CAS 28562-53-0 4-Acetoxy-2-azetidinone (HCID 119981)

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Basic information

CAS: 28562-53-0
Standard SMILES: CC(=O)OC1CC(=O)N1
InChIKey: OEYMQQDJCUHKQS-UHFFFAOYSA-N
Molecular formula: C5H7NO3
Average molar mass: 129.11 g/mol
Monoisotopic mass: 129.04259309

Names & identifiers

Preferred name: 4-Acetoxy-2-azetidinone
IUPAC: (4-oxoazetidin-2-yl) acetate
English name: 4-Acetoxy-2-azetidinone
Molecular formula: C5H7NO3
Molecular weight: 129.11

Names & synonyms

4-Acetoxy-2-azetidinone28562-53-02-Oxoazetidinium 4-acetateRefChem:477770249-083-74-oxoazetidin-2-yl acetate2-Azetidinone, 4-(acetyloxy)-(4-oxoazetidin-2-yl) acetateMFCD000105934-acetoxyazetidinone4-acetoxyazetidin-2-one4-Oxo-2-azetidinyl acetate

Show more names

3-Acetoxy-3-propanelactam4-Acetyloxyazetidin-2-one4-OXOAZETIDIN-2-YLACETATE4-ACETOXY-2-AZETIDINONE(4-AA)4-Acetoxy-2-azetidinone - [A15221]Acetic acid 4-oxo-2-azetidinyl ester

4-Hydroxy-2,3-dihydroazet-2-yl acetateEINECS 249-083-74-acetoxy-azetidinone4-acetoxyazetidine-2-one4-Oxo-2-azetidinyl acetate #CHEMBL122408SCHEMBL1220023SCHEMBL5405424

Database identifiers

CAS: 28562-53-0
PubChem CID: 119981
ChEMBL: CHEMBL122408
EC Number: 249-083-7
Nikkaji: J250.737D

Properties

Computed structural properties

XLogP: -0.3
Topological polar surface area: 55.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 9
Formal charge: 0
Complexity: 154

Physicochemical properties

Melting point: 38 · 38-40 °C (lit.)
Boiling point: 239.15 °C · 239.15°C (rough estimate)
Density: 1.3816 · 1.3816 (rough estimate)
refractive index: 1.422 · 1.4220 (estimate)
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
solubility: 50 mg/mL, · formic acid: soluble50mg/mL, clear, yellow-orange
pka: 13.41 · 13.41±0.40(Predicted)
form: solid
Appearance: Light yellow to orange Solid
BRN: 1524738 · 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 · 28562-53-0(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H334 (97.6%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

P233, P260, P264, P271, P280, P284, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P342+P316, P363, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Corr. 1B (100%)；Resp. Sens. 1 (97.6%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
ridadr: UN 1759 8/PG 2
risk_code: 34-43
Signal word: Danger
Symbol(GHS): GHS05,GHS08
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III

Chemistry & industry

Applications

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.