10-Methylacridin-9(10H)-one

Base Information

• Chemical Name: 10-Methylacridin-9(10H)-one
• CAS No.: 719-54-0
• Molecular Formula: C14H11 N O
• Molecular Weight: 209.247
• Hs Code.: 29339980
• European Community (EC) Number: 211-948-1
• NSC Number: 54142,1189
• DSSTox Substance ID: DTXSID50222159
• Nikkaji Number: J101.796I
• Wikidata: Q15632877
• Metabolomics Workbench ID: 45846
• ChEMBL ID: CHEMBL1288901
• Mol file: 719-54-0.mol

Synonyms:N-methylacridone

Chemical Property of 10-Methylacridin-9(10H)-one

Chemical Property:

• Appearance/Colour: LIGHT GREEN TO GREY-GREEN FINE CRYSTALLINE POWDER
• Vapor Pressure: 2.09E-05mmHg at 25°C
• Melting Point: 204-207 °C
• Refractive Index: 1.5780 (estimate)
• Boiling Point: 361.3°C at 760 mmHg
• PKA: -1.57±0.20(Predicted)
• Flash Point: 146.2°C
• PSA: 22.00000
• Density: 1.205g/cm³
• LogP: 2.69170
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 209.084063974
• Heavy Atom Count: 16
• Complexity: 263

Purity/Quality:

98% ^*data from raw suppliers

10-Methyl-9(10H)-acridinone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=O)C3=CC=CC=C31
• 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.

Technology Process of 10-Methylacridin-9(10H)-one

There total 201 articles about 10-Methylacridin-9(10H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

benzyldiisopropylamine (34636-09-4) + 10-methylacridinium perchlorate (26456-05-3) → 9,10-dihydro-10-methylacridine (4217-54-3) + 10-methyl-9, 10-dihydro-9-acridinone (719-54-0) + benzaldehyde (100-52-7) + 9-(Benzyl-isopropyl-amino)-10-methyl-acridinium; perchlorate

Guidance literature:

With oxygen; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1246/bcsj.65.55

Reference yield: 56.0%

10-methylacridinium perchlorate (26456-05-3) + N-Benzylpiperidine (2905-56-8) → 9,10-dihydro-10-methylacridine (4217-54-3) + 10-methyl-9, 10-dihydro-9-acridinone (719-54-0) + benzaldehyde (100-52-7) + 9-[Benzyl-(5-hydroxy-pentyl)-amino]-10-methyl-acridinium; perchlorate

Guidance literature:

With oxygen; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1246/bcsj.65.55

Reference yield: 55.0%

N,N-diethylbenzylamine (772-54-3) + 10-methylacridinium perchlorate (26456-05-3) → 9,10-dihydro-10-methylacridine (4217-54-3) + 10-methyl-9, 10-dihydro-9-acridinone (719-54-0) + benzaldehyde (100-52-7) + 9-(N-ethylbenzylamino)-10-methylacridinium perchlorate

Guidance literature:

With oxygen; In acetonitrile; for 24h; Product distribution; Mechanism; Ambient temperature; other tertiary amines; other time; also without air;

DOI:10.1246/bcsj.65.55

upstream raw materials:

acridine

dimethyl sulfate

9,10-dihydro-10-methylacridine

benzoic acid-(2,4,6,N-tetrachloro-anilide)

Downstream raw materials:

N-Methyl-9-chloracridinium

2,7-dibromo-10-methylacridine-9(10H)-one

9-(4-(dimethylamino)phenyl)-10-methyl-4a,9,9a,10-tetrahydroacridin-9-ol

10-methyl-N-phenylacridine-9(10H)-imine

Refernces

• 1、 Pereira, Ricardo C.,Pontinha, Ana Dora R.,Pineiro, Marta,Seixas de Melo, J. Sérgio. "A comprehensive spectral, photophysical and electrochemical study of synthetic water-soluble acridones. A new class of pH and polarity sensitive fluorescent probes". . p. 203 - 210. Retrieved 2019.
• 2、 Shinkai, Seiji,Ishikawa, Yu-ichi,Manabe, Osamu,Kunitake, Toyoki. "CHEMILUMINESCENCE OF 9-METHYLENEACRIDANS IN MICELLAR AND MEMBRANOUS SYSTEMS". . p. 1523 - 1526. Retrieved 1981.
• 3、 Shukla, Deepak,Rege, Francis de,Wan, Peter,Johnston, Linda J.. "Laser Flash Photolysis and Product Studies of the Photoionization of N-Methylacridan in Aqueous Solution". . p. 10240 - 10246. Retrieved 1991.
• 4、 Happ et al.. "-". . p. 3382,3383,3384,3387. Retrieved 1970.
• 5、 Varveri, Fannie S.,Mantaka-Marketou, Anastasia E.,Vassilopoulos, George,Nikokavouras, John. "Chemiluminescence in Model Membrane Structures. Chemiluminescence of Lucigenin in the Presence of Mg(OH)2 and Benzyl Alcohol. Temperature Effects". . p. 703 - 710. Retrieved 1988.
• 6、 Larena, Alicia,Urreaga, Joaquin Martinez. "Solvent Effects on Chemiluminescence from the Hydrogen Peroxide-Lucigenin Reaction: Kinetics of Light Emission in Mixed Polar Solvents". . p. 907 - 914. Retrieved 1991.
• 7、 Picot et al.. "-". . p. 3811. Retrieved 1977.
• 8、 Markovich,Kudryavtseva,Markovich,Koroleva. "Sulfonation of 10-carboxymethylene-9-acridanone under thermal and microwave conditions. Comparison of kinetic parameters". . . Retrieved 2013.
• 9、 Chi, Quan,Chen, Wanying,He, Zhike. "Mechanism of alcohol-enhanced lucigenin chemiluminescence in alkaline solution". . p. 990 - 995. Retrieved 2015.
• 10、 -. "Aromatic heterocycle substituted acridine quaternary ammonium salt derivative as well as preparation method and application thereof". . . Retrieved 2021/09/29.