63853-74-7

Basic information

• Product Name: 5-METHOXY-2-PYRROLIDINONE
• Synonyms: 5-METHOXY-2-PYRROLIDINONE;5-Methoxy-2-oxopyrrolidine
• CAS NO: 63853-74-7
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• Product Categories: Various Intermediates;Intermediates;Heterocycles
• Mol File: 63853-74-7.mol
• Article Data: 21

Chemical Properties

• Melting Point: 52-55°C
• Boiling Point: 87-90°C@0.14Hg
• Flash Point: 116.2°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0.00767mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Soluble), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 5-METHOXY-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-2-PYRROLIDINONE(63853-74-7)
• EPA Substance Registry System: 5-METHOXY-2-PYRROLIDINONE(63853-74-7)

Safety Data

• Hazardous Substances Data: 63853-74-7(Hazardous Substances Data)

Usage

Description

5-METHOXY-2-PYRROLIDINONE is a synthetic intermediate with a molecular formula of C5H9NO2 and a molecular weight of 113.13 g/mol. It is a colorless to pale yellow liquid with a mild odor and is soluble in water and various organic solvents. 5-METHOXY-2-PYRROLIDINONE is known for its reactivity and versatility in organic synthesis, making it a valuable building block in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
5-METHOXY-2-PYRROLIDINONE is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows it to be easily modified and incorporated into complex molecules, making it a valuable tool for the development of new drugs.
Used in the Synthesis of γ-Lactam Antibiotics:
5-METHOXY-2-PYRROLIDINONE is used as a key intermediate in the synthesis of γ-lactam analogs of penems and carbapenems. These antibiotics are known for their broad-spectrum activity against a wide range of bacteria, including antibiotic-resistant strains. The incorporation of 5-METHOXY-2-PYRROLIDINONE into these compounds enhances their stability and effectiveness, leading to improved treatment outcomes for patients.
Used in Organic Synthesis:
5-METHOXY-2-PYRROLIDINONE is used as a versatile intermediate in organic synthesis for the preparation of various organic compounds. Its reactivity allows it to participate in a range of chemical reactions, such as nucleophilic addition, substitution, and rearrangement reactions. This makes it a valuable building block for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in the Production of Fine Chemicals:
5-METHOXY-2-PYRROLIDINONE is used as an intermediate in the production of fine chemicals, which are high-purity chemicals used in various applications, such as research, diagnostics, and the synthesis of other specialty chemicals. Its unique properties and reactivity make it an essential component in the synthesis of these high-value products.

InChI:InChI=1/C5H9NO2/c1-8-5-3-2-4(7)6-5/h5H,2-3H2,1H3,(H,6,7)

Upstream product

• 67-56-1 methanol 
• 33744-04-6 1-chloropyrrolidin-2-one 
• 62312-55-4 rac-4-hydroxy-2-pyrrolidone 
• 39662-63-0 5-ethoxy-pyrrolidin-2-one 
• 124-41-4 sodium methylate 
• 149-87-1 Pyroglutamic acid 
• 123-56-8 Succinimide 
• 616-45-5 2-pyrrolidinon 

Downstream Products

• 128628-08-0 3-Oxo-2-(5-oxo-pyrrolidin-2-yl)-3-phenyl-propionic acid ethyl ester 
• 111711-82-1 1-Benzenesulfonyl-5-methoxy-pyrrolidin-2-one 
• 7529-16-0 5(S)-Vinyl-2-Pyrrolidinone 
• 76284-14-5 5-(phenylamino)pyrrolidin-2-one 
• 76284-15-6 5-(benzylamino)pyrrolidin-2-one 
• 91703-06-9 5-(4-phenylpiperazin-1-yl)pyrrolidin-2-one 

Relevant articles and documents

Cesium salts as superior catalysts for solvent-free modifications of biosourced pterolactam

γ-Lactam derivatives are widespread biologically active compounds, covering a large range of activities. Following our interest in both medicinal and green chemistries, we developed an original, cesium salts-mediated, scalable and solvent-free methodology to transform biosourced pyroglutamic acid and its derivatives to their N,N′-aminals, N,O,N,S-acetals and C5-substituted γ-lactams in good to excellent yields. This protocol is applicable to a large range of substrates, conducting to C5-substituted γ-lactam derivatives as potential new biologically active compounds.

Intramolecular [4+2] cycloaddition in n-allyl- and n-propargyl-α-furyl lactams

The size of nitrogen heterocycle in N-allyl- and N-propargyl-α-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-γ-(α-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230°С. Substituted δ-valero- and ε-caprolactams underwent partial Diels–Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-α-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp2-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.