N-Methyl-4-piperidinol

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CAS:106-52-5
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CAS:106-52-5
Purity:99% Package:5KG;1KG Remarks:C6H13NO

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  • CAS:106-52-5
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  • 1-Methyl-4-piperidinol
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  • 2023-09-21
  • CAS:106-52-5
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  • Purity: 99%
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N-Methyl-4-piperidinol Basic information
Product Name:N-Methyl-4-piperidinol
Synonyms:1-methyl-4-piperidino;1-Methylpiperidinol-(4);4-Piperidinol, 1-methyl-;N-Methylpiperidol;4-HYDROXY-1-METHYLPIPERIDINE;4-HYDROXY-N-METHYLPIPERIDINE;N-METHYL-4-HYDROXY PIPERIDINE;NM4PPOL
CAS:106-52-5
MF:C6H13NO
MW:115.17
EINECS:203-406-8
Product Categories:Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines;PHARMACEUTICAL INTERMEDIATES;Piperidine
Mol File:106-52-5.mol
N-Methyl-4-piperidinol Structure
N-Methyl-4-piperidinol Chemical Properties
Melting point 29-31 °C(lit.)
Boiling point 200 °C(lit.)
density 0.98 g/mL at 20 °C(lit.)
vapor pressure 8.13-11Pa at 25℃
refractive index n20/D 1.479
Fp 190 °F
storage temp. 2-8°C
form Liquid After Melting
pka14.87±0.20(Predicted)
color Clear colorless to brown
Water Solubility MISCIBLE
Sensitive Hygroscopic
BRN 103024
LogP-0.14-0.756 at 25℃
CAS DataBase Reference106-52-5(CAS DataBase Reference)
NIST Chemistry Reference4-Hydroxy-N-methylpiperidine(106-52-5)
EPA Substance Registry System4-Piperidinol, 1-methyl- (106-52-5)
Safety Information
Hazard Codes Xi,C
Risk Statements 37/38-41-36/37/38-34
Safety Statements 26-37/39-45-36/37/39-27
WGK Germany 3
Hazard Note Irritant
TSCA Yes
HS Code 29333999
MSDS Information
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1-Methyl-4-piperidinol English
SigmaAldrich English
ACROS English
ALFA English
N-Methyl-4-piperidinol Usage And Synthesis
Chemical Propertiesclear colorless to yellowish liquid after melting
UsesReactant for:• ;Optimization of Novobiocin scaffold to product antitumor agents1• ;Substitution about the rigidifying ring for histamine H4 receptor antagonist synthesis2Reactant for synthesis of:• ;CaMKII inhibitors3• ;VEGFR and FGFR kinase inhibitors4• ;Phosphoinositide-3-kinase inhibitors5• ;Protein lysine methyltransferase G9a inhibitors6
Uses4-Hydroxy-1-methylpiperidine is used as reactant for optimization of Novobiocin scaffold to product antitumor agents, substitution about the rigidifying ring for histamine H4 receptor antagonist synthesis. It is also used as a reactant in the synthesis of CaMKII, VEGFR and FGFR kinase inhibitors and Phosphoinositide-3-kinase, Protein lysine methyltransferase G9a inhibitors.
Flammability and ExplosibilityNot classified
Synthesis
1-Methyl-4-piperidone

1445-73-4

N-Methyl-4-piperidinol

106-52-5

The general procedure for the synthesis of 1-methyl-4-piperidinol from N-methyl-4-piperidone was as follows: in standard experiments, the catalyst complex 1 (6.1 mg, 10 mol%) and the hydrogenation reagent H[BAr'4]-(Et2O)2 (10.1 mg, 10 mol%) were dissolved in a 100 mL thick-walled glass reactor fitted with a TEFLON stopper and stirring bar of THF (2.0 mL). Subsequently, the substrate to be hydrogenated (0.5 mmol) was added. The reaction system was degassed by a freeze-pump-thaw cycle and then charged with hydrogen (1 or 4 atm). The reaction mixture was stirred at a set temperature (25-60 °C) until the reaction was complete. At the end of the reaction, the solvent was removed by evaporation and the residue was initially purified by passing through a silica gel column. After removal of solvent under reduced pressure, the crude product was dissolved in CDCl3 and analyzed by 1H NMR. The final product was further purified by column chromatography or preparative thin layer chromatography (TLC) using hexane/ethyl acetate (3:1, v/v) as eluent. The purified products were characterized by 1H NMR and GC-MS, and the spectral data were consistent with those reported in the literature or real samples.

References[1] Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2474 - 2481
[2] Patent: US2015/336862, 2015, A1. Location in patent: Paragraph 0038; 0054
[3] Patent: US2767190, 1950,
[4] Patent: US2776293, 1950,
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 1826
Tag:N-Methyl-4-piperidinol(106-52-5) Related Product Information
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