2210-24-4

Usage

Uses

Used in Polymer Production:
N-Phenylacrylamide is used as a monomer in the production of polymers for its ability to undergo free radical polymerization, resulting in high molecular weight polymers with diverse applications in various industries.
Used in Copolymer Synthesis:
In the field of polymer chemistry, N-Phenylacrylamide is utilized as a monomer in the synthesis of copolymers, allowing for the creation of materials with tailored properties for specific applications.
Used as a Crosslinking Agent in Hydrogel Production:
N-Phenylacrylamide is employed as a crosslinking agent in the production of hydrogels, which are three-dimensional polymeric networks capable of absorbing and retaining large amounts of water. These hydrogels have potential applications in various fields, including drug delivery, tissue engineering, and biomaterials.
Used in Drug Delivery:
Due to its properties, N-Phenylacrylamide has potential applications in drug delivery systems, where it can be used to create hydrogels or other polymeric structures for the controlled release of therapeutic agents.
Used in Tissue Engineering and Biomaterials:
N-PHENYLACRYLAMIDE's ability to form hydrogels and its compatibility with biological systems makes N-Phenylacrylamide a candidate for use in tissue engineering and the development of biomaterials for medical applications.
However, it is crucial to handle N-Phenylacrylamide with caution, as it is a known irritant and sensitizer, and appropriate safety measures should be taken during its use in research and industrial settings.

InChI:InChI=1/C9H9NO/c1-2-9(11)10-8-6-4-3-5-7-8/h2-7H,1H2,(H,10,11)

Upstream product

• 66223-76-5 N-phenyl hydroxy-3 propanamide 
• 79888-54-3 β-anilinopropionic acid anilide 
• 3460-04-6 3-chloro-N-phenylpropionamide 
• 62-53-3 aniline 
• 74-86-2 acetylene 
• 61245-07-6 2',2'-dimethyl-spiro[bicyclo[2.2.1]hept-5-ene-2,5'-[1,3]dioxane]-4',6'-dione 
• 74-85-1 ethene 
• 103-71-9 phenyl isocyanate 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 107-13-1 acrylonitrile 
• 5679-59-4 diphenylphosphazoanilide 
• 79-10-7 acrylic acid 
• 56-23-5 tetrachloromethane 
• 108-88-3 toluene 

Downstream Products

• 115422-39-4 4-Benzyloxycarbonylamino-4,4-diaethoxycarbonyl-buttersaeure-anilid 
• 42003-72-5 Diethyl-N-phenyl-P-<2-(phenylcarbamoyl)ethyl>-phosphonimidat 
• 57181-28-9 2-Chloro-3-[4-(4-chloro-benzyloxy)-phenyl]-N-phenyl-propionamide 
• 51761-58-1 Dibutyl-N-phenyl-P-<2-(phenylcarbamoyl)ethyl>-phosphonimidat 
• 4641-51-4 γ-Methylsulfin-butyranilid 
• 73840-08-1 S-[2-(N-Phenylcarbamoyl)-aethyl]-isothioharnstoff 
• 57181-56-3 N-phenyl-2-chloro-3-[4-(1-phenylethyloxy)phenyl]propionamide 
• 20591-37-1 2-hexendicarboxylic acid dianilide 
• 22080-65-5 3-(Diphenylphosphinyl)-propionanilid 
• 118655-43-9 bis-(2-phenylcarbamoyl-ethyl)-malonic acid diethyl ester 
• 56051-98-0 heptananilide 
• 80188-12-1 2-methyl-N-phenylbut-3-enamide 
• 108811-81-0 1,4,5,6,7,7-Hexabromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid phenylamide 
• 74590-90-2 2,3-dihydro-2-methyl-2-(N-phenylbut-2-en-4-amide)-1H-indole 

Relevant academic research and scientific papers

Probing the influence of polymer architecture on liquid-liquid phase transitions of aqueous poly(N,N-dimethylacrylamide) copolymer solutions

Thermosensitive poly(N,N-dimethylacrylamide-co-N-phenylacrylamide) (DMA-co-PhAm) copolymers were prepared by atom transfer radical polymerization (ATRP) in methanol/water mixtures at room temperature with methyl 2-chloropropionate as the initiator and CuCl/Me6TREN as the catalyst. The resultant DMA-co-PhAm copolymers had tailored compositions and controlled molecular weights, and their aqueous solutions underwent liquid-liquid phase separation upon heating. These phase transition temperatures, measured by the cloud point method, were dependent on polymer concentrations, compositions, and molecular weights. The efficiency of the thermally induced liquid-liquid phase transition, i.e., the yield of phase-separated polymer, increased with increasing solution temperature, suggesting this thermally induced liquid-liquid phase transition to be a continuous equilibrium process. The efficiency of phase separation could be enhanced by adding NaCl to the solution.

