Acridone

Base Information

• Chemical Name: Acridone
• CAS No.: 578-95-0
• Deprecated CAS: 790240-54-9
• Molecular Formula: C13H9NO
• Molecular Weight: 195.221
• Hs Code.: 29339900
• European Community (EC) Number: 209-434-7
• NSC Number: 408196,7664,138672
• UNII: 6BK306GUQA
• DSSTox Substance ID: DTXSID8060371
• Nikkaji Number: J1.702.427B,J1.738.871A,J66.880J
• Wikipedia: Acridone
• Wikidata: Q342721
• Metabolomics Workbench ID: 57536
• ChEMBL ID: CHEMBL436589
• Mol file: 578-95-0.mol

Synonyms:9(10H)-acridone;9-azaanthracen-10-one;acridone

Chemical Property of Acridone

Chemical Property:

• Appearance/Colour: Yellow crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.642
• Boiling Point: 355.004 °C at 760 mmHg
• PKA: -0.30±0.30(Predicted)
• Flash Point: 155.049 °C
• PSA: 32.86000
• Density: 1.231 g/cm³
• LogP: 2.68130
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in benzene, chloroform, ether, water and ethanol.
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 195.068413911
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98% min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22-40
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Acridine Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3N2
• Uses: 9(10H)-Acridone is a catabolic product of carbamazepine (C175840) metabolite and can be used as a fluorescent tag for antibody catalysis. 9(10H)-Acridone is used in the preparation of methyl 9,10-dihydro-9-oxoacridine-10-pentanoate, use for dyeing the organic materials. 9(10H)-Acridanone (acridone) was used in the preparation of methyl 9,10-dihydro-9-oxoacridine-10-pentanoate.

Technology Process of Acridone

There total 172 articles about Acridone 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: 99.0%

2-(phenylamino)benzoic acid (91-40-7) → 10H-acridin-9-one (578-95-0,790240-54-9)

Guidance literature:

With polyphosphoric acid; at 120 ℃; for 3.5h;

DOI:10.1002/ejoc.201800257

Reference yield: 99.0%

acridine (92-81-9) → 10H-acridin-9-one (578-95-0,790240-54-9)

Guidance literature:

With tert.-butylhydroperoxide; 0.5C₃₄H₁₈N₁₆^(4-)*2H₂O*2Cu⁽¹⁺⁾*C₃H₇NO; In water; at 20 ℃; for 4h; Reagent/catalyst; Sonication;

DOI:10.1021/acs.cgd.8b01527

Reference yield: 94.0%

1-phenyl-indole-2,3-dione (723-89-7) → 10H-acridin-9-one (578-95-0,790240-54-9)

Guidance literature:

With pyridine; oxygen; copper(II) nitrate; In dimethyl sulfoxide; at 130 ℃; for 24h; under 760.051 Torr;

DOI:10.1021/acs.orglett.8b00957

upstream raw materials:

1,4-dioxane

1,10-diiododecane

N-(acridin-9-yl)acetamide

salicylanilide

Downstream raw materials:

N-butylacridone

9-methyl-acridine

9,9‐dimethyl‐10H‐acridine

4-acridin-9-yl-N,N-dibenzyl-aniline

Refernces

• 1、 Matarazzo, Augusto,Moustafa, Mohamed E.,Hudson, Robert H.E.. "5-(Acridin-9-ylamino)uracil-A hydrolytically labile nucleobase modification in peptide nucleic acid". . p. 1202 - 1206. Retrieved 2013.
• 2、 Suzuki,Kazui,Tsukamoto,Kato,Izawa. "BASE-INDUCED OXYGENATION AND CHEMILUMINESCENCE OF 10-METHYLACRIDINIUM AND 1-METHYLQUINOLINIUM SALTS IN DIMETHYL SULFOXIDE.". . p. 1519 - 1521. Retrieved 1983.
• 3、 Xiao, Shangyou,Xu, Guang,Chen, Gang,Mu, Xiaojing,Chen, Zhitao,Zhu, Jun,He, Yi. "Intramolecular cyclization of N-phenylanthranilic acid catalyzed by MCM-41 with different pore diameters". . p. 10125 - 10135. Retrieved 2015.
• 4、 Aarjane, Mohammed,Slassi, Siham,Ghaleb, Adib,Amine, Amina. "Synthesis, spectroscopic characterization (FT-IR, NMR) and DFT computational studies of new isoxazoline derived from acridone". . . Retrieved 2021.
• 5、 -. "Preparation method of acridone". Paragraph 0020-0033. . Retrieved 2021/09/26.
• 6、 -. "Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products". Paragraph 0069-0071. . Retrieved 2021/07/17.