52536-39-7

Usage

Uses

Used in Pharmaceutical Industry:
2-PROP-2-YNYLOXY-PHENYLAMINE is used as a key intermediate for the synthesis of various pharmaceuticals, enabling the development of new drugs with improved therapeutic properties and efficacy.
Used in Agrochemical Industry:
2-PROP-2-YNYLOXY-PHENYLAMINE is used as a key intermediate in the production of agrochemicals, contributing to the development of innovative and effective solutions for crop protection and pest management.
Used in Advanced Materials Development:
2-PROP-2-YNYLOXY-PHENYLAMINE is used as a building block for the creation of novel organic molecules, playing a crucial role in the development of advanced materials with unique properties and applications in various industries.
Used in Organic Synthesis:
2-PROP-2-YNYLOXY-PHENYLAMINE is used as a key intermediate in organic synthesis, facilitating the synthesis of diverse organic compounds and contributing to the discovery of new chemical entities with potential applications in various fields.

Upstream product

• 13350-09-9 1-nitro-2-(prop-2-yn-1-yloxy)benzene 
• 88-75-5 2-hydroxynitrobenzene 
• 614-80-2 2-(acetylamino)phenol 
• 95-55-6 2-amino-phenol 
• 186663-74-1 tert-butyl (2-hydroxyphenyl)carbamate 
• 98-09-9 benzenesulfonyl chloride 
• 6165-75-9 propargyl benzenesulfonate 

Downstream Products

• 52536-40-0 2-(3-phenylprop-2-ynyloxy)aniline 
• 326598-59-8 1,2-bis[(3'-phenyl-2'-ynyloxy)-2'-amino-phenyl]benzene 
• 326598-56-5 2-[3-(4-methylphenyl)prop-2-ynyloxy]aniline 
• 326598-55-4 2-[3-(3-chloro-phenyl)-prop-2-ynyloxy]-phenylamine 
• 1350705-08-6 2-ethoxycarbonyl-3-(4-fluorophenyl)-4H-pyrazolo[5,1-c][1,4]benzoxazine 
• 1350705-11-1 2-ethoxycarbonyl-3-(2-methyl-4-nitrophenyl)-4H-pyrazolo[5,1-c]-[1,4]benzoxazine 
• 1350705-12-2 2-ethoxycarbonyl-3-(4-carbomethoxyphenyl)-4H-pyrazolo[5,1-c]-[1,4]benzoxazine 
• 52536-38-6 chloro-[2-(3-phenyl-prop-2-ynyloxy)-phenylhydrazono]-acetic acid ethyl ester 
• 1610804-89-1 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4-dimethoxybenzamide 
• 1610804-86-8 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-methoxybenzamide 
• 1610804-87-9 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-methoxybenzamide 
• 1610804-88-0 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-4-methoxybenzamide 
• 1610804-85-7 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)benzamide 
• 1610804-90-4 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,5-dimethoxybenzamide 

Relevant academic research and scientific papers

Ruthenium-Catalyzed Tandem Carbene/Alkyne Metathesis/N-H Insertion: Synthesis of Benzofused Six-Membered Azaheterocycles

The Cp*RuCl-based catalyst enables expedient access to a variety of benzofused six-membered azaheterocycles from unprotected o-alkynylanilines and trimethylsilyldiazomethane through an unprecedent tandem carbene/alkyne metathesis/N-H insertion reaction. The transformation takes place under mild reaction conditions (room temperature, 15 min) and with excellent functional group tolerance. The synthetic utility of the final products and a mechanistic rationale are also discussed.

Self-Assembled Magnetic Gold Catalysts from Dual-Functional Boron Clusters

A new class of core–shell magnetic gold nanocomposites is prepared in a raspberry-like fashion by the controlled supramolecular host–guest assembly of γ-cyclodextrins (γ-CDs) and boron clusters. In this work, Cs2[closo-B12H12], a fundamental boron cluster, can play a dual role in the preparation of highly monodispersed Au nanoparticles and in the immobilization of Au nanoparticles on the γ-CDs@Fe3O4 surface as an effective anchor. This facile and spontaneous supramolecular strategy allows for the control of the size and composition of the highly stable gold composites. Furthermore, the obtained AuNPs@Fe3O4 composites exhibit an excellent catalytic activity and recyclability for the selective reduction of nitroaromatics to their corresponding aniline compounds, and the fastest reaction can be achieved within 20 s with a high conversion and selectivity at room temperature, which is better than that obtained previously in studies on metal nanoparticle composites as catalysts.

Gold nanoparticles anchored onto the magnetic poly(ionic-liquid) polymer as robust and recoverable catalyst for reduction of Nitroarenes

Gold nanoparticles supported on poly ionic-liquid magnetic nanoparticles (MNP@PIL@Au) were synthesized by reduction of HAuCl4 with sodium borohydride. The synthesized catalyst was characterized using by AAS, TEM, FT-IR, EDS, TGA and XRD techniques. The performance of the synthesized catalyst was investigated in the reduction of nitroarenes with NaBH4. The reaction was carried out for various nitroarenes in water and mild conditions with high yields. The catalyst selectivity for the reduction of nitro group in the presences of other functional groups such as halides and alkynes was fairly well. The recycling of the catalyst was done 8 times without any significant loss of its catalytic activity.

