143629-26-9

Basic information

• Product Name: N-(4-hydroxyphenyl)-MaleaMic acid
• Synonyms: N-(4-hydroxyphenyl)-MaleaMic acid;(Z)-4-((4-Hydroxyphenyl)aMino)-4-oxobut-2-enoic acid
• CAS NO: 143629-26-9
• Molecular Formula: C₁₀H₉NO₄
• Molecular Weight: 207.18276
• EINECS: -0
• Mol File: 143629-26-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-hydroxyphenyl)-MaleaMic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-hydroxyphenyl)-MaleaMic acid(143629-26-9)
• EPA Substance Registry System: N-(4-hydroxyphenyl)-MaleaMic acid(143629-26-9)

Safety Data

• Hazardous Substances Data: 143629-26-9(Hazardous Substances Data)

Usage

Uses

Used in Materials Science:
N-(4-hydroxyphenyl)-MaleaMic acid is used as a building block for the synthesis of polymers due to its ability to form polymers, contributing to the development of new materials with enhanced properties.
Used in Pharmaceutical Industry:
N-(4-hydroxyphenyl)-MaleaMic acid is used as a precursor in the synthesis of pharmaceutical compounds, leveraging its chemical structure to create new drugs with potential therapeutic benefits.
Used in Antioxidant Applications:
N-(4-hydroxyphenyl)-MaleaMic acid is used as an antioxidant, capitalizing on its antioxidant properties to protect against oxidative stress and related conditions in various applications, including health supplements and cosmetic products.
Used in Organic Synthesis:
N-(4-hydroxyphenyl)-MaleaMic acid is used as an intermediate in organic synthesis, serving as a key component in the production of other organic compounds for a range of applications across different industries.

Upstream product

• 108-31-6 maleic anhydride 
• 123-30-8 4-amino-phenol 
• 67-64-1 acetone 
• 71-43-2 benzene 

Downstream Products

• 6637-46-3 4-(acetoxyphenyl)maleimide 
• 906352-14-5 N-p-acetoxy-phenylisomaleimide 
• 7300-91-6 N-(4-hydroxyphenyl)maleimide 
• 915711-53-4 (E)-3-(4-Hydroxy-phenylcarbamoyl)-acrylic acid methyl ester 
• 915711-45-4 (Z)-3-(4-Hydroxy-phenylcarbamoyl)-acrylic acid methyl ester 

Relevant articles and documents

Solvent free preparation of n-substituted maleanilic acid

Six N-maleanilic acids namely N-(4-carboxy)maleanilic acid (CAMAA), N-(4- bromo)maleanilic acid (BMAA), N-(4-hydroxy)maleanilic acid (HMAA), N-(3-hydroxy)maleanilic acid (mHMAA), N-(4-chloro)maleanilic acid (CMAA) and N-(4-methyl)maleanilic acid (MMAA) we

Development of polymeric phase change materials on the basis of diels-alder chemistry

Diels-Alder (DA) chemistry is increasing popular due to its simplicity and efficiency; however, one concept that has yet to be thoroughly explored is incorporation of DA linkages within materials for the development of polymeric phase change materials. It is well established that the retro-DA reaction results in a large endotherm, which could be a potential energy sink for phase change materials. Hydroxyl-terminated polybutadiene (HTPB) was selected as a prepolymer and modified with different DA linkages. Cured materials were prepared upon addition of diisocyanates and their physical properties of the cured elastomers were investigated using thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and rheological testing. The resulting thermally responsive HTPB (TR-HTPB) exhibited the ability to absorb energy and flow at elevated temperatures. Furthermore, they displayed unusual responses to repeated thermal cycling, including changes in thermal absorption and rheological characteristics.

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.

Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

A facile and economical procedure for the synthesis of maleimide derivatives using an acidic ionic liquid as a catalyst

Seven maleimide derivatives were synthesized in good yields and high purity from the corresponding maleamic acids using a Bronsted acidic room temperature ionic liquid (RTIL) as a catalyst. The products were obtained through merely a decanting and removal of the solvent, suggesting that this procedure is superior to the conventional routes, in which the strong organic/inorganic acids were used as the catalysts, as well as a complicated post-processing procedure for the separation and purification of the products was employed.

Synthesis and characterization of schiff base metal complexes and reactivity studies with malemide epoxy resin

A novel malemide epoxy containing Co(II), Ni(II) and Cu(II) ions have been synthesized by curing malemide epoxy resin (MIEB-13) and Co(II), Ni(II) and Cu(II) complexes of macrocyclic bis-hydrazone Schiff base. The Schiff base was synthesized by reacting 1,4-dicarbnyl phenyl dihydrazide with 2,6-diformyl-4-methyl phenol. The Schiff base and its Co(II), Ni(II) and Cu(II) complexes have been characterized by elemental analyses, spectral (IR, 1H NMR, UV-vis., FAB mass, ESR), thermal and magnetic data. The curing reaction of maleimide epoxy compound with metal complexes was studied as curing agents. The stability of cured samples was studied by thermo-gravimetric analyses and which have excellent chemical (acid/alkali/solvent) and water absorption resistance. Further, the scanning electron microscopy (SEM) and definitional scanning colorimetric (DSC) techniques were confirmed the phase homogeneity of the cured systems.

Reactivity studies of maleimide epoxy resin with long chained amines

After phenylmaleimido group was successfully incorporated into bisphenol-A type epoxy resins (B-13 ) to result in compound possessing both oxirane ring and maleimide reactive groups. The cured maleimide epoxy samples are obtained by thermally curing of the maleimide epoxy (MIE) compounds with aliphatic long chained amines such as Tetraethylenepentamine (TEPA), Bishexamethylenetriamine (BHMT), 2-methyl pentamethylenediamine (2-MPMDA) and 2,2,4-trimethy diamines (2,2,4-TMDA) exhibited excellent thermal stability and good chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.

Synthesis of co(II), Ni(II) and Cu(II) complexes from schiff base ligand and reactivity studies with thermosetting epoxy resin

A hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) containing Co(II), Ni(II) and Cu(II) ions was prepared by curing N-MPGE and tetradentate Schiff base Co(II), Ni(II) and Cu(II) complexes. The curing polymerization reaction of N-MPGE with metal complexes as curing agents was studied. The cured samples were studied for thermal stability, chemical (acid/alkali/solvent) and water absorption resistance and homogeneity of the cured systems. The tetradentate Schiff base, 3-[(Z)-2-piperazin-1-yl- ethylimino]-1,3-dihydro indol-2-one was synthesized by the condensation of Isatin (Indole-2, 3-dione) with 1-(2-aminoethyl)piperazine (AEP). Its complexes with Co(II), Ni(II) and Cu(II) have been synthesized and characterized by microanalysis, conductivity, Uv-Visible, FT-IR, TGA and magnetic susceptibility measurements. The spectral data revealed that the ligand acts as a neutral tetradentate Schiff base and coordinating through the azomethine nitrogen, two piperazine nitrogen atoms and carbonyl oxygen.

Preparation and reactivity studies of maleimidophenyl glycidylether with amines

The hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) was prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possessed both the oxirane ring and maleimide group. The curing reaction of N-MPGE with amines as curing agents such as tetraethylenepentamine (TEPA), bishexamethylenetriamine (BHMT), 2-methyl pentamethylenediamine (2-MPMDA) and 2,2,4-trimethy diamines (2,2,4-TMDA) was studied. The cured samples exhibited good thermal stability and excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity network of the cured systems.