7529-16-0

Basic information

• Product Name: 5-Vinylpyrrolidone
• Synonyms: 5-Vinylpyrrolidon-2;5-VINYLPYRROLIDONE;5-Ethenylpyrrolidin-2-one;5-Ethenyl-2-pyrrolidinone;(±)-5-Vinylpyrrolidin-2-one;5-Vinyl-2-pyrrolidinone;MDL 17637-03;Vigabatrin Related CoMpound A
• CAS NO: 7529-16-0
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• Product Categories: Heterocycles;Impurities
• Mol File: 7529-16-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 249.1 °C at 760 mmHg
• Flash Point: 134.7°C
• Appearance: /
• Density: 1.088 g/cm³
• Vapor Pressure: 0.0234mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform (Sparingly), DMSO, Methanol (Slightly)
• PKA: 15.94±0.40(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 5-Vinylpyrrolidone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Vinylpyrrolidone(7529-16-0)
• EPA Substance Registry System: 5-Vinylpyrrolidone(7529-16-0)

Safety Data

• Hazardous Substances Data: 7529-16-0(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

Uses

Different sources of media describe the Uses of 7529-16-0 differently. You can refer to the following data:
1. Vigabatrin (V253000) impurity.
2. Vigabatrin (V253000) impurity. Vigabatrin USP Related Compound A.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 847, 1994 DOI: 10.1016/S0040-4039(00)75979-X

InChI:InChI=1/C6H9NO/c1-2-5-3-4-6(8)7-5/h2,5H,1,3-4H2,(H,7,8)

Upstream product

• 60643-86-9 4-amino-5-hexenoic acid 
• 125348-98-3 2-vinylpyrrolidine hydrochloride 
• 1577-22-6 5-hexenoic acid 
• 39662-63-0 5-ethoxy-pyrrolidin-2-one 
• 925-90-6 ethylmagnesium bromide 
• 1826-67-1 vinyl magnesium bromide 
• 1159991-78-2 N-hydroxyhex-5-enamide 
• 2396-80-7 methyl 5-hexenoate 
• 123-56-8 Succinimide 
• 3536-96-7 vinylmagnesium chloride 
• 63853-74-7 5-methoxypyrrolidin-2-one 
• 21963-38-2 5-vinyl-dihydrofuran-2(3H)-one 

Downstream Products

• 60643-86-9 4-amino-5-hexenoic acid 
• 1160846-22-9 1-(p-tolylsulfonyl)-5-vinylpyrrolidin-2-one 
• 143418-07-9 (5S)-N-((2R)-2-(3,5-di-t-butyl-4-hydroxyphenyl)thiopropanoyl)-5-ethenylpyrrolidin-2-one 
• 143417-98-5 (5S)-N-((2R)-2-(2,4-di-t-butylphenyloxy)propanoyl)-5-ethenylpyrrolidin-2-one 
• 132114-52-4 (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-43-3 [2-(1-Acetoxy-allyl)-5-oxo-pyrrolidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester 
• 132114-42-2 [2-(1-Acetoxy-allyl)-5-oxo-pyrrolidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester 
• 132114-34-2 Sodium; (1S,7aR)-1-hydroxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate 
• 132114-50-2 (1R,7aR)-1-Acetoxy-2-ethylsulfanyl-5-oxo-hexahydro-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-53-5 (1R,7aR)-1-Acetoxy-2-ethylsulfanyl-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-51-3 (1R,7aR)-1-Acetoxy-2,5-dioxo-hexahydro-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-46-6 (1S,7aR)-1-Acetoxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-45-5 (1S,7aR)-1-Acetoxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester 
• 132114-47-7 (1S,7aR)-1-Formyloxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester 

Relevant articles and documents

Mechanisms of inactivation of gamma-aminobutyric acid aminotransferase by 4-amino-5-fluoro-5-hexenoic acid

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A convenient approach for vinylation reaction in the synthesis of 5-vinyl-2-pyrrolidinone, a key intermediate of vigabatrin

A convenient, safe and cost-effective method for carrying out the key vinylation of 5-ethoxy-2-pyrrolidinone (8) in the preparation of 5-vinyl-2-pyrrolidinone (2) in the presence of potassium carbonate is described. This present procedure is developed by replacing inherently hazardous ethyl magnesium bromide with inexpensive and eco-friendly potassium carbonate. The reaction was performed on a multi-gram scale, with vinyl magnesium bromide as the vinylation reagent, in an 81% yield to give the 5-vinyl-2-pyrrolidinone with excellent purity and without the need for chromatography.

Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C - H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C - H bonds was also achieved with remarkable tolerance to the C=C and C=C bonds.