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272159

Sigma-Aldrich

4-Acetoxy-2-azetidinone

98%

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About This Item

Empirical Formula (Hill Notation):
C5H7NO3
CAS Number:
28562-53-0
Molecular Weight:
129.11
Beilstein:
1524738
EC Number:
249-083-7
MDL number:
MFCD00010593
UNSPSC Code:
12352100
PubChem Substance ID:
24856456
NACRES:
NA.22

Assay

98%

form

solid

mp

38-40 °C (lit.)

solubility

formic acid: soluble 50 mg/mL, clear, yellow-orange

storage temp.

2-8°C

SMILES string

CC(=O)OC1CC(=O)N1

InChI

1S/C5H7NO3/c1-3(7)9-5-2-4(8)6-5/h5H,2H2,1H3,(H,6,8)

InChI key

OEYMQQDJCUHKQS-UHFFFAOYSA-N

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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.

Pictograms

Health hazardCorrosion
GHS08,GHS05

Signal Word

Danger

Hazard Statements

H314,H334

Hazard Classifications

Resp. Sens. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBZ4011V
MKBV7888V
MKBV0798V
MKBD7479
MKBB6021

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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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