123457-83-0

Usage

Uses

Used in Polymer Chemistry:
4-(Maleinimido)Phenyl Isocyanate is used as a reactive compound for the synthesis of polyurethane plastics. Its ability to form urethanes and urea with alcohol or amine groups makes it a key ingredient in the production of these versatile materials.
Used in the Creation of Complex Polymer Architectures:
In the field of polymer chemistry, 4-(Maleinimido)Phenyl Isocyanate is used as a component in click reactions, which allow for the efficient and selective formation of complex polymer structures. The maleinimido group's reactivity plays a crucial role in this process, enabling the construction of advanced materials with tailored properties.
Used in the Synthesis of Advanced Materials:
4-(Maleinimido)Phenyl Isocyanate is employed as a building block in the synthesis of advanced materials with specific properties. Its reactivity with various functional groups and participation in click reactions make it a valuable asset in the development of novel materials for diverse applications.

InChI:InChI=1/C11H6N2O3/c14-7-12-8-1-3-9(4-2-8)13-10(15)5-6-11(13)16/h1-6H

Upstream product

• 58174-51-9 N-[4-(azidocarbonyl)phenyl]maleimide 
• 17057-04-4 N-(4-carboxyphenyl)maleimide 
• 494209-30-2 C₁₅H₁₁NO₅ 
• 150-13-0 4-amino-benzoic acid 
• 29305-46-2 4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride 
• 5432-04-2 N-(4-carboxyphenyl)maleamic acid 

Downstream Products

• 756902-09-7 N-[p-(2-furfuryl-carbamate)phenylene]maleimide 
• 741270-61-1 C₄₀H₃₂N₄O₈ 
• 917918-44-6 rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid [4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl)-amide 

Relevant academic research and scientific papers

Bio-based thermosetting resins composed of aliphatic polyol-derived polymaleimides and allyleugenol

Bio-based bismaleimide (2MPD), trismaleimide (3MGC) and tetramaleimide (4MDG) were synthesized by reactions of 4-isocyanatophenylmaleimide with 1,3-propanediol, glycerol and α,α′-diglycerol, respectively. Although 2MPD did not melt until the temperature w

Maleimidophenyl isocyanates as postpolymerization modification agents and their applications in the synthesis of block copolymers

The maleimide structure is highly reactive, exemplified by thiol–ene click reactions with thiols and Diels–Alder reactions with furans. Although postpolymerization modifications and macromolecular conjugations involving maleimide units have been widely studied, mostly due to their selectivity and high reactivity, little has been reported on the one-pot postpolymerization introduction of maleimides in polymer chains. Herein, we report p-maleimidophenyl isocyanate and its derivatives as modification agents to introduce maleimide moieties by reaction with hydroxy groups into polymer chains. The high reactivity of the resulting modification agents and of the corresponding maleimide structures once inserted in the polymer chains was examined by studying their reaction kinetics. Furthermore, these modification agents were successfully applied to the synthesis of macromonomers for graft polymerization and various block copolymers, with, for example, AB-type, star-shaped, and H-shaped architectures.

Selectivity control by chemical modification of the recognition sites in two-point binding molecularly imprinted polymer

We demonstrated the possibility of modifying the selectivity of a two-point binding imprinted polymer by chemical modification of the binding sites inside the cavities. We used a thermally reversible bond for the preparation of the monomer-template complex, which allowed us to remove the template easily by means of a simple thermal reaction and to simultaneously introduce various functional groups into the cavity. A phenylmaleimide having an azidocarbonyl group was reacted with diethylstilbestrol (DES, template) to yield a monomer, where the template was linked to two polymerizable maleimido groups via a thermally reversible urethane bond. The polymerization of the monomer was carried out in the presence of ethylene glycol dimethacrylate (EGDMA) by the initiation with 2,2-azobis(isobutyronitrile) (AIBN) at 54°C in DMF. The polymers were refluxed in 1,4-dioxane in the presence of a nucleophile such as water, methanol, or aniline. In this extraction step, the template molecules were removed from the polymer matrix, and simultaneously the isocyanato groups, which were generated by the thermal cleavage of the urethane bond, were converted to amino, urethane, or urea groups through their reaction with water, methanol, or aniline, respectively. The specific recognition ability of the imprinted polymers for the template and its structural analogues was dependent on the space between the two binding points as well as on the nature of the functional group. This method is especially propitious for developing artificial receptors for molecules lacking strongly interactive groups.

Ab-monomers. I: Synthesis and polymerization of furyl-maleimide monomers

New AB-monomers containing either furyl and maleimide groups or hydroxy and acid groups were prepared by the reaction of 4-maleimidobenzoic acid chloride or 4-maleimidophenylisocyanate with 2-furfuryl alcohol or the Diels-Alder reaction of 4-maleimidobenzoic acid with 2-furfuryl alcohol, respectively. The structures of the monomers were confirmed by IR, 1H-NMR and elemental analysis. By Diels-Alder polymerization reaction or polycondensation reaction new poly(esther-imide) or poly(urethane-imide)s were prepared. Thermal curing behavior of monomers was investigated by DSC analysis. All polymers were characterized by elemental analysis, IR spectral studies and thermogravimetry.