N-Cyclohexyl-2-pyrrolidone
[CAS# 6837-24-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: N-Cyclohexyl-2-pyrrolidone
• Synonyms: CHP
• Molecular Formula: C₁₀H₁₇NO
• Molecular Weight: 167.25
• CAS Registry Number: 6837-24-7
• EC Number: 229-919-7
• SMILES: C1CCC(CC1)N2CCCC2=O

Properties

• Density: 1.007
• Melting point: 12 °C
• Boiling point: 154 °C (7 mmHg)
• Refractive index: 1.4975-1.4995
• Flash point: 145 °C
• Water solubility: Soluble

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302+H312-H302-H312-H314-H318
• Safety Statements: P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 2810

Discovery and Applications

N-Cyclohexyl-2-pyrrolidone is a nitrogen-containing heterocyclic compound belonging to the family of pyrrolidones, characterized by a five-membered ring structure that includes a nitrogen atom. This compound has drawn significant interest in various fields, particularly in organic synthesis, pharmaceuticals, and materials science, due to its unique properties and versatile applications.

The discovery of N-cyclohexyl-2-pyrrolidone can be traced back to the ongoing research into pyrrolidone derivatives in the mid-20th century. These compounds were initially investigated for their potential as solvents and intermediates in chemical reactions. The introduction of a cyclohexyl group enhances the solubility and compatibility of the compound with various organic materials, making it a valuable addition to the field of organic chemistry.

One of the primary applications of N-cyclohexyl-2-pyrrolidone is as a solvent in chemical processes. Its polar aprotic nature allows it to dissolve a wide range of organic compounds, making it particularly useful in organic synthesis and extraction processes. This property is beneficial in reactions involving nucleophilic substitutions, as the compound can stabilize reactive intermediates and facilitate the solubility of substrates. The use of N-cyclohexyl-2-pyrrolidone as a solvent has been shown to enhance reaction yields and improve product purity, making it a preferred choice in laboratory and industrial settings.

In the pharmaceutical industry, N-cyclohexyl-2-pyrrolidone serves as an important intermediate in the synthesis of various bioactive compounds. Its structure enables it to participate in a range of chemical transformations, allowing chemists to create complex molecules required for therapeutic agents. The compound has been utilized in the development of pharmaceuticals targeting various conditions, including infections and inflammatory diseases. Its compatibility with biological systems also makes it a candidate for drug delivery applications, where it can enhance the solubility and bioavailability of poorly soluble drugs.

Another significant application of N-cyclohexyl-2-pyrrolidone is in the field of polymer chemistry. It is used as a plasticizer and processing aid in the production of various polymer materials. Its ability to improve the flexibility and workability of polymers has made it valuable in the manufacturing of plastics, coatings, and adhesives. By incorporating N-cyclohexyl-2-pyrrolidone into polymer formulations, manufacturers can achieve improved mechanical properties and durability, enhancing the overall performance of the final products.

In addition to its industrial applications, N-cyclohexyl-2-pyrrolidone is being explored for its potential in biotechnological applications. Research has indicated that derivatives of this compound can exhibit biological activity, including antimicrobial and anti-inflammatory effects. This aspect has generated interest in the compound as a scaffold for drug discovery, particularly in the search for new therapeutic agents that can address unmet medical needs.

Despite its numerous applications, handling N-cyclohexyl-2-pyrrolidone requires caution. While it is generally considered safe when used appropriately, exposure to high concentrations may lead to health risks. Therefore, safety measures, including proper ventilation and personal protective equipment, are essential when working with this chemical. Regulatory agencies have established guidelines to ensure safe use and handling in various applications.

Recent research continues to explore the potential of N-cyclohexyl-2-pyrrolidone in new areas. Efforts are being made to develop more sustainable synthesis methods and to investigate its synergistic effects when combined with other solvents and additives. This ongoing research aims to expand the applications of N-cyclohexyl-2-pyrrolidone while minimizing environmental impacts.

In summary, N-cyclohexyl-2-pyrrolidone is a versatile compound with significant implications in organic synthesis, pharmaceuticals, and materials science. Its role as a solvent, intermediate, and processing aid underscores its importance in various chemical processes and product formulations. Ongoing exploration of its properties and applications promises to enhance its relevance in modern chemistry and related fields.

References

2005. Relevance of Frank's solvent classification as typically aqueous and typically non-aqueous to activities of firefly luciferase, alcohol dehydrogenase, and alpha-chymotrypsin in aqueous binaries. Archives of Biochemistry and Biophysics.
DOI: 10.1016/j.abb.2004.10.005

2002. Solvent effects on infrared spectra of 2-Methyl-4,5-dimethoxy-3-oxo-2H-pyridizine: Part 2. Binary solvent systems. Journal of Zhejiang University-SCIENCE A.
DOI: 10.1631/jzus.2002.0559