5-Vinyl-2-pyrrolidinone

Base Information

• Chemical Name: 5-Vinyl-2-pyrrolidinone
• CAS No.: 7529-16-0
• Molecular Formula: C6H9NO
• Molecular Weight: 111.144
• Hs Code.: 2922498050
• European Community (EC) Number: 616-206-4
• UNII: 739J1G8PUA
• DSSTox Substance ID: DTXSID001318830
• Nikkaji Number: J549.679I
• Wikidata: Q27266164
• Mol file: 7529-16-0.mol

Synonyms:7529-16-0;5-Vinylpyrrolidin-2-one;5-VINYLPYRROLIDONE;5-vinyl-2-pyrrolidinone;5-Ethenyl-2-pyrrolidinone;5-ethenylpyrrolidin-2-one;2-Pyrrolidinone, 5-ethenyl-;5-vinyl-pyrrolidin-2-one;2-Pyrrolidinone, 5-vinyl-;MDL 17637-03;5-vinyl-2-pyrrolidone;(+/-)-5-Vinylpyrrolidin-2-one;UNII-739J1G8PUA;739J1G8PUA;(5RS)-5-Ethenylpyrrolidin-2-one;EC 616-206-4;Vigabatrin impurity A;5-Ethenyl-2-pyrrolidinon;SCHEMBL14928;4-Amino-5-hexenoic acid lactam;DTXSID001318830;BCP26092;MFCD12911927;AKOS006347676;AS-49794;VIGABATRIN IMPURITY A [EP IMPURITY];CS-0315611;FT-0668057;N10616;Vigabatrin EP Impurity A;Q27266164

Chemical Property of 5-Vinyl-2-pyrrolidinone

Chemical Property:

• Vapor Pressure: 0.0234mmHg at 25°C
• Melting Point: 134.7 °C
• Refractive Index: 1.553
• Boiling Point: 249.1 °C at 760 mmHg
• PKA: 15.94±0.40(Predicted)
• Flash Point: 134.7°C
• PSA: 29.10000
• Density: 1.088 g/cm³
• LogP: 0.77980
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Sparingly), DMSO, Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 111.068413911
• Heavy Atom Count: 8
• Complexity: 120

Purity/Quality:

99.9% ^*data from raw suppliers

5-Ethenyl-2-pyrrolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1CCC(=O)N1
• Uses: Vigabatrin (V253000) impurity. Vigabatrin (V253000) impurity. Vigabatrin USP Related Compound A.

Technology Process of 5-Vinyl-2-pyrrolidinone

There total 17 articles about 5-Vinyl-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: 95.0%

4-amino-5-hexenoic acid (60643-86-9,68506-86-5) → 5(S)-Vinyl-2-Pyrrolidinone (7529-16-0)

Guidance literature:

at 180 ℃;

DOI:10.1021/ja9527885

Reference yield: 85.0%

1-(3,5-di-tert-butyl-2-hydroxyphenyl)-5-vinylpyrrolidin-2-one → 5(S)-Vinyl-2-Pyrrolidinone (7529-16-0)

Guidance literature:

With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃;

DOI:10.1021/acs.joc.6b02562

Reference yield: 83.0%

2-Oxo-5-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester → 5(S)-Vinyl-2-Pyrrolidinone (7529-16-0)

Guidance literature:

With magnesium methanolate; In methanol; at 25 ℃;

DOI:10.1016/S0040-4039(00)75979-X

upstream raw materials:

4-amino-5-hexenoic acid

5-vinyl-dihydrofuran-2(3H)-one

5-ethoxy-pyrrolidin-2-one

vinyl magnesium bromide

Downstream raw materials:

(+)-Vigabatrin

(R)-vigabatrin

(5S)-N-((2R)-2-(2,4-di-t-butylphenyloxy)propanoyl)-5-ethenylpyrrolidin-2-one

(5S)-N-((2R)-2-(3,5-di-t-butyl-4-hydroxyphenyl)thiopropanoyl)-5-ethenylpyrrolidin-2-one

Refernces

• 1、 Karumanchi, Kishore,Natarajan, Senthil Kumar,Gadde, Sunil,Vanchanagiri, Krishna. "A convenient approach for vinylation reaction in the synthesis of 5-vinyl-2-pyrrolidinone, a key intermediate of vigabatrin". . p. 2035 - 2039. Retrieved 2020/01/02.
• 2、 Xing, Qi,Chan, Chun-Ming,Yeung, Yiu-Wai,Yu, Wing-Yiu. "Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones". supporting information. . Retrieved 2019/03/11.