2-Piperidone

2-Piperidone Basic information
Product Name:2-Piperidone
Synonyms:2-Piperidinone for synthesis;2-KETOPIPERIDINE;2-AZACYCLOHEXANONE;5-pentanelactam;5-Pentanolactam;Pentanoic acid, 5-amino-, lactam;Piperidon;Piperidone-2
CAS:675-20-7
MF:C5H9NO
MW:99.13
EINECS:211-622-9
Product Categories:Pharmaceutical Intermediates;Piperidine;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactams;Organic Building Blocks;675-20-7
Mol File:675-20-7.mol
2-Piperidone Structure
2-Piperidone Chemical Properties
Melting point 38-40 °C (lit.)
Boiling point 256 °C (lit.) 81-82 °C/0.1 mmHg (lit.)
density 1.073
refractive index 1.4431 (estimate)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Low Melting Crystalline Mass
color White to yellow to brown
PH4.8 (200g/l, H2O, 20℃)
explosive limit1.5-8.7%(V)
Water Solubility 291 g/L (25 ºC)
Sensitive Hygroscopic
BRN 106434
Stability:Stable under recommended storage conditions., Stable Under Recommended Storage C
InChIKeyXUWHAWMETYGRKB-UHFFFAOYSA-N
CAS DataBase Reference675-20-7(CAS DataBase Reference)
NIST Chemistry Reference2-Piperidinone(675-20-7)
EPA Substance Registry System2-Piperidone (675-20-7)
Safety Information
Hazard Codes Xi
Risk Statements 36/37-36/37/38
Safety Statements 22-24/25-37/39-26-36
WGK Germany 3
RTECS TO0110000
3-10
TSCA Yes
HS Code 29337900
MSDS Information
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2-Piperidone English
ACROS English
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2-Piperidone Usage And Synthesis
Chemical Propertieswhite to yellowish low melting crystalline mass
Usesδ-Valerolactam is a useful synthetic intermediate. It is an intermediate used to synthesize Cenicriviroc (C256550), an experimental drug candidate for the treatment of HIV infection. It is also a starting material for a new route to hexahydrojulolidines, using intramolecular 1,4-cycloaddition.
DefinitionChEBI: 2-Piperidone is a delta-lactam that is piperidine which is substituted by an oxo group at position 2. It has a role as an EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor. It is a member of piperidones and a delta-lactam.
Preparation2-Piperidone can be obtained from cyclopentanone as raw material by a two-step reaction.
Synthesis Reference(s)Journal of the American Chemical Society, 102, p. 7629, 1980 DOI: 10.1021/ja00546a001
Tetrahedron Letters, 28, p. 2829, 1987 DOI: 10.1016/S0040-4039(00)96220-8
The Journal of Organic Chemistry, 21, p. 965, 1956 DOI: 10.1021/jo01115a010
Purification MethodsPurify it by repeated fractional distillation.[Cowley J Org Chem 23 1330 1958, Reppe et al. Justus Liebigs Ann Chem 596 198 1955, IR: Huisgen et al. Chem Ber 90 1437 1957.] The hydrochloride has m 183-184o (from isoPrOH or EtOH/Et2O) [Hurd et al. J Org Chem 17 865 1952], and the oxime has m 122.5o (from pet ether) [Behringer & Meier Justus Liebigs Ann Chem 607 67 1957]. The picrate has m 92-93o. [Beilstein 21 H 239, 21 III/IV 3170, 21/6 V 396.]
3,3-Tetramethyleneglutarimide Buspirone Amylamine N-Methyl-2-pyrrolidone 3-CARBETHOXY-2-PIPERIDONE 2-Piperidone Piperidine TRIAMYLAMINE 3-hydroxypiperidin-2-one 1-METHYL-2-PIPERIDONE Chlorophacinone Diltiazem hydrochloride 1,5-Diaminopentane Propyzamide Cyclohexanone 3,3-Pentamethylene glutarimide Cyclopentanone Laurocapram

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