328464

Sigma-Aldrich

2-Azetidinone

98%

Synonym(s):
2-Azacyclobutanone, β-Propiolactam
Empirical Formula (Hill Notation):
C3H5NO
CAS Number:
Molecular Weight:
71.08
Beilstein/REAXYS Number:
104563
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

bp

106 °C/15 mmHg (lit.)

mp

74-76 °C (lit.)

solubility

chloroform: very soluble(lit.)
ethanol: very slightly soluble(lit.)
water: very soluble(lit.)

storage temp.

2-8°C

SMILES string

O=C1CCN1

InChI

1S/C3H5NO/c5-3-1-2-4-3/h1-2H2,(H,4,5)

InChI key

MNFORVFSTILPAW-UHFFFAOYSA-N

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General description

2-Azetidinone is an unsubstituted four membered lactam. 2-Azetidinone is the fundamental building block of β-lactam antibiotics. X-ray photoelectron spectra of 2-azetidinone was investigated. 2-Azetidinone undergoes hydrolysis with aqueous alkali to yield β-alanine.

Application

2-Azetidinone was used in synthesis of optically pure densely functionalized γ-lactams.

Packaging

1, 5 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3263 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

2-Azetidinone (?-propiolactam)
Holley RW and Holley AD.
Journal of the American Chemical Society, 71(6), 2129-2131 (1949)
Benito Alcaide et al.
The Journal of organic chemistry, 69(3), 993-996 (2004-01-31)
A synthesis of optically pure densely functionalized gamma-lactams starting from 2-azetidinone-tethered iminophosphoranes has been developed. Full chirality transfer has been accomplished from the enantiomerically pure 2-azetidinones. The addition of lithium acetylides to 4-oxoazetidine-2-carbaldehydes at -78 degrees C smoothly yielded propargylic...
Marawan Ahmed et al.
The journal of physical chemistry. A, 116(33), 8653-8660 (2012-07-18)
X-ray photoelectron spectra of the core and valence levels of the fundamental building blocks of β-lactam antibiotics have been investigated and compared with theoretical calculations. The spectra of the compounds 2-azetidinone and the 2- and 4-isomers of thiazolidine-carboxylic acid are...
Tim N Beck et al.
Bioorganic & medicinal chemistry, 23(3), 632-647 (2015-01-01)
The prevalence of drug resistance in both clinical and community settings as a consequence of alterations of biosynthetic pathways, enzymes or cell wall architecture is a persistent threat to human health. We have designed, synthesized, and tested a novel class...
Dariusz Suchy et al.
Naunyn-Schmiedeberg's archives of pharmacology, 387(8), 733-742 (2014-05-02)
Macrophages are crucial for the development of atherosclerotic plaques. Classically activated macrophages contribute to plaque growth and destabilization, while alternatively activated macrophages increase plaque stability. Here, we assessed the influence of ezetimibe on the activation of monocyte-derived macrophages isolated from...

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