2-Pyrrolidinone

Base Information

• Chemical Name: 2-Pyrrolidinone
• CAS No.: 616-45-5
• Molecular Formula: C4H7NO
• Molecular Weight: 85.1057
• Hs Code.: 29339980
• European Community (EC) Number: 210-483-1
• ICSC Number: 0562
• NSC Number: 8413,4593
• UNII: KKL5D39EOL
• DSSTox Substance ID: DTXSID8027246
• Nikkaji Number: J1.663B
• Wikipedia: 2-Pyrrolidone
• Wikidata: Q285640
• RXCUI: 1358473
• Pharos Ligand ID: 1Z4FCLDQPKFW
• Metabolomics Workbench ID: 37989
• ChEMBL ID: CHEMBL276849
• Mol file: 616-45-5.mol

Synonyms:2-pyrrolidinone;2-pyrrolidone;2-pyrrolidone, (18)O-labeled;2-pyrrolidone, 5-(14)C-labeled;2-pyrrolidone, aluminum salt;2-pyrrolidone, cerium salt;2-pyrrolidone, hydrobromide;2-pyrrolidone, hydrochloride;2-pyrrolidone, hydrotribromide;2-pyrrolidone, lithium salt;2-pyrrolidone, potassium salt;2-pyrrolidone, rubidium salt;2-pyrrolidone, sodium salt

Chemical Property of 2-Pyrrolidinone

Chemical Property:

• Appearance/Colour: clear colorless liquid or low melting solid
• Vapor Pressure: 0.04 hPa (20 °C)
• Melting Point: 23-25 °C(lit.)
• Refractive Index: 1.480-1.490
• Boiling Point: 245 °C at 760 mmHg
• PKA: 16.62±0.20(Predicted)
• Flash Point: 135.5 °C
• PSA: 29.10000
• Density: 1.047 g/cm³
• LogP: 0.22520
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: miscible (completely)
• Water Solubility.: miscible
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 85.052763847
• Heavy Atom Count: 6
• Complexity: 69.9

Purity/Quality:

2-[p- ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1CC(=O)NC1
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the skin, eyes and respiratory tract.
• Uses: 2-Pyrrolidinone is a widely used organic polar solvent for various applications. 2-Pyrrolidinone is also an intermediate in the manufacture of polymers. 2-pyrrolidone widely exists in various physiologically active natural products in nature. For example, it is the main structural unit of gonadotropin releasing hormone. At the same time, 2-pyrrolidone is an important raw material and intermediate of medicine, pesticide, dye, peptide and other chemicals. If it is used as the end chain of peptide, it also plays a stable role in the conformation of the compound. Many polysubstituted 2-pyrrolidones have been used in the synthesis and production of a variety of drugs and applied for patents.

Technology Process of 2-Pyrrolidinone

There total 193 articles about 2-Pyrrolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

1-benzoylpyrrolidin-2-one (2399-66-8) → 2-pyrrolidinon (616-45-5) + benzaldehyde (100-52-7)

Guidance literature:

With Schwartz's reagent; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.10.006

Reference yield: 60.0%

N-trimethylsilyl-pyrrolidin-2-one (14468-90-7) + 1-chloroethyl ethyl ether (7081-78-9) → 2-pyrrolidinon (616-45-5) + 1-ethenyl-2-pyrrolidinone (88-12-0)

Guidance literature:

mercury dibromide;

Reference yield: 24.0%

Acetic acid 2,2-dichloro-1-(2-oxo-pyrrolidin-1-yl)-ethyl ester (151455-45-7) → 2-pyrrolidinon (616-45-5) + 1-ethenyl-2-pyrrolidinone (88-12-0) + 1-[(Z)-2-chloroethenyl]-2-pyrrolidinone + 1-((E)-2-Chloro-vinyl)-pyrrolidin-2-one

Guidance literature:

With tetraethylammonium perchlorate; In acetonitrile; at 20 ℃; Yields of byproduct given; electroreduction: mercury pool cathode; working potential 2.4 V (versus SCE);

upstream raw materials:

4-butanolide

Succinimide

glutaric anhydride,

γ-chlorobutyric acid

Downstream raw materials:

1-(2-hydroxyethyl)-2-pyrrolidinone

4-(2,5-dioxopyrrolidin-1-yl)butanoic acid

N-(2-hydroxy-2-phenylethyl)pyrrodidin-2-one

1-methyl-pyrrolidin-2-one

Refernces

• 1、 Yang, Dan,Zhu, Yan. "Evolution of catalytic activity driven by structural fusion of icosahedral gold cluster cores". . p. 245 - 250. Retrieved 2021.
• 2、 Ratcliff et al.. "-". . p. 1481,1486. Retrieved 1974.
• 3、 Hatada et al.. "-". . p. 166,167. Retrieved 1975.
• 4、 Guedez, Thanee,Nunez, Andres,Tineo, Evis,Nunez, Oswaldo. "Ring size configuration effect and the transannular intrinsic rates in bislactam macrocycles". . p. 2078 - 2082. Retrieved 2002.
• 5、 Chatterjee, Puranjan,Kanbur, Uddhav,Manzano, J. Sebastián,Sadow, Aaron D.,Slowing, Igor I.,Wang, Hsin. "Surface ligands enhance the catalytic activity of supported Au nanoparticles for the aerobic α-oxidation of amines to amides". . p. 1922 - 1933. Retrieved 2022/04/07.
• 6、 Sarak, Sharad,Sung, Sihyong,Jeon, Hyunwoo,Patil, Mahesh D.,Khobragade, Taresh P.,Pagar, Amol D.,Dawson, Philip E.,Yun, Hyungdon. "An Integrated Cofactor/Co-Product Recycling Cascade for the Biosynthesis of Nylon Monomers from Cycloalkylamines". . p. 3481 - 3486. Retrieved 2020/12/17.