272159
4-Acetoxy-2-azetidinone
98%
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About This Item
Empirical Formula (Hill Notation):
C5H7NO3
CAS Number:
Molecular Weight:
129.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
249-083-7
Beilstein/REAXYS Number:
1524738
MDL number:
Assay:
98%
Form:
solid
InChI key
OEYMQQDJCUHKQS-UHFFFAOYSA-N
InChI
1S/C5H7NO3/c1-3(7)9-5-2-4(8)6-5/h5H,2H2,1H3,(H,6,8)
SMILES string
CC(=O)OC1CC(=O)N1
assay
98%
form
solid
mp
38-40 °C (lit.)
solubility
formic acid: soluble 50 mg/mL, clear, yellow-orange
storage temp.
2-8°C
Application
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.
signalword
Danger
hcodes
Hazard Classifications
Resp. Sens. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Regulatory Information
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Journal of the Chemical Society. Perkin Transactions 1, 1235-1235 (1991)
Tetrahedron, 46, 2255-2255 (1990)
Aldrichimica Acta, 18, 95-95 (1985)
Cara Cesario et al.
Organic letters, 11(6), 1293-1295 (2009-02-17)
Acylnitroso-derived hetero-Diels-Alder cycloadducts are susceptible to C-O bond cleavage with Pd(0) and InI to form allylic indium(III) species. The in situ prepared allylindium compounds readily react at room temperature with Eschenmoser's salt. Allylation of 4-acetoxy-2-azetidinone provides derivatized cyclopentenes in high
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