N-Methylsuccinimide

Base Information

• Chemical Name: N-Methylsuccinimide
• CAS No.: 1121-07-9
• Molecular Formula: C5H7NO2
• Molecular Weight: 113.116
• Hs Code.: 2925190090
• European Community (EC) Number: 628-414-2
• NSC Number: 11324
• UNII: FT9GT286W2
• DSSTox Substance ID: DTXSID40149902
• Nikkaji Number: J45.655A
• Wikidata: Q27462406
• ChEMBL ID: CHEMBL317929
• Mol file: 1121-07-9.mol

Synonyms:N-methylsuccinimide

Chemical Property of N-Methylsuccinimide

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 0.0542mmHg at 25°C
• Melting Point: 61-70 °C(lit.)
• Refractive Index: 1.493
• Boiling Point: 234 °C at 760 mmHg
• PKA: -1.34±0.20(Predicted)
• Flash Point: 105.9 °C
• PSA: 37.38000
• Density: 1.219 g/cm³
• LogP: -0.29690
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 113.047678466
• Heavy Atom Count: 8
• Complexity: 125

Purity/Quality:

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

N-Methylsuccinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-41
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Succinimides
• Canonical SMILES: CN1C(=O)CCC1=O
• Uses: N-Methylsuccinimide is used as a model compound to investigate the mechanism of enolization step by density-functional theory (DFT) calculations. N-Methylsuccinimide is a metabolite of N-methyl-2-pyrrolidone (NMP) and its presence in plasma and urine can be used as a biomarker of exposure to NMP

Technology Process of N-Methylsuccinimide

There total 60 articles about N-Methylsuccinimide 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: 100.0%

N-methylmaleimide (930-88-1) → N-methylsuccinimide (1121-07-9)

Guidance literature:

With acetic anhydride; zinc; In toluene; at 40 - 86 ℃; for 48h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/jhet.2469

Reference yield: 91.0%

1-methyl-pyrrolidin-2-one (872-50-4,26138-58-9) → N-methylsuccinimide (1121-07-9)

Guidance literature:

With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetramesitylporphyrinato)ruthenium(IV); In benzene; at 40 ℃;

DOI:10.1021/ja045603f

Reference yield: 81.0%

N-(benzylthio)succinimide (14204-23-0) + phosphorous acid trimethyl ester (121-45-9) → N-methylsuccinimide (1121-07-9) + O,O-dimethyl S-(benzyl) phosphorothioate (7205-16-5)

Guidance literature:

In toluene; Ambient temperature;

DOI:10.1016/0040-4039(90)87018-U

upstream raw materials:

diazomethane

Succinimide

methanol

1-phenyl-3-methyltriazene

Downstream raw materials:

5-(4-bromo-phenyl)-5-hydroxy-1-methyl-pyrrolidin-2-one

5-Hydroxy-1-methyl-5-phenylpyrrolidin-2-one

1-methyl-2,5-diphenyl-pyrrole

phenacylacetophenone

Refernces

• 1、 Talukdar, Dhrubajyoti,Saikia, Lakhinath,Thakur, Ashim Jyoti. "Zirconyl chloride: An efficient, water-tolerant, and reusable catalyst for the synthesis of N-methylamides". . p. 1597 - 1601. Retrieved 2011.
• 2、 Kleber, Carlos,Andrade,Matos, Ricardo Alexandre F.. "Niobium pentachloride-mediated nucleophilic additions to cyclic N-acyliminium ions". . p. 1189 - 1191. Retrieved 2003.
• 3、 Barry, John E.,Finkelstein, Manuel,Moore, W. Michael,Ross, Sidney D.. "Rates and Mechanism in the Electron Transfer Mediated Reduction of N-Chlorosuccinimide by Succcinimide Anion.". . p. 528 - 531. Retrieved 1985.
• 4、 Lei, Aiwen,Wan, Zhaohua,Wang, Dan,Wang, Shengchun,Yang, Zixuan,Zhang, Heng. "Electrochemical oxidative C(sp3)-H azolation of lactams under mild conditions". . p. 3742 - 3747. Retrieved 2020.
• 5、 Tsuchimoto, Teruhisa,Ozawa, Yoshitaka,Negoro, Ryoju,Shirakawa, Eiji,Kawakami, Yusuke. "Zirconium triflate catalyzed direct coupling reaction of lactams with heterocyclic arenes under atmospheric oxygen". . p. 4231 - 4233. Retrieved 2004.
• 6、 Gramain et al.. "-". . p. 194. Retrieved 1976.
• 7、 Needles,Whitfield. "-". . p. 341. Retrieved 1966.
• 8、 Longwitz, Lars,Werner, Thomas. "Reduction of Activated Alkenes by PIII/PV Redox Cycling Catalysis". supporting information. p. 2760 - 2763. Retrieved 2020/02/05.