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Acetolactone

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Acetolactone
Structural formula
Structural formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name Oxiran-2-one
Preferred IUPAC name Oxiranone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H2O2/c3-2-1-4-2/h1H2Key: HZSIFDFXFAXICF-UHFFFAOYSA-N
  • InChI=1/C2H2O2/c3-2-1-4-2/h1H2Key: HZSIFDFXFAXICF-UHFFFAOYAQ
SMILES
  • O=C1OC1
Properties
Chemical formula C2H2O2
Molar mass 58.036 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Acetolactone (α-acetolactone) is an organic compound with formula C
2H
2O
2. It is the smallest member of the lactone family but can also be described as the epoxide of ethenone. The compound was described in 1997 as a transient species in mass spectrometry experiments.

Although acetolactone itself has not been isolated in bulk, the related species bis(trifluoromethyl)acetolactone ((CF
3)
2C
2O
2), which has increased electronic stabilisation due to its two trifluoromethyl groups, is known and has a half-life of 8 hours at 25 °C. This compound is prepared by photolysis of bis(trifluoromethyl)malonyl peroxide.

See also

References

  1. "Acetolactone". PubChem. National Center for Biotechnology Information.
  2. Detlef Schröder, Norman Goldberg, Waltraud Zummack, Helmut Schwarz, John C. Poutsma and Robert R. Squires (1997), Generation of α-acetolactone and the acetoxyl diradical •CH2COO• in the gas phase. International Journal of Mass Spectrometry and Ion Processes, volumes 165-166, November issue, pages 71-82. doi:10.1016/S0168-1176(97)00150-X
  3. Waldemar Adam, Ju-Chao Liu, Oswaldo Rodriguez (1973), Bis(trifluoromethyl)acetolactone, a Stable α-Lactone. J. Org. Chem., volume 38, pages 2269–2270 doi:10.1021/jo00952a047


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