Hexafluoro-2-propanol-assisted quick and chemoselective nitro reduction using iron powder as catalyst under mild conditions

Hexafluoro-2-propanol as the promoter for the quick nitro reduction using a combination of iron powder and 2 N HCl aqueous solution is reported. This methodology has several positive features, as it is of room temperature, remarkably short reaction time. A wide range of substrates including those bearing reducible functional groups such as aldehyde, ketone, acid, ester, amide, nitrile, halogens, even allyl, propargyl and heterocycles are chemoselectively reduced in good to excellent yields, even on gram scale. Notably, the highly selective reduction of 3-nitrophenylboronic acid is achieved quantitatively. The reduction is also tolerant of common protecting groups, and aliphatic nitro compound, 1-nitrooctane can be reduced successfully.

AgNO3Catalyzed Regio-Selective Synthesis of 3-Alkyl/Aryl-idene-3,4-dihydro-4-tosyl-2H-1,4-Benzoxazine: Novel Anti-Tubercular Scaffolds

A facile and efficient method for the construction of 3-alkyl/aryl substituted 1,4-benzoxazine and benzoxazepine via AgNO3catalyzed cyclization of propargyloxy sulfonamides and their anti-tubercular activity against Mycobacterium tuberculosis H37RVis described. This cyclization proceeds through 6-exo-dig manner to generate the products in moderate to good yields.

Design, synthesis and biological evaluation of novel triazole-core reversal agents against P-glycoprotein-mediated multidrug resistance

We designed and synthesized a novel series of P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) inhibitors bearing a triazolphenethyl-tetrahydroisoquinoline scaffold through click chemistry. Then those synthesized compounds were tested on doxorubi

Functionalizable red emitting calcium sensor bearing a 1,4-triazole chelating moiety

Herein we developed a functionalizable OFF-ON red emitting fluorescent calcium probe based on a new chelating system formed by CuAAC click chemistry (Huisgen cycloaddition). The pro-sensor 7 which is not sensitive to Ca2+, contains an alkyne moiety that, upon the click reaction, forms a chelating group involving the 1,4-triazole. Probe 10 exhibited good sensitivity towards calcium (Kd = 5.8 μM) and zinc (5.6 μM) with a high dynamic range (65 fold fluorescence increase), high quantum yield (0.59) and showed very low fluorescence enhancement in the presence of a high concentration of Mg2+. We extended this method and generated two dextran conjugates in order to compare their sensing properties with those of the molecular form of 10.

Cyclizing radical carboiodination, carbotelluration, and carboaminoxylation of aryl amines

Radical carboiodination of various aryl amines is reported. Aryl diazonium salts, generated in situ from the corresponding aryl amines, are reacted with Bu4NI to provide the corresponding aryl radicals which undergo 5-exo or 6-exo cyclization. Iodine abstraction eventually affords the carboiodinated products in good to excellent yields. If TEMPO is added, the cascade provides the cyclized carboaminoxylation products. Running the reaction in the presence of PhTeTePh affords the phenyltellurated cyclized products.

Discovery of novel P-glycoprotein-mediated multidrug resistance inhibitors bearing triazole core via click chemistry

A novel series of P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) inhibitors bearing a triazol-phenethyl-tetrahydroisoquinoline scaffold were designed and synthesized via click chemistry. Most of the synthesized compounds showed higher reversal activity than verapamil (VRP). Among them, the most potent compound 5 showed a comparable activity with the known potent P-gp inhibitor WK-X-34 with lower cytotoxicity (IC50s > 100 μm). Compared with VRP, compound 5 exhibited more potency in increasing drug accumulation in K562/A02 MDR cells. Moreover, compound 5 persisted longer chemo-sensitizing effect (>24 h) than VRP (6 h) with reversibility. Given the low intrinsic cytotoxicity and the potent reversal activity, compound 5 may represent a promising candidate for developing P-gp-mediated MDR inhibitor.

Design, synthesis and evaluation of novel triazole core based P-glycoprotein-mediated multidrug resistance reversal agents

A novel series of triazol-N-ethyl-tetrahydroisoquinoline based compounds were designed and synthesized via click chemistry. Most of the synthesized compounds showed P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) reversal activities. Among them, compound 7 with little cytotoxicity towards GES-1 cells (IC50 >80 μM) and K562/A02 cells (IC50 >80 μM) exhibited more potency than verapamil (VRP) on increasing anticancer drug accumulation in K562/A02 cells. Moreover, compound 7 could significantly reverse MDR in a dose-dependent manner and also persist longer chemo-sensitizing effect than VRP with reversibility. Further mechanism studies revealed that compound 7 in reversing MDR revealed that it could remarkably increase the intracellular accumulation of both rhodamine-123 (Rh123) and adriamycin (ADM) in K562/A02 cells as well as inhibit their efflux from the cells. These results suggested that compound 7 showed more potency than the classical P-gp inhibitor VRP under the same conditions, which may be a promising P-gp-mediated MDR modulator for further development.