10537-12-9

Usage

Uses

Used in Organic Synthesis:
9-Phenyl-9,10-dihydroacridine is used as a building block in organic synthesis for the preparation of various heterocyclic compounds. Its unique structure allows for the creation of a wide range of chemical entities, making it a valuable component in the development of new molecules with diverse applications.
Used in Pharmaceutical and Agrochemical Synthesis:
As a starting material, 9-Phenyl-9,10-dihydroacridine is employed in the synthesis of pharmaceuticals and agrochemicals. Its versatile chemical properties enable the development of new drugs and agrochemicals with improved efficacy and selectivity.
Used in Electronic Devices:
Due to its interesting electrochemical properties, 9-Phenyl-9,10-dihydroacridine is potentially useful in the development of materials for electronic devices. Its unique structure and properties can contribute to the advancement of electronic components and systems.
Used in Organic Light-Emitting Diodes (OLEDs):
9-Phenyl-9,10-dihydroacridine's photophysical properties make it a promising candidate for the development of materials used in organic light-emitting diodes. Its ability to emit light upon electrical stimulation can enhance the performance and efficiency of OLEDs, leading to improved display and lighting technologies.

InChI:InChI=1/C19H15N/c1-2-8-14(9-3-1)19-15-10-4-6-12-17(15)20-18-13-7-5-11-16(18)19/h1-13,19-20H

Upstream product

• 260-94-6 acridine 
• 591-51-5 phenyllithium 
• 602-56-2 9-phenylacridine 
• 408315-87-7 9-(2-iodo-phenyl)-9,10-dihydro-acridine 
• 4051-56-3 N,N-diphenylbenzamide 
• 65-85-0 benzoic acid 
• 98-07-7 Benzotrichlorid 
• 122-39-4 diphenylamine 
• 857614-19-8 9-(2-iodo-phenyl)-acridine 
• 88-67-5 2-Iodobenzoic acid 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 

Downstream Products

• 102949-21-3 10-benzyl-9-phenyl-(9,10-dihydroacridine) 
• 56875-26-4 10-methyl-9-phenyl-9,10-dihydroacridine 
• 602-56-2 9-phenylacridine 
• 1352136-04-9 4,9-diphenylacridine 
• 1352136-28-7 9-phenyl-4-(2-tolyl)acridine 
• 123607-36-3 10-methyl-9-phenyl-acridinium; chloride-monohydrate 

Relevant academic research and scientific papers

Zincate-Mediated Arylation Reactions of Acridine: Pre- and Postarylation Structural Insights

This study explores the synthetic utility of homo(aryl) lithum zincate reagents [LiZnPh3] (2) and [Li2ZnPh4] (3), made by cocomplexation of variable amounts of their monometallic components LiPh and ZnPh2 (1), as chemoselective nucleophilic arylating reagents. Lithium zincates 2 and 3 were both characterized by multinuclear (1H, 13C, and 7Li) NMR spectroscopy, and in the case of 2, a classical reagent in heterobimetallic chemistry, the molecular structure of its OnBu2 solvate [LiZnPh3(OnBu2)2] 2·2OBu2 has been established by X-ray crystallography. Using the synthetically relevant N-heterocyclic molecule acridine (acr, NC13H9), a new zincate-mediated arylating approach is demonstrated which allows the chemoselective arylation of acr at its C9 position, affording 9,10-dihydro-9-phenylacridine (4) in 95% yield using microwave irradiation (125 °C, 20 min). These conditions are in contrast with previous transition-metal-catalyzed methodologies using ZnPh2 as an arylating reagent, which require significantly longer reaction times (130 °C, 20 h). Oxidation of 4 with DDQ furnished 9-phenylacridine (5) in a 71% yield. New insights into the constitution of the intermediate organometallic species involved in these reactions prior to the hydrolysis step have been gained by trapping homometallic [(THF)3Li(NC13H9-Ph)] (6). Interestingly the reaction of acr with 3 equiv of PhLi/TMEDA led to the isolation of a different product, namely the novel paramagnetic [(THF)(TMEDA)Li{NC13H8-Ph}?-] (7), which contains a radical anion of 9-phenylacridine. The structure of the donor-acceptor complex [(acr)ZnPh2] (8) has also been included as a result of the reaction of 1 with acr. (Chemical Presented).

Selective Catalytic Hydrogenation of Heteroarenes with N-Graphene-Modified Cobalt Nanoparticles (Co3O4-Co/NGratα-Al2O3)

Cobalt oxide/cobalt-based nanoparticles featuring a core-shell structure and nitrogen-doped graphene layers on alumina are obtained by pyrolysis of Co(OAc)2/phenanthroline. The resulting core-shell material (Co3O4-Co/NGratα-Al2O3) was successfully applied in the catalytic hydrogenation of a variety of N-heteroarenes including quinolines, acridines, benzo[h], and 1,5-naphthyridine as well as unprotected indoles. The peculiar structure of the novel heterogeneous catalyst enables activation of molecular hydrogen at comparably low temperature. Both high activity and selectivity were achieved in these hydrogenation processes, to give important building blocks for bioactive compounds as well as the pharmaceutical industry.

Direct regioselective phenylation of acridine derivatives by phenyllithium

Acridine and acridine derivatives have been converted directly to phenyl derivatives regioselectively using phenyllithium.

Reduction of 9-substituted acridines with nickel-aluminum alloy

9-Methyl-, 9-ethyl-, 9-propyl-, 9-isopropyl-, and 9-phenylacridines were treated with nickel-aluminum alloy in hydrochloric acid to give the corresponding 1,2,3,4,5,6,7,8-octahydroacridines and 9,10-dihydroacridines. The yields are dependent upon the C-9

The Reductive Metalation of 9-Phenylacridine

The reductive metalation of 9-phenylacridine by sodium to a dianion is described and the reactions of the dianion with electrophiles investigated.Reactions of the dianion with methanol, dimethyl sulfate, X(CH2)nX (n = 2,3,4, X = Cl, Br), and me