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130036

Sigma-Aldrich

N-Methyl-4-piperidone

97%

Sinónimos:

1-Methyl-4-piperidinone

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About This Item

Fórmula empírica (notación de Hill):
C6H11NO
Número de CAS:
1445-73-4
Peso molecular:
113.16
Beilstein/REAXYS Number:
106924
EC Number:
215-895-5
MDL number:
MFCD00006191
UNSPSC Code:
12352100
PubChem Substance ID:
24847937
NACRES:
NA.22

reg. compliance

suitable for FDA C-010.02

assay

97%

form

liquid

density

0.92 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CN1CCC(=O)CC1

InChI

1S/C6H11NO/c1-7-4-2-6(8)3-5-7/h2-5H2,1H3

InChI key

HUUPVABNAQUEJW-UHFFFAOYSA-N

Application

N-Methyl-4-piperidone can be used as a reactant to prepare:
  • Spiropiperidine rings by reacting with malononitrile and electrophiles or Michael acceptors.
  • (3E,5E)-1-Methyl-3,5-bis(phenylmethylene)-4-piperidinone by reacting with benzaldehyde via Michael addition, followed by intramolecular O-cyclization/elimination sequential reactions.
  • N,N′-Dimethylbispidinone by utilizing a double Mannich condensation method.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

136.4 °F - closed cup

flash_point_c

58 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificados de análisis (COA)

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Analogs of sparteine. I. Reexamination of the reaction of N-methyl-4-piperidone with formaldehyde and methylamine. Revised synthesis of N, N'-dimethylbispidinone
Smissman EE, et al.
The Journal of Organic Chemistry, 40, 251-252 (1975)
Analogs of sparteine. I. A reexamination of the reaction of n-methyl-4-piperidone with formaldehyde and methylamine. A revised synthesis of n,n'-dimethylbispidinone.
E E Smissman et al.
The Journal of organic chemistry, 40(2), 251-252 (1975-01-24)
A facile tandem Michael addition/O-cyclization/elimination route to novel chromeno [3, 2-c] pyridines
Sumesh RV, et al.
Molecular Diversity, 19, 233-249 (2015)
Novel route to spiropiperidines using N-methyl-4-piperidone, malononitrile and electrophiles
Lakshmi NV, et al.
Tetrahedron Letters, 53, 1282-1286 (2012)
Bin-Rong Yao et al.
European journal of medicinal chemistry, 167, 187-199 (2019-02-17)
To get new anti-hepatoma agents with anti-inflammatory activity and hypotoxicity, a series of dissymmetric pyridyl-substituted 3,5-bis(arylidene)-4-piperidones (BAPs, 25-82) were designed and synthesized. Many of them exhibited potential anti-hepatoma properties against human hepatocellular carcinoma cell lines (HepG2, QGY-7703, SMMC-7721) and hypotoxicity
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