719-54-0

Usage

Uses

Used in Pharmaceutical Industry:
10-METHYL-9(10H)-ACRIDONE is used as an intermediate in the synthesis of 9-Mesityl-10-methylacridinium Tetrafluoroborate (M258620), which is a key compound in the production of γ-butyrolactones, γ-lactams, and pyrrolidines. These compounds are important building blocks in the development of pharmaceuticals and have potential applications in the treatment of various diseases.
Used in Chemical Synthesis:
10-METHYL-9(10H)-ACRIDONE is used as a precursor in the synthesis of various chemical compounds through Photoredox Catalysis, a technique that involves the use of light to facilitate chemical reactions. This method has been reported by Nicewicz et al. to mediate a wide range of transformations, including the anti-Markovnikov hydroamination of alkenes, the addition of carboxylic acids to alkenes, and the hydrotrifluoromethylation of styrenes using the Langlois reagent S673690.

InChI:InChI=1/C14H11NO/c1-15-12-8-4-2-6-10(12)14(16)11-7-3-5-9-13(11)15/h2-9H,1H3

Upstream product

• 4217-54-3 9,10-dihydro-10-methylacridine 
• 99586-19-3 benzoic acid-(2,4,6,N-tetrachloro-anilide) 
• 71-43-2 benzene 
• 10228-90-7 9-methoxyacridine 
• 837-43-4 9-cyano-10-methylacridan 
• 66762-83-2 C₂₁H₁₇NO₂ 
• 541-98-0 6-methyl-pyran-2,4-dione 
• 95256-36-3 9,9'-oxy-bis(10-methylacridinium)bis(trifluoromethanesulfonate) 
• 108-86-1 bromobenzene 
• 35472-56-1 N-methyl-anthranilic acid ethyl ester 
• 769-42-6 1,3-dimethylbarbituric acid 
• 13367-81-2 10-methylacridinium cation 
• 61469-95-2 1-methyl-1H-quinoline-2,4-dione 
• 4788-37-8 N-ethyl-N-methylbenzylamine 

Downstream Products

• 46492-10-8 N-Methyl-9-chloracridinium 
• 17014-39-0 2,7-dibromo-10-methylacridine-9(10H)-one 
• 36519-51-4 9-(4-(dimethylamino)phenyl)-10-methyl-4a,9,9a,10-tetrahydroacridin-9-ol 
• 64236-22-2 10-methyl-N-phenylacridine-9(10H)-imine 
• 58658-02-9 10-methyl-2-nitroacridin-9(10H)-one 
• 83413-85-8 4-nitro-10-methyl-9-acridanone 
• 70232-90-5 (10-methyl-10H-acridin-9-ylidene)-p-tolyl-amine 
• 6321-72-8 9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine 
• 19656-33-8 9,10-dihydro-10-methyl-9-phenylmethyleneacridine 
• 17435-19-7 N-methylthioacridone 
• 578-95-0 10H-acridin-9-one 
• 1012-84-6 perchlorobenzoic acid 
• 95256-52-3 9-Isothiocyanato-10-methylacridinium-trifluormethansulfonat 
• 66762-83-2 C₂₁H₁₇NO₂ 

Relevant academic research and scientific papers

A comprehensive spectral, photophysical and electrochemical study of synthetic water-soluble acridones. A new class of pH and polarity sensitive fluorescent probes

A comprehensive spectroscopic, photophysical and electrochemical investigation of N-alkylacridones, their newly synthesised chlorosulfonyl and water-soluble sulfonic acid derivatives has been undertaken in solution at room temperature. The study includes absorption and emission spectra together with quantitative measurements of the deactivation of the first excited singlet state, from which the rate constants for all the decay processes has been obtained. A comparison on the gradual change of the electronic spectral and photophysical properties with the degree of substitution is considered. In addition the electrochemical behavior of the water-soluble acridones at different pH values was obtained by cyclic and differential pulse voltammetry. The oxidation mechanism of disulfonated acridone is found to occur in one consecutive and irreversible charge transfer pH-dependent reaction. The water-soluble acridones were found to display long lifetime values, dependent on the pH and solvent polarity. This opens a door for its use as selective probes for different cellular environment and targets.

CHEMILUMINESCENCE OF 9-METHYLENEACRIDANS IN MICELLAR AND MEMBRANOUS SYSTEMS

Chemiluminescence of a 1,2-dioxetane derived from 9-methylene-10-dodecylacridan was not detected in aqueous solution but was detected in micellar and membranous systems.The quantum yield and the rate of the chemiluminescence decay in the membranous (2C1615G and 2C1630G) system were affected by the chain melting transition.The results indicate that the chemiluminescence is sensitively affected by the microenvironmental effect.

