Maleimide

Base Information

• Chemical Name: Maleimide
• CAS No.: 541-59-3
• Molecular Formula: C4H3NO2
• Molecular Weight: 97.0733
• Hs Code.: 29251995
• European Community (EC) Number: 208-787-4
• NSC Number: 13684
• UNII: 2519R1UGP8
• DSSTox Substance ID: DTXSID3049417
• Nikkaji Number: J6.395I
• Wikipedia: Maleimide
• Wikidata: Q6743002
• Metabolomics Workbench ID: 49849
• ChEMBL ID: CHEMBL387762
• Mol file: 541-59-3.mol

Synonyms:maleimide;maleimide, potassium, silver (+1) (2:1:1) salt;maleimide, silver (+1) salt

Chemical Property of Maleimide

Chemical Property:

• Appearance/Colour: slight yellow crystalline powder
• Melting Point: 91-93 °C(lit.)
• Refractive Index: 1.4543 (estimate)
• Boiling Point: 244.073 °C at 760 mmHg
• PKA: 8.52±0.20(Predicted)
• Flash Point: 136.574 °C
• PSA: 46.17000
• Density: 1.366 g/cm³
• LogP: -0.47220
• Storage Temp.: Refrigerator
• Solubility.: soluble in Methanol
• Water Solubility.: SOLUBLE
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 97.016378338
• Heavy Atom Count: 7
• Complexity: 132

Purity/Quality:

99% ^*data from raw suppliers

Maleimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,C
• Hazard Codes: T,C
• Statements: 25-34-43-36/37/38-36
• Safety Statements: 26-36/37/39-45-37/39-28A-7/9

MSDS Files:

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1=CC(=O)NC1=O
• Uses: Rhodium-catalyzed conjugate arylation with arylboronic acids.1 Reacts quantitatively with sulfhydryl groups.Maleimide is used to immobilize the bovine serum albumin-boronic acid conjugates in association with silica beads. Its nanoparticle surface favors the conjugation with cell penetration peptides. It is involved in Rhodium-catalyzed conjugate arylation with arylboronic acids. It is actively involved in Michael additions and Diels-Alder reactions by the addition across the double bond. It acts as crosslinking reagents in polymer chemistry.

Technology Process of Maleimide

There total 52 articles about Maleimide 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: 97.0%

maleic anhydride (108-31-6) + nickel diacetate (373-02-4,14998-37-9,33025-09-1,94044-50-5,98268-31-6) → maleiimide (541-59-3,25721-74-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide;

Reference yield: 93.0%

maleic anhydride (108-31-6) → maleiimide (541-59-3,25721-74-8)

Guidance literature:

With formamide; In neat (no solvent); for 0.5h; Reagent/catalyst; Milling; Heating; Green chemistry;

DOI:10.4067/S0717-97072017000200015

Reference yield: 60.0%

N-methoxycarbonylmaleimide (55750-48-6) → maleiimide (541-59-3,25721-74-8)

Guidance literature:

With sodium hydrogencarbonate;

upstream raw materials:

Succinimide

pyrrole

N-carbamoylmaleimide

2,5-dioxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butylamide

Downstream raw materials:

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

exo-7-oxabicyclo[2.2.1]hept-4-ene-2,3-dicarboximide

(3aR,4R,7S,7aS)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

3-(phenylamino)pyrrolidine-2,5-dione

Refernces

• 1、 -. "METHOD OF PRODUCING MALEIMIDE". Paragraph 0019. . Retrieved 2020/09/24.
• 2、 -. "Synthesis method of maleimide". Paragraph 0016; 0022; 0023;. . Retrieved 2018/06/21.