4814-74-8

Basic information

• Product Name: N-Hydroxymaleimide
• Synonyms: N-HYDROXYMALEAMINE;N-HYDROXYMALEIMIDE;1-HYDROXY-2,5-DIHYDRO-1H-PYRROLE-2,5-DIONE;1-hydroxy-1H-pyrrole-2,5-dione;N-Hydroxymaleimide 95%;1-Hydroxypyrrole-2,5-dione;1-Hydroxy-3-pyrroline-2,5-dione;N-Hydroxymaleimide,97%
• CAS NO: 4814-74-8
• Molecular Formula: C₄H₃NO₃
• Molecular Weight: 113.07
• EINECS: 225-385-4
• Product Categories: Miscellaneous;Heterocyclic Compounds;Heterocycles;Active Esters/Additives;Active Esters/AdditivesSynthetic Reagents;Coupling;Peptide Synthesis
• Mol File: 4814-74-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 130-133 °C (dec.)(lit.)
• Boiling Point: 211.74°C (rough estimate)
• Flash Point: 121.2 °C
• Appearance: yellow to brown crystalline powder
• Density: 1.5808 (rough estimate)
• Vapor Pressure: 0.000581mmHg at 25°C
• Refractive Index: 1.4543 (estimate)
• Storage Temp.: 2-8°C
• PKA: 6.44±0.20(Predicted)
• BRN: 1524594
• CAS DataBase Reference: N-Hydroxymaleimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hydroxymaleimide(4814-74-8)
• EPA Substance Registry System: N-Hydroxymaleimide(4814-74-8)

Safety Data

• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4814-74-8(Hazardous Substances Data)

Usage

Description

N-Hydroxymaleimide, with the CAS number 4814-74-8, is a yellow to brown crystalline powder that serves as a valuable compound in the realm of organic synthesis. Its unique chemical properties make it a versatile building block for the creation of various complex molecules and pharmaceuticals.

Uses

Used in Organic Synthesis:
N-Hydroxymaleimide is used as a synthetic building block for the development of complex organic molecules. Its chemical properties allow it to be a key component in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
N-Hydroxymaleimide is used as an intermediate in the synthesis of various pharmaceutical compounds. Its reactivity and structural features make it a valuable asset in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
N-Hydroxymaleimide is also utilized as a starting material for the production of agrochemicals, such as pesticides and herbicides. Its role in these applications is to provide the necessary structural elements for the active ingredients in these products.
Used in Specialty Chemicals:
N-Hydroxymaleimide finds application in the production of specialty chemicals, which are tailored for specific industries and applications. Its versatility in organic synthesis makes it a valuable resource for creating unique and specialized chemical products.

InChI:InChI=1/C4H3NO3/c6-3-1-2-4(7)5(3)8/h1-2,8H

Upstream product

• 60361-89-9 Carbonic acid 2,5-dioxo-2,5-dihydro-pyrrol-1-yl ester phenyl ester 
• 58936-19-9 benzyl N-maleimidyl carbonate 
• 5596-17-8 exo‐N‐hydroxy‐7‐oxabicyclo[2.2.1]hept‐5‐ene‐2,3‐dicarboximide 

Downstream Products

• 90108-77-3 1-carbophenoxy-N-hydroxy-1H-naphth<2,3-d>imidazole-6,7-dicarboximide 
• 138197-84-9 3-(phenylthio)maleimide 
• 138197-85-0 3-(4-Bromo-phenylsulfanyl)-pyrrole-2,5-dione 
• 124552-54-1 3-Phenyl-propionic acid 2,5-dioxo-2,5-dihydro-pyrrol-1-yl ester 

Relevant articles and documents

Thermodynamic and kinetic study of Diels–Alder reaction between furfuryl alcohol and N-hydroxymaleimides — An assessment for materials application

The study of Diels–Alder reactions in materials science is of increasing interest. The main reason for that is the potential thermoreversibility of the reaction. Aiming to predict the behavior of a material modified with maleimido and furyl moieties, 1H NMR and UV-Vis solution studies of the Diels–Alder reaction between furfuryl alcohol and two N-hydroxymaleimides are explored in the present study. Rate constants, activation energy, entropy, and enthalpy of formation were determined from each technique for both reacting systems. Endo and exo isomers were distinguished in 1H NMR, and the transition from a kinetic, controlled Diels–Alder reaction to a thermodynamic one could be observed in the temperature range studied. A discussion on the effect of that on the application in a material was performed. The approach selected considers a simplified equilibrium of the Diels–Alder reaction as the kinetic model, allowing materials scientists to evaluate the suitability of using the reacting molecules for the creation of thermoresponsive materials. The proposed approach determines the kinetic constants without the direct influence of the equilibrium constant value, thereby allowing a more objective data analysis. The effects of the selection of kinetic model, analytical method, and data treatment are discussed.

Synthesis of N-Hydroxymaleimide and N-Hydroxyitaconimide and their Related Derivatives

Thermolysis of alkyl and aryl carbonates of N-hydroxy-3,6-epoxy-1,2,3,6-tetrahydrophthalimide yielded the corresponding alkyl or aryl N-maleimidyl carbonates.The benzyl or phenyl carbonate afforded N-hydroxymaleimide, either by treatment with trifluoroacetic acid or by refluxing in methanol.N-hydroxyitaconimide was obtained by dehydration of N-hydroxyitaconamic acid with dicyclohexylcarbodi-imide (DCC).The DCC dehydration of N-acetoxy- and N-benzyloxy-itaconamic acids produced iminofuranones, which could be rearranged to imides.Deacylation of N-acetoxymaleimide was unsuccessful, whereas aminolysis of N-acetoxyitaconimide yielded the N-hydroxyimide.