2-Pyrrolidinone
[CAS# 616-45-5]

Identification

• Classification: Analytical chemistry >> Standard >> Pharmacopoeia standards and magazine standards
• Name: 2-Pyrrolidinone
• Synonyms: 2-Pyrrolidone; Butyrolactam
• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.10
• CAS Registry Number: 616-45-5
• EC Number: 210-483-1
• SMILES: C1CC(=O)NC1

Properties

• Density: 1.103
• Melting point: 25.5 ºC
• Boiling point: 250 ºC
• Refractive index: 1.486-1.488
• Flash point: 138 ºC
• Water solubility: miscible

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Hazard Statements: H315-H318-H319-H335-H360-H360D
• Precautionary Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	1B	H360D
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H336
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H311
Reproductive toxicity	Repr.	2	H361
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2-Pyrrolidinone, also known as gamma-butyrolactam (GBL), is a cyclic amide with a five-membered ring structure that has garnered significant attention in various fields, including organic chemistry, pharmaceuticals, and materials science. The compound is characterized by its versatile chemical properties and the ability to act as a solvent, reagent, and intermediate in numerous chemical processes.

The discovery of 2-pyrrolidinone dates back to the early 20th century when researchers began investigating lactams as potential building blocks for various organic compounds. Its unique structure, which includes a nitrogen atom within the ring, offers distinct reactivity patterns, making it an attractive target for synthesis and application. The compound is synthesized through the lactamization of amino acids or through the chemical transformation of other organic compounds, allowing for its availability in both laboratory and industrial settings.

One of the primary applications of 2-pyrrolidinone is as a solvent in chemical processes. Its polar aprotic nature enables it to dissolve a wide range of organic compounds, making it valuable in the synthesis of pharmaceuticals and agrochemicals. 2-Pyrrolidinone is particularly useful in reactions involving nucleophilic substitutions, as it can stabilize charged intermediates and facilitate the solubility of reactants. This property enhances the efficiency of various reactions, leading to higher yields of desired products.

In the pharmaceutical industry, 2-pyrrolidinone serves as an important intermediate in the synthesis of numerous drugs. Its ability to participate in various chemical transformations allows chemists to create complex molecular frameworks required for bioactive compounds. For instance, 2-pyrrolidinone is used in the synthesis of pyrrolidine derivatives, which are prevalent in several therapeutic agents. The incorporation of this lactam into drug design has proven beneficial in enhancing pharmacological properties, such as solubility and bioavailability.

Another significant application of 2-pyrrolidinone is in the production of polymers and resins. It acts as a monomer in the synthesis of poly(2-pyrrolidinone), which exhibits favorable thermal and mechanical properties. These polymers find utility in coatings, adhesives, and sealants due to their stability and durability. The versatility of 2-pyrrolidinone in polymer chemistry highlights its importance in developing advanced materials that meet the demands of various industrial applications.

2-Pyrrolidinone is also explored for its potential in biotechnology. Its structure allows it to interact with biological systems, making it a candidate for drug delivery systems and bioactive formulations. Research has indicated that derivatives of 2-pyrrolidinone can exhibit biological activity, including antimicrobial and anti-inflammatory properties. This aspect has spurred interest in the compound as a scaffold for drug discovery and development, particularly in the search for new therapeutic agents.

Despite its numerous applications, handling 2-pyrrolidinone requires caution. The compound is considered a potential irritant, and exposure can lead to adverse health effects. Therefore, appropriate safety measures, including the use of personal protective equipment and adequate ventilation, are essential when working with this chemical. Regulatory agencies have established guidelines for the safe use of 2-pyrrolidinone, emphasizing the need for careful handling and disposal.

Recent studies are focused on optimizing the synthesis of 2-pyrrolidinone and exploring its applications in new fields. Researchers are investigating environmentally friendly synthesis routes and greener alternatives to traditional chemical processes, aligning with the growing emphasis on sustainability in the chemical industry. This ongoing research aims to enhance the efficiency and safety of 2-pyrrolidinone while expanding its utility in various applications.

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

References

1984. 2-Pyrrolidinone and succinimide endogenously present in several mammalian species. Life Sciences, 35(22).
DOI: 10.1016/0024-3205(84)90461-2

2010. Calcium and zinc complexes of pyrroglutamate analogs detected by electrospray ionization mass spectrometry. Amino Acids, 39(5).
DOI: 10.1007/s00726-010-0697-x

2000. Hydrolytic Stability versus Ring Size in Lactams: Implications for the Development of Lactam Antibiotics and Other Serine Protease Inhibitors. Journal of Medicinal Chemistry, 43(21).
DOI: 10.1021/jm000921k