4-Acetoxy-2-azetidinone

4-Acetoxy-2-azetidinone
  • CAS No.:28562-53-0
Other grades of this product :
4-Acetoxy-2-azetidinone Basic information
Product Name:4-Acetoxy-2-azetidinone
Synonyms:2-Azetidinone, 4-(acetyloxy)-;4-Oxo-2-azetidinyl acetate;4-ACETOXY-2-AZETIDINONE;3-Acetoxy-3-propanelactam;2-oxoazetidinium 4-acetate;4-OXOAZETIDIN-2-YLACETATE;4-ACETOXY-2-AZETIDINONE(4-AA);4-Acetyloxyazetidin-2-one
CAS:28562-53-0
MF:C5H7NO3
MW:129.11
EINECS:249-083-7
Product Categories:Carbonyl Compounds;Lactams;Ring Systems;Organic Building Blocks
Mol File:28562-53-0.mol
4-Acetoxy-2-azetidinone Chemical Properties
Melting point 38-40 °C (lit.)
Boiling point 239.15°C (rough estimate)
density 1.3816 (rough estimate)
refractive index 1.4220 (estimate)
Fp >230 °F
storage temp. 2-8°C
solubility formic acid: soluble50mg/mL, clear, yellow-orange
pka13.41±0.40(Predicted)
BRN 1524738
CAS DataBase Reference28562-53-0(CAS DataBase Reference)
NIST Chemistry Reference4-Acetoxy-2-azetidinone(28562-53-0)
Safety Information
Hazard Codes C
Risk Statements 34-43
Safety Statements 26-36/37/39-45
RIDADR UN 1759 8/PG 2
WGK Germany 3
HazardClass 8
PackingGroup III
MSDS Information
ProviderLanguage
SigmaAldrich English
4-Acetoxy-2-azetidinone Usage And Synthesis
Chemical PropertiesWhite crystalline powder
Uses4-Acetoxy-2-azetidinone was used in the synthesis of derivatized cyclopentenes in high regio- and diastereoselectivity. It was also used as a heterocyclic synthon for antibiotic and anti-inflammatory agents.
Synthesis Reference(s)Journal of the American Chemical Society, 112, p. 7820, 1990 DOI: 10.1021/ja00177a067Tetrahedron Letters, 29, p. 1409, 1988 DOI: 10.1016/S0040-4039(00)80310-X
Purification MethodsDissolve it in CHCl3, dry (MgSO4) concentrate at 40o/70mm, or better at room temperature to avoid decomposition. Wash and stir the residual oil with hexane by decantation and discard the wash. Dry the oil at high vacuum when it should solidify, m 34o. It can be distilled at high vacuum, 80-82o/10-3mm, but this results in extensive losses. The purity can be checked by TLC using Merck Silica Gel F254 and eluting with EtOAc. The azetidinone has RF 0.38 (typical impurities have RF 0.67). The spots can be detected by the TDM spray. This is prepared from (A) 2.5g 4,4'-tetramethyldiaminodiphenylmethane (TDM) in 10mL AcOH and diluted with 50mL of H2O, (B) 5g KI in 100mL of H2O and (C) 0.3g ninhydrin in 10mL of AcOH and 90mL of H2O. The spray is prepared by mixing (A) and (B) with 1.5mL of (C) and stored in a brown bottle. [Clau et al. Justus Liebigs Ann Chem 539 1974, Michel et al. Org Synth 65 135 1987, Beilstein 21/12 V 4.]

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