5-Methyl-2-pyrrolidone

Base Information

• Chemical Name: 5-Methyl-2-pyrrolidone
• CAS No.: 108-27-0
• Molecular Formula: C5H9NO
• Molecular Weight: 99.1326
• Hs Code.: 2933790090
• European Community (EC) Number: 203-566-9
• NSC Number: 75833
• UNII: 1X0OUE3QOB
• DSSTox Substance ID: DTXSID50870457
• Nikkaji Number: J5.071G
• Mol file: 108-27-0.mol

Synonyms:5-methylpyrrolidin-2-one;5-Methyl-2-pyrrolidone;108-27-0;5-Methyl-2-pyrrolidinone;2-Pyrrolidinone, 5-methyl-;gamma-Valerolactam;.gamma.-Valerolactam;1X0OUE3QOB;2-Pyrrolidinone,5-methyl-;EINECS 203-566-9;MFCD00005273;NSC 75833;NSC-75833;NSC75833;5-methylpyrrolidinone;5-methyl-2-pyrrolidinon;UNII-1X0OUE3QOB;5-methyl 2-pyrrolidinone;5-methyl-2-oxopyrrolidine;rac 5-Methyl-pyrrolidin-2-one;DTXSID50870457;5-Methyl-2-pyrrolidinone, 98%;CHEBI:183240;AKOS006220513;AS-58211;CS-0046659;M0406;EN300-82151;D72848;A854118;J-002082;F0001-0162;Z1250132456;95006AAB-BE49-4C57-A4EA-2D1A779707E9

Chemical Property of 5-Methyl-2-pyrrolidone

Chemical Property:

• Vapor Pressure: 0.0377mmHg at 25°C
• Melting Point: 41-43 °C
• Refractive Index: 1.439
• Boiling Point: 240.5 °C at 760 mmHg
• PKA: 16.68±0.40(Predicted)
• Flash Point: 127.5 °C
• PSA: 29.10000
• Density: 0.979 g/cm³
• LogP: 0.61370
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 99.068413911
• Heavy Atom Count: 7
• Complexity: 90.1

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Methyl-2-pyrrolidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(=O)N1

Technology Process of 5-Methyl-2-pyrrolidone

There total 53 articles about 5-Methyl-2-pyrrolidone 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: 99.0%

levulinic acid (123-76-2) → 5-methylpyrrolidin-2-one (108-27-0)

Guidance literature:

levulinic acid; With C₂₄H₂₂N₄*BF₄^(1-)*Ru⁽²⁺⁾*Cl^(1-)*C₁₀H₁₄; ammonium formate; In neat (no solvent); at 80 ℃; for 4h; Green chemistry;

at 120 ℃; for 20h; Reagent/catalyst; Temperature; Catalytic behavior; Green chemistry;

DOI:10.1039/c6gc02591a

Reference yield: 94.0%

levulinic acid ammonium salt + methylamine (74-89-5) → 1,5-dimethylpyrrolidin-2-one (5075-92-3) + 5-methylpyrrolidin-2-one (108-27-0)

Guidance literature:

With hydrogen; 0.7% Pd/C; In water; at 150 ℃; under 25877.6 Torr;

Reference yield: 93.0%

4-aminopentanoic acid (13880-74-5,349548-27-2) → 5-methylpyrrolidin-2-one (108-27-0)

Guidance literature:

With aluminum oxide; In toluene; for 5.5h; Heating;

DOI:10.1016/S0040-4039(00)93171-X

upstream raw materials:

5-methyl-5H-furan-2-one

4-aminopentanoic acid

4-(hydroxyimino)valeric acid

4-hydroxyimino-valeric acid ethyl ester

Downstream raw materials:

2-methyl-1-pyrrolidine

benzyl 2-methyl-5-oxopyrrolidine-1-carboxylate

(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((R)-2-methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-2-methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

Refernces

• 1、 Du, Xian-Long,He, Lin,Zhao, She,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian. "Hydrogen-independent reductive transformation of carbohydrate biomass into γ-valerolactone and pyrrolidone derivatives with supported gold catalysts". . p. 7815 - 7819. Retrieved 2011.
• 2、 Marson, Charles M.,Fallah, Asad. "Preparation of γ- and δ-lactams by ring closure of β,γ-unsaturated amides using trifluoromethanesulfonic acid". . p. 293 - 296. Retrieved 1994.
• 3、 Hall. "-". . p. 6404,6408. Retrieved 1958.
• 4、 Kweon, Jeonguk,Chang, Sukbok. "Highly Robust Iron Catalyst System for Intramolecular C(sp3)?H Amidation Leading to γ-Lactams". supporting information. p. 2909 - 2914. Retrieved 2020/12/11.
• 5、 Haus, Moritz O.,Hofmann, Jan P.,Konrad, Marc,Louven, Yannik,Palkovits, Regina. "Efficient palladium catalysis for the upgrading of itaconic and levulinic acid to 2-pyrrolidones followed by their vinylation into value-added monomers". . p. 4532 - 4540. Retrieved 2020/11/02.