beta-Propiolactone
Title: b-Propiolactone
CAS Registry Number: 57-57-8
CAS Name: 2-Oxetanone
Additional Names: hydracrylic acid b-lactone; b-propionolactone; propanolide
Manufacturers' Codes: NSC-21626
Trademarks: Betaprone (Forest)
Molecular Formula: C3H4O2
Molecular Weight: 72.06
Percent Composition: C 50.00%, H 5.60%, O 44.41%
Literature References: Prepd by the condensation of ketene with formaldehyde: Küng, US 2356459 (1941). Purification: Gresham, Jansen, US 2602802 (1952 to B. F. Goodrich). Use in Diels-Alder diene synthesis: Gresham et al., J. Am. Chem. Soc. 76, 609 (1954). Review of carcinogenic risk: IARC Monographs 4, 259-269 (1974).
Properties: Liquid. d420 1.1460; d425 1.1420; d2020 1.1490. mp -33.4°. bp760 162° (dec); bp750 150° (dec); bp20 61°; bp10 51°. Flash pt 70°C (158°F). nD20 1.4131; nD25 1.4110. Dipole moment 3.8. Slowly hydrolyzed to hydracrylic acid. Stable when stored at 5° in glass containers. Soly in water: 37% v/v. Misc with alcohol, acetone, ether, chloroform.
Melting point: mp -33.4°
Boiling point: bp760 162° (dec); bp750 150° (dec); bp20 61°; bp10 51°
Flash point: Flash pt 70°C (158°F)
Index of refraction: nD20 1.4131; nD25 1.4110
Density: d420 1.1460; d425 1.1420; d2020 1.1490
CAUTION: Potential symptoms of overexposure are skin irritation, blistering and burns; corneal opacity; frequent urination; dysuria; hematuria. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 264. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-225.
Use: Versatile intermediate in organic synthesis.
Therap-Cat: Disinfectant.
Keywords: Antiseptic/Disinfectant.

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