Wadsworth (1973). "Azetidine". Organic Syntheses. 53: 13. doi:10.15227/orgsyn.053.0013.
^ Kovács, Ervin; Ferenc, Faigl; Zoltan, Mucsi (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. 85 (17): 11226–11239. doi:10.1021/acs.joc.0c01310. PMC 7498157. PMID 32786621.

External links

ChemSynthesis

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This page was last edited on 6 August 2022, at 11:45