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328464

Sigma-Aldrich

2-Azetidinone

98%

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Synonym(s):
β-Propiolactam, 2-Azacyclobutanone
Empirical Formula (Hill Notation):
C3H5NO
CAS Number:
930-21-2
Molecular Weight:
71.08
Beilstein:
104563
MDL number:
MFCD00013328
UNSPSC Code:
12352100
PubChem Substance ID:
24859374
NACRES:
NA.22

Quality Level

100

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
Investigation of the molecular structure and VUV-induced ion dissociation dynamics of 2-azetidinone (C3 H5 NO).
Alexsandre F Lago et al.
Rapid communications in mass spectrometry : RCM, 35(3), e8988-e8988 (2020-10-24)
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
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