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2-Piperidinone

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2-Piperidinone
Names
Preferred IUPAC name Piperidin-2-one
Other names
  • δ-Valerolactam
  • 2-Piperidinone
  • 2-Piperidone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.567 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NO/c7-5-3-1-2-4-6-5/h1-4H2,(H,6,7)Key: XUWHAWMETYGRKB-UHFFFAOYSA-N
  • InChI=1/C5H9NO/c7-5-3-1-2-4-6-5/h1-4H2,(H,6,7)Key: XUWHAWMETYGRKB-UHFFFAOYAE
SMILES
  • O=C1NCCCC1
Properties
Chemical formula C5H9NO
Molar mass 99.133 g·mol
Density 1.073 g/cm
Melting point 38 to 40 °C (100 to 104 °F; 311 to 313 K)
Boiling point 256 °C (493 °F; 529 K)
Solubility in water 291 g/L
Hazards
Flash point > 110 °C (230 °F; 383 K)
Safety data sheet (SDS) MSDS
Related compounds
Related compounds 4-Piperidinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2-Piperidinone (2-piperidone or δ-valerolactam) is an organic compound with the formula (CH2)4CONH. Valerolactam is formed by dehydrogenation of 5-amino-1-pentanol, catalyzed by rhodium and ruthenium complexes, The compound, a colorless solid, is classified as a lactam.

It is the monomer of nylon 5, a polyamide:

n (CH2)4CONH → [HN(CH2)4CO)]n

References

  1. ^ 2-Piperidone at Chemical Book
  2. ^ δ-Valerolactam at Sigma-Aldrich
  3. M. Trincado; K. Kühlein; H. Grützmacher (2011), "Metal-Ligand Cooperation in the Catalytic Dehydrogenative Coupling (DHC) of Polyalcohols to Carboxylic Acid Derivatives", Chem. Eur. J., 17 (42): 11905–11913, doi:10.1002/chem.201101084, PMID 21901769
  4. D. Pingen; D. Vogt (2014), "Amino-Alcohol Cyclization: Selective Synthesis of Lactams and Cyclic Amines from Amino-Alcohols", Catal. Sci. Technol., 4: 47–52, doi:10.1039/C3CY00513E, hdl:20.500.11820/6875ce86-a727-49b8-949f-f71a172043a3, S2CID 52265163
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