541-59-3 Usage
Description
Maleimide, also known as 2,5-Pyrroledione, is a cyclic dicarboximide characterized by its 1H-pyrrole-2,5-dione structure. It is a slight yellow crystalline powder that serves as a nanoparticle surface functional group, which favors easy conjugation with cell penetration peptides through click chemistry, thus preserving its biofunctions.
Uses
Used in Chemical Synthesis:
Maleimide is used as a chemical intermediate for Rhodium-catalyzed conjugate arylation with arylboronic acids, enabling the formation of new chemical bonds and expanding the scope of synthetic applications.
Used in Bioconjugation:
Maleimide is used as a bioconjugation agent for immobilizing the bovine serum albumin-boronic acid conjugates in association with silica beads. Its nanoparticle surface favors the conjugation with cell penetration peptides, enhancing the bioavailability and therapeutic outcomes of the conjugated molecules.
Used in Polymer Chemistry:
Maleimide is used as a crosslinking reagent in polymer chemistry, allowing the formation of covalent bonds between polymer chains, which can improve the mechanical properties and stability of the resulting materials.
Used in Michael Additions and Diels-Alder Reactions:
Maleimide is used as a reactant in Michael additions and Diels-Alder reactions, where it participates in the addition across the double bond, leading to the formation of new chemical structures with potential applications in various industries.
Used in Biochemical Applications:
Maleimide is used as a reactant that quantitatively reacts with sulfhydryl groups, making it a valuable tool in the development of biochemical assays, protein modifications, and other applications involving the modification of thiol-containing molecules.
Hazard
A poison.
Safety Profile
Poison by
intraperitoneal and intravenous routes. An
experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits toxic fumes of NOx.
Purification Methods
Purify it by sublimation in a vacuum. The UV has max at 216 and 280nm in EtOH. [de Wolf & van de Straete Bull Soc Chim Belg 44 288 1935, UV: Rondestvedt et al. J Am Chem Soc 78 6115 1956, IR: Chiorboli & Mirone Ann Chim (Rome) 42 681 1952, Beilstein 21/10 V 3.]
Check Digit Verification of cas no
The CAS Registry Mumber 541-59-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 1 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 541-59:
(5*5)+(4*4)+(3*1)+(2*5)+(1*9)=63
63 % 10 = 3
So 541-59-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
541-59-3Relevant articles and documents
Preparation method of maleimide
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Paragraph 0061; 0066-0069; 0070; 0075-0078, (2022/03/27)
The invention provides a preparation method of maleimide, which comprises the following steps: S1, reacting maleic anhydride with p-methoxybenzylamine to generate 3-(4-methoxybenzylamino) acrylic acid; step S2, enabling the 3-(4-methoxybenzyl carbamoyl) acrylic acid to react with acetic anhydride, so as to generate 1-(4-methoxybenzyl) maleimide; and S3, removing the 1-(4-methoxybenzyl) group from the 1-(4-methoxybenzyl) maleimide under the action of an oxidizing agent, so as to generate the maleimide. The preparation method provided by the embodiment of the invention has the advantages of short experimental route, high raw material safety, strong experimental operability and suitability for industrial production.
Chemical-Switching Strategy for Synthesis and Controlled Release of Norcantharimides from a Biomass-Derived Chemical
Chang, Hochan,Huber, George W.,Dumesic, James A.
, p. 5213 - 5219 (2020/08/27)
Catalytic strategies were developed to synthesize and release chemicals for applications in fine chemicals, such as drugs and polymers, from a biomass-derived chemical, 5-hydroxymethyl furfural (HMF). The combination of the diene and aldehyde functionalities in HMF enabled catalytic production of acetalized HMF derivatives with diol or epoxy reactants to allow reversible synthesis of norcantharimide derivatives upon Diels-Alder reaction with maleimides. Reverse-conversion of the acetal group to an aldehyde yielded mismatches of the molecular orbitals in norcantharimides to trigger retro Diels-Alder reaction at ambient temperatures and released reactants from the coupled molecules under acidic conditions. These strategies provide for the facile synthesis and controlled release of high-value chemicals.
Synthesis method of maleimide
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Paragraph 0016; 0022; 0023;, (2018/06/21)
The invention relates to the technical field of maleimide synthesis, in particular to a synthesis method of maleimide. According to the method, maleic anhydride serves as an initial raw material, andN-carbamoylmaleimide is obtained through an aminolysis reaction of urea and a dehydration reaction of acetic anhydride; in the presence of triethylamine, N-carbamoylmaleimide is heated and decomposedinto maleimide. The whole process is simple in operation, the product quality is high, and industrial production is easy.