328464
2-Azetidinone
98%
Synonym(s):
β-Propiolactam, 2-Azacyclobutanone
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About This Item
Empirical Formula (Hill Notation):
C3H5NO
CAS Number:
Molecular Weight:
71.08
Beilstein:
104563
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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