| Identification | More | [Name]
4-Acetoxy-2-azetidinone | [CAS]
28562-53-0 | [Synonyms]
4-ACETOXY-2-AZETIDINONE
2-Azetidinone, 4-(acetyloxy)-
4-Oxo-2-azetidinyl acetate
2-oxoazetidinium 4-acetate
4-OXOAZETIDIN-2-YLACETATE
4-ACETOXY-2-AZETIDINONE(4-AA)
4-Acetyloxyazetidin-2-one
Acetic acid 2-oxoazetidin-4-yl ester
Acetic acid 4-oxo-2-azetidinyl ester | [EINECS(EC#)]
249-083-7 | [Molecular Formula]
C5H7NO3 | [MDL Number]
MFCD00010593 | [Molecular Weight]
129.11 | [MOL File]
28562-53-0.mol |
| Chemical Properties | Back Directory | [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 | [form ]
solid | [pka]
13.41±0.40(Predicted) | [Appearance]
Light yellow to orange Solid | [BRN ]
1524738 | [InChI]
InChI=1S/C5H7NO3/c1-3(7)9-5-2-4(8)6-5/h5H,2H2,1H3,(H,6,8) | [InChIKey]
OEYMQQDJCUHKQS-UHFFFAOYSA-N | [SMILES]
N1C(OC(C)=O)CC1=O | [CAS DataBase Reference]
28562-53-0(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Acetoxy-2-azetidinone(28562-53-0) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1759 8/PG 2
| [WGK Germany ]
3
| [HazardClass ]
8 | [PackingGroup ]
III | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Resp. Sens. 1
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder | [Uses]
4-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/ja00177a067
Tetrahedron Letters, 29, p. 1409, 1988 DOI: 10.1016/S0040-4039(00)80310-X | [Synthesis]
The reaction of chlorosulfonyl isocyanate (1.0 mL, 11 mmol) with vinyl acetate (5.0 mL, 54 mmol) in anhydrous dichloromethane for 2 h at 0 °C afforded 4-acetoxy-2-azetidinone (Compound 9, 0.50 g, 35% yield). The spectral data of compound 9 was in agreement with the results reported in the literature. | [Purification Methods]
Dissolve 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.] | [References]
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 17, p. 2055 - 2068
[2] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 10, p. 2990 - 2994
[3] Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 5015 - 5021
[4] Synthesis, 1987, # 3, p. 324
[5] Patent: US8859183, 2014, B2. Location in patent: Paragraph 0258-0261 |
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