2-Piperidinone

2-Piperidinone
Names
	Preferred IUPAC name Piperidin-2-one
	Other names δ-Valerolactam; 2-Piperidinone; 2-Piperidone;
Identifiers
CAS Number	675-20-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:77761 ;
ChemSpider	12144;
ECHA InfoCard	100.010.567
PubChem CID	12665;
UNII	WLN0GQQ6EK ;
CompTox Dashboard (EPA)	DTXSID1060976 ;
	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−1
Density	1.073 g/cm3
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 [77 °F], 100 kPa). Infobox references

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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, ^[3]^[4] 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

^ ^a ^b ^c 2-Piperidone at Chemical Book
^ ^a ^b δ-Valerolactam at Sigma-Aldrich
^ 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
^ 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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[chemicalbook-1] 2-Piperidone at Chemical Book

[Aldrich-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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