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Sigma-Aldrich

2-Azetidinone

98%

Synonym(s):

β-Propiolactam, 2-Azacyclobutanone

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About This Item

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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