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1,3-Cyclopentanedione

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1,3-Cyclopentanedione
Names
Preferred IUPAC name Cyclopentane-1,3-dione
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1362728
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.021.249 Edit this at Wikidata
EC Number
  • 223-372-8
Gmelin Reference 200797
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H6O2/c6-4-1-2-5(7)3-4/h1-3H2Key: LOGSONSNCYTHPS-UHFFFAOYSA-N
SMILES
  • C1CC(=O)CC1=O
Properties
Appearance white solid
Density 1.37 g/cm
Melting point 149–151 °C (300–304 °F; 422–424 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,3-Cyclopentanedione is an organic compound with the formula (CH2)3(CO)2. It is one of two isomeric cyclopentanediones, the other being 1,2-cyclopentanedione. The enol is predicted to be about 1-3 kcal/mol more stable than the diketo form. The enol structure has been confirmed by X-ray crystallography.

Preparation

The compound is prepared by hydrogenation of 2-cyclopentene-1,4-dione using zinc/acetic acid.

References

  1. Jana, Kalyanashis; Ganguly, Bishwajit (2018). "DFT Study to Explore the Importance of Ring Size and Effect of Solvents on the Keto–Enol Tautomerization Process of α- and β-Cyclodiones". ACS Omega. 3 (7): 8429–8439. doi:10.1021/acsomega.8b01008. PMC 6644555. PMID 31458971.
  2. Katrusiak, A. (1990). "Structure of 1,3-cyclopentanedione". Acta Crystallographica Section C: Crystal Structure Communications. 46 (7): 1289–1293. Bibcode:1990AcCrC..46.1289K. doi:10.1107/S0108270189011352.
  3. McIntosh, John M.; Beaumier, Pierre. (1972). "Improved Preparation of 1,3-cyclopentanedione". The Journal of Organic Chemistry. 37 (18): 2905–2906. doi:10.1021/jo00983a027.
  4. Gary H. Rasmusson; Herbert O. House; Edward F. Zaweski; Charles H. DePuy (1962). "2-Cyclopentene-1,4-Dione". Organic Syntheses. 42: 36. doi:10.15227/orgsyn.042.0036.
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