Bromo Radical-Mediated Photoredox Aldehyde Decarbonylation towards Transition-Metal-Free Hydroalkylation of Acrylamides at Room Temperature

Herein, we report a visible-light-mediated hydroalkylation reaction of alkenes using easily available aldehydes as alkyl sources via bromo radical-promoted photoredox decarbonylation. This protocol provides an alternative entry to C(sp3)?C(sp3) bond formation and features considerable advantages including mild and clean reaction conditions, obviation for transition-metal catalyst, and good functional group compatibility.

Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides

The asymmetric transfer hydrogenation (ATH) of α-keto-1,4-diamides using a tethered Ru/TsDPEN catalyst was achieved in high ee. Studies on derivatives identified the structural elements which lead to the highest enantioselectivities in the products. The α-keto-amide reduction products have been converted to a range of synthetically valuable derivatives.

Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins

A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical. Strain-induced ring opening and intermolecular addition to the olefin generate an intermediate carbon-centered radical that is reduced to an anion prior to 5-exo cyclization. This enables a highly diastereoselective construction of trans-cyclopentanes possessing synthetically useful functional groups.

Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions

The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.

LiCl-promoted amination of β-methoxy amides (γ-lactones)

An efficient and mild method has been developed for the amination of β-methoxy amides (γ-lactones) including natural products michelolide, costunolide and parthenolide derivatives by using lithium chloride in good yields. This reaction is applicable to a wide range of substrates with good functional group tolerance. Mechanism studies show that the reactions undergo a LiCl promoted MeOH elimination from the substrates to form the corresponding α,β-unsaturated intermediates followed by the Michael addition of amines.

Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes

Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.

An efficient approach for the synthesis of new (±)-coixspirolactams

Coixspirolactams, spiro[oxindole-γ-lactones], are found in adlay seeds and exhibit anticancer activity. A novel synthetic methodology was developed to enable an easy access to (±)-coixspirolactam A and a large number of new coixspirolactams in excellent overall yields. The exquisite exploitation of formamide reactivity was essential for the construction of oxindole and lactone scaffolds. This journal is

Discovery of secondary sulphonamides as IDO1 inhibitors with potent antitumour effects in vivo

Indoleamine 2,3-dioxygenase 1 (IDO1) as a key rate-limiting enzyme in the kynurenine pathway of tryptophan metabolism plays an important role in tumour immune escape. Herein, a variety of secondary sulphonamides were synthesised and evaluated in the HeLa cell-based IDO1/kynurenine assay, leading to the identification of new IDO1 inhibitors. Among them, compounds 5d, 5l and 8g exhibited the strongest inhibitory effect with significantly improved activity over the hit compound BS-1. The in vitro results showed that these compounds could restore the T cell proliferation and inhibit the differentiation of na?ve CD4+ T cell into highly immunosuppressive FoxP3+ regulatory T (Treg) cell without affecting the viability of HeLa cells and the expression of IDO1 protein. Importantly, the pharmacodynamic assay showed that compound 5d possessed potent antitumour effect in both CT26 and B16F1 tumours bearing immunocompetent mice but not in immunodeficient mice. Functionally, subsequent experiments demonstrated that compound 5d could effectively inhibit tumour cell proliferation, induce apoptosis, up-regulate the expression of IFN-γ and granzyme B, and suppress FoxP3+ Treg cell differentiation, thereby activate the immune system. Thus, compound 5d could be a potential and efficacious agent for further evaluation.

Polysubstituted tryptamine benzamide compound and preparation method and application thereof

The invention discloses a polysubstituted tryptamine benzamide compound and a preparation method and application thereof. The compound is characterized in that the compound is a polysubstituted tryptamine benzamide compound with a structural formula shown as a formula I or a pharmaceutically acceptable salt, ester or solvate of the polysubstituted tryptamine benzamide compound with the structuralformula shown as the formula I. The preparation method comprises the following steps: (1) carrying out amide synthesis reaction on a compound shown in a formula II and a compound shown in a formula III to obtain a compound shown in a formula IV; and (2) reacting the compound as shown in the formula IV with V to carry out Michael addition reaction so as to obtain a compound as shown in the formulaI. The polysubstituted tryptamine benzamide compound and a preparation method and application thereof have the advantages that tumor growth can be effectively inhibited, so that growth stagnation, differentiation or apoptosis of tumor cells is induced, and the effect of inhibiting tumor cell proliferation is achieved.