123457-83-0

Basic information

• Product Name: 4-(MALEINIMIDO)PHENYL ISOCYANATE*
• Synonyms: 4-(MALEINIMIDO)PHENYL ISOCYANATE 97+%;1H-Pyrrole-2,5-dione,1-(4-isocyanatophenyl)-(9CI);1-(4-isocyanatophenyl)-1H-pyrrole-2,5-dione;p-MaleiMidophenyl isocynate;N-(p-MaleiMidophenyl)isocyanate(PMPI)
• CAS NO: 123457-83-0
• Molecular Formula: C₁₁H₆N₂O₃
• Molecular Weight: 214.17694
• Product Categories: ISOCYANATE;heteroXlink
• Mol File: 123457-83-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 120-125 °C
• Boiling Point: 375.4°Cat760mmHg
• Flash Point: 180.8°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 7.82E-06mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: 2-8°C
• PKA: -1.58±0.20(Predicted)
• CAS DataBase Reference: 4-(MALEINIMIDO)PHENYL ISOCYANATE*(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(MALEINIMIDO)PHENYL ISOCYANATE*(123457-83-0)
• EPA Substance Registry System: 4-(MALEINIMIDO)PHENYL ISOCYANATE*(123457-83-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 22-36/37-45
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 123457-83-0(Hazardous Substances Data)

Usage

General Description

4-(Maleinimido)Phenyl Isocyanate is a chemical compound known for its reactivity and functionality in various chemical reactions, especially in the field of polymer chemistry. As an isocyanate, it can react with compounds containing alcohol or amine groups to form urethanes and urea. For example, it is often used in the synthesis of polyurethane plastics. The maleinimido group brings another level of reactivity which allows the compound to participate in click reactions, thereby contributing to the creation of complex polymer architectures. Despite its usefulness, this chemical could be slightly hazardous and it should be handled with caution due to its irritant behavior.

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

• 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 
• 17057-04-4 N-(4-carboxyphenyl)maleimide 
• 58174-51-9 N-[4-(azidocarbonyl)phenyl]maleimide 

Downstream Products

• 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 
• 741270-61-1 C₄₀H₃₂N₄O₈ 
• 756902-09-7 N-[p-(2-furfuryl-carbamate)phenylene]maleimide 

Relevant articles and documents

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

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.