Structure via PubChem · Public domain (PubChem)
propiolactone
Sign in to saveAlso known as BPL, hydroacrylic acid, β-lactone, 3-hydroxy-β-lactone, 3-hydroxy-propionic acid, 2-oxetanone, 3-propiolactone, β-propiolactone
β-Propiolactone, often simply called propiolactone, is an organic compound with the formula . It is a member of the lactone family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and organic solvents. The carcinogenicity of this compound has limited its commercial applications.
Chemical data
- Formula
- C3H4O2
- Molecular weight
- 72.06 g/mol
- IUPAC name
- oxetan-2-one
- SMILES
- C1COC1=O
- InChIKey
- VEZXCJBBBCKRPI-UHFFFAOYSA-N
- XLogP
- -0.2
- Polar surface area
- 26.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
909 papers- β-Propiolactone, its application and assay methods.Analytical methods : advancing methods and applications · 2025
- beta-Propiolactone.IARC monographs on the evaluation of carcinogenic risks to humans · 1999
- β-Propiolactone (BPL)-inactivation of SARS-Co-V-2: In vitro validation with focus on saliva from COVID-19 patients for scent dog training.Journal of virological methods · 2023
- Carcinogenesis of β-Propiolactone: A Computational Study.Chemical research in toxicology · 2020
- The genetic properties of beta-propiolactone.Mutation research · 1977
via PubMed
Wikidata facts
- Mass
- 72.021129
Show 16 more facts
- melting point
- -33.4
- chemical formula
- C₃H₄O₂
- NIOSH Pocket Guide ID
- 0528
- density
- 1.15
- decomposition point
- 323
- vapor pressure
- 3
- flash point
- 165
- solubility
- 37
- lower flammable limit
- 2.9
- ceiling exposure limit
- 0
- canonical SMILES
- C1COC1=O
- World Health Organisation international non-proprietary name
- propiolactone
- Commons category
- Beta-Propiolactone
- electric dipole moment
- 4.18
- ionization energy
- 9.70
- boiling point
- 162
Sources (3)
via Wikidata · CC0
~2 min read
Article
5 sectionsContents
- Production
- Reactions and applications
- Safety
- See also
- References
β-Propiolactone, often simply called propiolactone, is an organic compound with the formula . It is a member of the lactone family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and organic solvents. The carcinogenicity of this compound has limited its commercial applications.
==Production== β-Propiolactone is prepared industrially by the reaction of formaldehyde and ethenone in the presence of aluminium- or zinc chloride as catalyst: