4-oxoazetidin-2-yl acetate

• ChemBase ID: 68706
• Molecular Formular: C5H7NO3
• Molecular Mass: 129.11398
• Monoisotopic Mass: 129.04259309
• SMILES: N1C(=O)CC1OC(=O)C
• Canonical SMILES: O=C1CC(N1)OC(=O)C
• InChI: InChI=1S/C5H7NO3/c1-3(7)9-5-2-4(8)6-5/h5H,2H2,1H3,(H,6,8)
• InChIKey: OEYMQQDJCUHKQS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxoazetidin-2-yl acetate
• IUPAC Traditional name: 4-oxoazetidin-2-yl acetate
• Synonyms: 4-Acetoxy-2-azetidinone; 4-Acetoxy-2-azetidinone; 4-乙酰氧基-2-氮杂环丁酮

Database IDs

• CAS Number: 28562-53-0
• EC Number: 249-083-7
• MDL Number: MFCD00010593
• Beilstein Number: 1524738
• PubChem SID: 162034436; 24856456
• PubChem CID: 119981

CALCULATED PROPERTIES

• Acid pKa: 10.277145
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.79137546
• LogD (pH = 7.4): -0.79187924
• Log P: -0.791369
• Molar Refractivity: 27.6843 cm^3
• Polarizability: 11.329346 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 38-40 °C(lit.); 39-41 °C
• Flash Point: 110 °C; 230 °F

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Corrosive (C)
• UN Number: 1759
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34-43
• Safety Statements: 26-36/37/39-45
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H334
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1759 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (GC); 95+%; 97%; 98%
• Grade: puriss.
• Empirical Formula (Hill Notation): C5H7NO3

DETAILS

Sigma Aldrich - 272159

Packaging
1, 5 g in glass bottle
Application
Useful heterocyclic synthon1 for antibiotic2 and anti-inflammatory3 agents.

Sigma Aldrich - 00810

Other Notes
Building block for the synthesis of β-substituted β-lactams; reaction with carbon nucleophiles1,2; Synthesis of ethers3