2-Methyl-N-phenylmaleimide

Base Information

• Chemical Name: 2-Methyl-N-phenylmaleimide
• CAS No.: 3120-04-5
• Molecular Formula: C11H9 N O2
• Molecular Weight: 187.198
• Hs Code.: 2925190090
• European Community (EC) Number: 626-011-6
• DSSTox Substance ID: DTXSID50351059
• Nikkaji Number: J257.927H
• Wikidata: Q82127159
• Metabolomics Workbench ID: 142989
• ChEMBL ID: CHEMBL567621
• Mol file: 3120-04-5.mol

Synonyms:2-Methyl-N-phenylmaleimide;3120-04-5;3-methyl-1-phenyl-1H-pyrrole-2,5-dione;3-methyl-1-phenylpyrrole-2,5-dione;1h-pyrrole-2,5-dione, 3-methyl-1-phenyl-;n-phenyl-2-methylmaleimide;3-Methylphenylmaleimide;starbld0001226;SCHEMBL774452;CHEMBL567621;DTXSID50351059;QAVUFFJVZGZJMO-UHFFFAOYSA-N;2-Methyl-N-phenylmaleimide, 98%;STK746810;3-Methyl-1-phenyl-pyrrole2,5-dione;AKOS001705881;3-Methyl-1-phenyl-pyrrole-2,5-dione;PD135229;EU-0050672;J-018278;3-METHYL-1-PHENYL-2,5-DIHYDRO-1H-PYRROLE-2,5-DIONE

Chemical Property of 2-Methyl-N-phenylmaleimide

Chemical Property:

• Vapor Pressure: 0.000718mmHg at 25°C
• Melting Point: 98-100 °C(lit.)
• Refractive Index: n20/D 1.568(lit.)
• Boiling Point: 262-264 °C(lit.)
• PKA: -0.76±0.40(Predicted)
• Flash Point: >230 °F
• PSA: 37.38000
• Density: 1.05 g/mL at 25 °C(lit.)
• LogP: 1.57110
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 187.063328530
• Heavy Atom Count: 14
• Complexity: 300

Purity/Quality:

98%Min ^*data from raw suppliers

2-METHYL-N-PHENYL MALEIMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=O)N(C1=O)C2=CC=CC=C2
• Uses: 2-Methyl-N-phenylmaleimide is a useful intermediate for the synthesis of maleimides with antifungal activities.

Technology Process of 2-Methyl-N-phenylmaleimide

There total 43 articles about 2-Methyl-N-phenylmaleimide 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-phenylitaconimide (34105-39-0) → 3-methyl-1-phenylpyrrole-2,5-dione (3120-04-5)

Guidance literature:

With triethylamine; In chloroform; Ambient temperature;

DOI:10.1246/cl.1984.281

Reference yield: 91.0%

citraconic acid anhydride (616-02-4) + aniline (62-53-3) → 3-methyl-1-phenylpyrrole-2,5-dione (3120-04-5)

Guidance literature:

With acetic acid; Reflux;

DOI:10.1002/adsc.201801436

Reference yield: 52.0%

1-(2-methyl-1-oxo-2-propenyl)pyrrolidine (35595-88-1) + phenyl isocyanate (103-71-9) → 3-methyl-1-phenylpyrrole-2,5-dione (3120-04-5)

Guidance literature:

With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In 1,2-dichloro-ethane; at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201404261

upstream raw materials:

citraconic acid anhydride

aniline

(+/-)-5-phenyl-(3ar,6ac)-3a,6a-dihydro-3H-pyrrolo[3,4-c]pyrazole-4,6-dione

7-Phenyl-2,3,7-triazabicyclo<3.3.0>oct-2-ene-6,8-dione

Downstream raw materials:

2-methyl-N-phenyl-maleamic acid

Refernces

• 1、 -. "Application of maleimide compound as chitin synthase inhibitor". Paragraph 0024-0027; 0040-0043. . Retrieved 2020/07/12.
• 2、 Yuan, Yu-Chao,Bruneau, Christian,Dorcet, Vincent,Roisnel, Thierry,Gramage-Doria, Rafael. "Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides". . p. 1898 - 1907. Retrieved 2019/02/05.