CHEMILUMINESCENCE OF N-METHYL-9-(DICARBOALKOXYMETHYL)ACRIDANES: SUCCESSIVE FORMATION OF TWO 1,2-DIOXETANONE INTERMEDIATES

N-Methyl-9-(dicarboalkoxymethyl)acridanes (5a-c) which have a similar structural moiety to that of firefly luciferin and give an excellent fluorescent product were found to be chemiluminescent when being oxidized by molecular oxygen in DMSO in the presence of t-BuOK at 70 degC.

Laser Flash Photolysis and Product Studies of the Photoionization of N-Methylacridan in Aqueous Solution

Photolysis of N-methylacridan (1) in deaerated aqueous CH3CN solution results in photoionization, to give the N-methylacridan radical cation (1.+) as the first-formed intermediate.Subsequent deprotonation from 1.+ gives N-methylacridyl (1.), which dimerizes to give 9,9'-bis(N-methylacridyl) (2) as the only isolable product.Quantum yields for loss of 1 are 0.085 and 0.022 in 1:1 H2O-CH3CN and 100percent CH3CN, respectively.In the presence of oxygen, 1. is believed to be oxidized further (electron transfer to O2), to give N-methylacridinium ion (4), which was detected by its characteristic UV absorption and fluorescence emission spectra.Laser flash photolysis studies provide direct evidence for photoionization of 1 to give the radical cation 1.+ which subsequently deprotonates to form 1..The combined transient and product studies indicate a monophotonic mechanism from the first excited state.The results demonstrate that photoexcited 1 is an excellent electron donor to bulk solvent.The process does not require externally added electron acceptors for photoredox chemistry.

New acridone-and (Thio)xanthone-derived 1,1-donor–acceptor-substituted alkenes: Ph-dependent fluorescence and unusual photooxygenation properties

A synthetic route to new heterocyclic 1,1-donor–acceptor-substituted alkenes starting with N-methyl-acridone, xanthone, and thioxanthone was investigated, leading to the acridone-and xanthone-derived products methyl 2-methoxy-2-(10-methylacridin-9 (10H)-ylidene)acetate (7) and methyl 2-methoxy-2-(9H-xanthen-9-ylidene)acetate (10) in low yields with the de-methoxylated product methyl 2-(10-methylacridin-9 (10H)-ylidene)acetate (8) and the reduced compound methyl 2-methoxy-2-(9H-xanthen-9-yl)acetate (11) as the major products from N-methyl acridone and xanthone. From thioxanthone, only the rearrangement and reduction products (14) and (15) resulted. The photophysical properties of compounds (7), (8), and (10) were investigated in the presence and absence of the Br?nsted acid TFA by NMR, UV–VIS absorption, and fluorescence spectroscopy. Protonation of the acridone-derived alkenes (7) and (8) led to strong bathochromic and hyperchromic fluorescence shifts and a substantial increase in Stokes shift. The photooxygenation experiments with these substrates showed an unusual reactivity pattern in the singlet oxygen processes: whereas the electron-rich enolether (7) was chemically unreactive, (8) and (10) were oxidatively cleaved, presumably via intermediate 1,2-dioxetanes.

Photochemical oxidation of a manganese(III) complex with oxygen and toluene derivatives to form a manganese(V)-Oxo complex

Visible light photoirradiation of an oxygen-saturated benzonitrile solution of a manganese(III) corrolazine complex [(TBP8Cz)MnIII] (1): [TBP8Cz = octakis(p-tert-butylphenyl)corrolazinato3-] in the presence of toluene derivatives resulted in formation of the manganese(V)-oxo complex [(TBP8Cz)MnV(O)]. The photochemical oxidation of (TBP8Cz)MnIII with O 2 and hexamethylbenzene (HMB) led to the isosbestic conversion of 1 to (TBP8Cz)MnV(O), accompanied by the selective oxidation of HMB to pentamethylbenzyl alcohol (87%). The formation rate of (TBP 8Cz)MnV(O) increased with methyl group substitution, from toluene, p-xylene, mesitylene, durene, pentamethylbenzene, up to hexamethylbenzene. Deuterium kinetic isotope effects (KIEs) were observed for toluene (KIE = 5.4) and mesitylene (KIE = 5.3). Femtosecond laser flash photolysis of (TBP8Cz)MnIII revealed the formation of a tripquintet excited state, which was rapidly converted to a tripseptet excited state. The tripseptet excited state was shown to be the key, activated state that reacts with O2 via a diffusion-limited rate constant. The data allow for a mechanism to be proposed in which the tripseptet excited state reacts with O2 to give the putative (TBP8Cz)Mn IV(O2?-), which then abstracts a hydrogen atom from the toluene derivatives in the rate-determining step. The mechanism of hydrogen abstraction is discussed by comparison of the reactivity with the hydrogen abstraction from the same toluene derivatives by cumylperoxyl radical. Taken together, the data suggest a new catalytic method is accessible for the selective oxidation of C-H bonds with O2 and light, and the first evidence for catalytic oxidation of C-H bonds was obtained with 10-methyl-9,10-dihydroacridine as a substrate.

