719-54-0

Basic information

• Product Name: 10-METHYL-9(10H)-ACRIDONE
• Synonyms: 10-Methyl-9-acridanone;10-Methylacridon;9(10H)-Acridinone, 10-methyl-;9-Acridanone, 10-methyl-;10-METHYL-9(10H)-ACRIDINONE;10-METHYL-9(10H)-ACRIDONE;AURORA KA-3718;LABOTEST-BB LT00068579
• CAS NO: 719-54-0
• Molecular Formula: C₁₄H₁₁NO
• Molecular Weight: 209.24
• EINECS: 211-948-1
• Product Categories: Miscellaneous;Functional Materials;Photopolymerization Initiators
• Mol File: 719-54-0.mol
• Article Data: 105

Chemical Properties

• Melting Point: 204-207 °C
• Boiling Point: 348.61°C (rough estimate)
• Flash Point: 146.2°C
• Appearance: /
• Density: 1.0966 (rough estimate)
• Vapor Pressure: 2.09E-05mmHg at 25°C
• Refractive Index: 1.5780 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Methanol (Slightly)
• PKA: -1.57±0.20(Predicted)
• CAS DataBase Reference: 10-METHYL-9(10H)-ACRIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: 10-METHYL-9(10H)-ACRIDONE(719-54-0)
• EPA Substance Registry System: 10-METHYL-9(10H)-ACRIDONE(719-54-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 719-54-0(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT GREEN TO GREY-GREEN FINE CRYSTALLINE POWDER

Uses

10-Methyl-9(10H)-acridinone is an intermediate in the synthesis of 9-Mesityl-10-methylacridinium Tetrafluoroborate (M258620). 9-Mesityl-10-methylacridinium Tetrafluoroborate can be used for the synthesis of?γ-butyrolactones, γ-lactams and pyrrolidines and also it has been reported by Nicewicz et al. to mediate myriad transformations through Photoredox Catalysis. The applications include the anti-Markovnikov hydroamination of alkenes and 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

• 260-94-6 acridine 
• 77-78-1 dimethyl sulfate 
• 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 
• 2148-14-3 9-phenoxyacridine 
• 80-48-8 methyl p-toluene sulfonate 
• 85137-67-3 2-(10-methyl-9,10-dihydro-acridin-9-yl)-1-phenyl-ethanone 
• 66762-83-2 C₂₁H₁₇NO₂ 
• 541-98-0 6-methyl-pyran-2,4-dione 
• 95256-36-3 9,9'-oxy-bis(10-methylacridinium)bis(trifluoromethanesulfonate) 
• 73646-75-0 C₁₅H₁₃NO₂ 

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 
• 74975-62-5 9-diphenylene-10-methylacridan 
• 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 
• 674783-97-2 9?mesityl-10-methylacridinium perchlorate 

Relevant articles and documents

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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.

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.

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.

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.

Origin of Chemiluminescence Accompanying the Reaction of the 9-Cyano-10-methylacridinium Cation with Hydrogen Peroxide

The 9-cyano-10-methylacridinium cation possesses an electrophilic center at the carbon atom in position (9) susceptible to the addition of anions. The addition of OOH- to this cation-in weakly acidic, neutral, or alkaline media-initiates processes leading to the formation of electronically excited 10-methyl-9-acridinone, which deactivates by light emission. The effect of changes in reactant concentrations and pH on emission decay with time, as well as other features of the accompanying chemiluminescence, were established. Calculations carried out at the semiempirical and density functional theory level demonstrated that initial addition of OOH- and subsequent processes lead either to the elimination of OCNH (in weakly acidic and neutral media) or OCN- (in alkaline media) and that their exothermicity is sufficiently high to generate electronically excited 10-methyl-9-acridinone. On the other hand, primary addition of OH- to C(9) in alkaline media initiates the conversion of the cation to the nonexcited 10-methyl-9-acridinone. This relatively rapid process influences to a substantial extent the intensity of the chemiluminescence. The prospects for the analytical application of 9-cyano-10-methylacridinium salts are briefly outlined.

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Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters

A MsOH-catalyzed oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.

Aromatic heterocycle substituted acridine quaternary ammonium salt derivative as well as preparation method and application thereof

The invention belongs to the technical field of pharmaceutical compounds, relates to an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative and a preparation method and application thereof, and has the structure shown in a formula (I). In-flight R1 A compound selected from the group consisting of aryl and heteroaryl. Substituted aryls. X Is a halogen or benzenesulfonate anion. The invention provides an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative as well as a preparation method and application thereof, and is designed to synthesize an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative through a simplified structure, and is designed to synthesize an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative so as to achieve the unique antibacterial effect by inhibiting the bacteria FtsZ and bacterial biofilm.