N-ethylmaleimide

Base Information

• Chemical Name: N-ethylmaleimide
• CAS No.: 128-53-0
• Molecular Formula: C6H7NO2
• Molecular Weight: 125.127
• Hs Code.: 29251900
• European Community (EC) Number: 204-892-4
• NSC Number: 92547,7638
• UNII: O3C74ACM9V
• DSSTox Substance ID: DTXSID1059573
• Nikkaji Number: J21.254G
• Wikipedia: N-Ethylmaleimide
• Wikidata: Q292393
• Metabolomics Workbench ID: 49817
• ChEMBL ID: CHEMBL8211
• Mol file: 128-53-0.mol

Synonyms:Ethylmaleimide;N Ethylmaleimide;N-Ethylmaleimide

Chemical Property of N-ethylmaleimide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.197mmHg at 25°C
• Melting Point: 43-46 °C(lit.)
• Refractive Index: 1.514
• Boiling Point: 210 °C at 760 mmHg
• PKA: -2.18±0.20(Predicted)
• Flash Point: 73.3 °C
• PSA: 37.38000
• Density: 1.207 g/cm³
• LogP: -0.13080
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: methanol: 1 M at 20 °C, clear, colorless
• Water Solubility.: 1 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 125.047678466
• Heavy Atom Count: 9
• Complexity: 166

Purity/Quality:

98%, ^*data from raw suppliers

N-Ethylmaleimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 21-28-34-43-20/21
• Safety Statements: 26-28-36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CCN1C(=O)C=CC1=O
• Recent ClinicalTrials: NEM? Versus Placebo on Exercise-induced Joint Pain, Stiffness, & Cartilage Turnover In Healthy, Post-Menopausal Women
• Uses: Reagent for the covalent modification of cysteine residues in proteins. NEM gives a clear solution in ethanol at 50 mg/ml. NEM dissolves in water (>50 mg in 4 ml); however, aqueous solutions are unstable. The rate of hydrolysis is pseudo-first order and significantly dependent on pH. In cancer research (possible antimitotic activity.) N-Ethylmaleimide is a protein thiol modifier which inhibits apoptotic DNA fragmentation. It is a sulfhydryl reagent and finds application in experimental biochemical studies as well as in enzymology. It is involved in the modification of cysteine residues in proteins and peptides. It acts as a Michael acceptor and reacts with nucelophiles like thiols. It is employed in the inhibition of Mg2+ dependent internucleosomal DNA fragmentation.

Technology Process of N-ethylmaleimide

There total 13 articles about N-ethylmaleimide 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: 85.0%

maleic anhydride (108-31-6) + ethylamine (75-04-7,85404-22-4) → N-Ethylmaleimide (128-53-0)

Guidance literature:

With sulfuric acid; copper(II) sulfate; sodium sulfate; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 ℃; for 2h;

DOI:10.1002/ardp.201600047

Reference yield: 52.0%

3-Pyrroline (109-96-6,760178-50-5) + ethyl bromide (74-96-4) → N-Ethylmaleimide (128-53-0)

Guidance literature:

With DBN; oxygen; rose bengal; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Irradiation;

DOI:10.1021/acscatal.8b01897

Reference yield:

C11H15NO3 → 2-methylfuran (534-22-5) + N-Ethylmaleimide (128-53-0)

Guidance literature:

In [D₃]acetonitrile; at 60 ℃; Kinetics;

DOI:10.1002/anie.200805303

upstream raw materials:

N-ethyl maleamic acid

2-ethyl-4-methyl-hexahydro-4,7-epioxido-isoindole-1,3-dione

maleic anhydride

ethanamine hydrochloride

Downstream raw materials:

3-(4-chloro-phenyl)-1-ethyl-pyrrole-2,5-dione

2-(1-ethyl-2,5-dioxo-pyrrolidin-3-ylmercapto)-benzoic acid

2-ethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione

3-(4-chloro-phenyl)-5-ethyl-(3ar,6ac)-3a,6a-dihydro-pyrrolo[3,4-d]isothiazole-4,6-dione

Refernces

• 1、 Rakibuddin, Md.,Gazi, Sarifuddin,Ananthakrishnan, Rajakumar. "Iron(II) phenanthroline-resin hybrid as a visible light-driven heterogeneous catalyst for green oxidative degradation of organic dye". . p. 53 - 58. Retrieved 2014.
• 2、 Kumar, Rakesh,Chaudhary, Sandeep,Kumar, Rohit,Upadhyay, Pooja,Sahal, Dinkar,Sharma, Upendra. "Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N′-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite". . p. 11552 - 11570. Retrieved 2018/09/25.
• 3、 Zhang, Yu,Riemer, Daniel,Schilling, Waldemar,Kollmann, Jiri,Das, Shoubhik. "Visible-Light-Mediated Efficient Metal-Free Catalyst for α-Oxygenation of Tertiary Amines to Amides". . p. 6659 - 6664. Retrieved 2018/06/25.