Azetidine
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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Names | |||
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Preferred IUPAC name
Azetidine[1] | |||
Systematic IUPAC name
Azacyclobutane | |||
Other names
Azetane Trimethylene imine 1,3-Propylenimine | |||
Identifiers | |||
3D model (JSmol) |
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102384 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.240 | ||
EC Number |
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986 | |||
PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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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 | |||
Main hazards | Somewhat strong base, combustible | ||
GHS pictograms | |||
GHS Signal word | Danger | ||
GHS hazard statements |
H225, H314 | ||
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
Infobox references | |||
Synthesis and occurrence
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]
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 homolog of proline.
See also
- Azete, the unsaturated analog
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. p. 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.