1-Methyl-4-piperidone
[CAS# 1445-73-4]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1-Methyl-4-piperidone
• Synonyms: 1-Methyltetrahydropyridin-4(1H)-one-; N-Methyl-4-piperidone
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• CAS Registry Number: 1445-73-4
• EC Number: 215-895-5
• SMILES: CN1CCC(=O)CC1

Properties

• Density: 0.98
• Boiling point: 55-58 °C (10 mmHg)
• Refractive index: 1.46-1.462
• Flash point: 58 °C
• Water solubility: MISCIBLE

Safety Data

• Hazard Symbols: GHS02 Warning
• Risk Statements: H226
• Safety Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 1224

Discovery and Applications

1-Methyl-4-piperidone, also known as N-methyl-4-piperidone, is a cyclic amine with a five-membered ring structure that contains a nitrogen atom. It is classified as a piperidone, which refers to the presence of a ketone functional group attached to the piperidine ring. The compound has garnered attention due to its unique chemical properties and versatile applications across various fields.

The discovery of 1-methyl-4-piperidone dates back to the mid-20th century, when chemists began exploring piperidone derivatives for their potential use in pharmaceuticals and organic synthesis. Its structural characteristics were determined through various analytical techniques, including nuclear magnetic resonance (NMR) and mass spectrometry (MS), which helped elucidate its chemical behavior and reactivity.

One of the primary applications of 1-methyl-4-piperidone is as a building block in organic synthesis. It serves as an important intermediate in the preparation of numerous pharmaceuticals, agrochemicals, and fine chemicals. Its ability to undergo various reactions, including nucleophilic substitution and acylation, makes it a valuable precursor in the synthesis of complex molecules. Additionally, 1-methyl-4-piperidone can be employed in the production of heterocyclic compounds, which are of significant interest in medicinal chemistry.

In the pharmaceutical industry, 1-methyl-4-piperidone has been studied for its potential use as a precursor in the synthesis of various therapeutic agents. Research has indicated that its derivatives may exhibit biological activity, particularly in the realm of central nervous system (CNS) disorders. Some studies have explored its role as a potential agent for treating conditions such as anxiety and depression, although further research is needed to fully understand its pharmacological effects.

Beyond its applications in organic synthesis and pharmaceuticals, 1-methyl-4-piperidone is also utilized in the production of specialty chemicals, such as solvents and plasticizers. Its favorable solvent properties allow it to be used in various formulations, enhancing the solubility and stability of active ingredients.

Safety considerations when handling 1-methyl-4-piperidone include standard laboratory practices. It is advisable to avoid direct contact with skin and eyes, as well as to work in a well-ventilated area, due to its potential irritant properties.

In conclusion, 1-methyl-4-piperidone is a significant compound in the fields of organic synthesis and pharmaceuticals. Its unique structure and versatile applications continue to drive research and development efforts, particularly in the search for new therapeutic agents and advanced chemical products.

References

2024-05-29. High-performance spiro-branched polymeric membranes for sustainability applications
DOI: 10.1038/s41893-024-01364-0

2023-03-23. Pt single atoms coupled with Ru nanoclusters enable robust hydrogen oxidation for high-performance anion exchange membrane fuel cells
DOI: 10.1007/s12274-024-6604-7

2017-09-05. 3,5-Bis(2-fluorobenzylidene)-4-piperidone induce reactive oxygen species-mediated apoptosis in A549 cells
DOI: 10.1007/s00044-017-2056-x