Chemiluminescence in Model Membrane Structures. Chemiluminescence of Lucigenin in the Presence of Mg(OH)2 and Benzyl Alcohol. Temperature Effects

The quantum yields of the lucigenin light reaction in didodecyldimethylammonium bromide (DDAB) are affected by the presence of Mg(OH)2; a 35percent increase is observed in lamellar and a 65percent increase in vesicular aggregates.The system is insensitive to benzyl alcohol.The quantum yields in DDAB versus those in water, as a function of temperature show a slope change in the region of the phase transition in lamellar aggregates.This effect is far less pronounced in vesicular aggregates.In contrast to the DDAB aggregates, anionic sodium dimethyldidodecylphosphate (SDDP) sonicated aggregates are associated with lower quantum yields and no apparent slope change in the region of the phase transition. - Keywords: Chemiluminescence; Lucigenin; Membranes

Photocatalytic oxygenation of 10-methyl-9,10-dihydroacridine by O 2 with manganese porphyrins

Photocatalytic oxygenation of 10-methyl-9,10-dihydroacridine (AcrH 2) by dioxygen (O2) with a manganese porphyrin [(P)Mn III: 5,10,15,20-tetrakis-(2,4,6-trimethylphenyl) porphinatomanganese(III) hydroxide [(TMP)MnIII(OH)] (1) or 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinatomanganese(III) acetate [(TPFPP)MnIII(CH3COO)] (2)] occurred to yield 10-methyl-(9,10H)-acridone (Acr -O) in an oxygen-saturated benzonitrile (PhCN) solution under visible light irradiation. The photocatalytic reactivity of (P)MnIII in the presence of O2 is in proportion to concentrations of AcrH2 or O2 with the maximum turnover numbers of 17 and 6 for 1 and 2, respectively. The quantum yield with 1 was determined to be 0.14%. Deuterium kinetic isotope effects (KIEs) were observed with KIE = 22 for 1 and KIE = 6 for 2, indicating that hydrogen-atom transfer from AcrH2 is involved in the rate-determining step of the photocatalytic reaction. Femtosecond transient absorption measurements are consistent with photoexcitation of (P)MnIII, resulting in intersystem crossing from a tripquintet excited state to a tripseptet excited state. A mechanism is proposed where the tripseptet excited state reacts with O 2 to produce a putative (P)MnIV superoxo complex. Hydrogen-atom transfer from AcrH2 to (P)MnIV(O 2?-) generating a hydroperoxo complex (P)Mn IV(OOH) and AcrH? is likely the rate-determining step, in competition with back electron transfer to regenerate the ground state (P)MnIII and O2. The subsequent reductive O-O bond cleavage by AcrH? may occur rapidly inside of the reaction cage to produce (P)MnV(O) and AcrH(OH), followed by the oxidation of AcrH(OH) by (P)MnV(O) to yield Acr -O with regeneration of (P)Mn III.

Solvent Effects on Chemiluminescence from the Hydrogen Peroxide-Lucigenin Reaction: Kinetics of Light Emission in Mixed Polar Solvents

The effect of the reaction media composition on reaction kinetics was studied for the reaction of lucigenin (10,10'-dimethyl-9,9'-biacridinium nitrate) with hydrogen peroxide and alkali.Chemiluminescent emission as well as lucigenin disappearance were recorded in mixtures of water with the co-solvents methanol, ethanol, 1-propanol, dimethylsulfoxide, and dimethylformamide.The kinetic results (base and peroxide concentration influence on the reaction rate and the relative chemiluminescence yield) are very similar in all the reaction media, suggesting that the fundamental step in the disappearance of lucigenin and in light emission decay is HO2- addition to lucigenin.Lucigenin can also disappear through dark reactions with OH- or H2O2.The co-solvent acts as a catalyst for the reaction with HO2- and increases both the initial chemiluminescence intensity and the decay rate constant. Keywords.Chemiluminescence; Lucigenin; Solvent effects.

Formation of xanthone oxime and related compounds using a combination of tert-butyl nitrite and potassium hexamethyldisilazide

Synthesis of xanthone oxime and related compounds via nitrosation of the dibenzylic position using a combination of tert-butyl nitrite and potassium hexamethyldisilazide is described. The reaction conditions are effective for the synthesis of xanthone oxime as well as thioxanthone, acridone, and anthrone oximes, which have been difficult to synthesize from the corresponding ketones by conventional dehydrative condensation with hydroxylamine.