578-95-0

Basic information

• Product Name: 9(10H)-ACRIDONE
• Synonyms: 9-Acridone;Acridanone;Acridin-9-one;Acridine, 9,10-dihydro-9-oxo-;Dihydroketoacridine;10H-ACRIDIN-9-ONE;AKOS 215-92;ACRIDON
• CAS NO: 578-95-0
• Molecular Formula: C₁₃H₉NO
• Molecular Weight: 195.22
• EINECS: 209-434-7
• Product Categories: Heterocycles;Piperazine derivates;Aromatics;Fluorescent Labels & Indicators;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 578-95-0.mol

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 331.88°C (rough estimate)
• Flash Point: 155.049 °C
• Appearance: Yellow/Crystalline Powder
• Density: 1.1266 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6060 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• PKA: -0.30±0.30(Predicted)
• Water Solubility: Insoluble in benzene, chloroform, ether, water and ethanol.
• BRN: 7104
• CAS DataBase Reference: 9(10H)-ACRIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: 9(10H)-ACRIDONE(578-95-0)
• EPA Substance Registry System: 9(10H)-ACRIDONE(578-95-0)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22-40
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• RTECS: AR6976000
• TSCA: Yes
• Hazardous Substances Data: 578-95-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9(10H)-ACRIDONE is used as a fluorescent tag for antibody catalysis, taking advantage of its inherent fluorescent properties to enhance the detection and analysis of specific antibodies in various research and diagnostic applications.
Used in Chemical Industry:
9(10H)-ACRIDONE is used in the preparation of methyl 9,10-dihydro-9-oxoacridine-10-pentanoate, which serves as an important intermediate in the synthesis of various organic materials, particularly in the dyeing process.
Used in Textile Industry:
9(10H)-ACRIDONE, through its derivative methyl 9,10-dihydro-9-oxoacridine-10-pentanoate, is utilized for dyeing organic materials, contributing to the development of vibrant and long-lasting colors in textiles and other related products.

Purification Methods

Dissolve ~1g in ca 1% NaOH (100mL), add 3M HCl to pH 4 when acridone separates as a pale yellow solid with m just above 350o (sharp). It can be recrystallised from large volumes of H2O to give a few mg. It is soluble in 160 parts of boiling EtOH (540 parts at 22o) [Albert & Phillips J Chem Soc 1294 1956]. Afew decigms are best crystallised as the hydrochloride from 400 parts of 10N HCl (90% recovery) from which the free base is obtained by washing the salt with H2O. A small quantity can be recrystallised (as the neutral species) from boiling AcOH. Larger quantities are best recrystallised from a mixture of 5 parts of freshly distilled aniline and 12.5 parts of glacial acetic acid. Acridone distils unchanged at atmospheric pressure, but the boiling point was not recorded, and some sublimation occurs below 350o. It has UV: 399nm. [see max Albert, The Acridines Arnold Press pp 201, 372 1966; for pKa see Kalatzis J Chem Soc (B) 96 1969, Beilstein 23/9 V 7.]

InChI:InChI=1/C13H9NO/c15-13-9-5-1-3-7-11(9)14-12-8-4-2-6-10(12)13/h1-8H,(H,14,15)

Upstream product

• 123-91-1 1,4-dioxane 
• 16355-92-3 1,10-diiododecane 
• 23043-52-9 N-(acridin-9-yl)acetamide 
• 87-17-2 salicylanilide 
• 260-94-6 acridine 
• 1207-69-8 9-Chloroacridine 
• 141-43-5 ethanolamine 
• 6540-78-9 acridine-9-thione 
• 74-88-4 methyl iodide 
• 91-40-7 2-(phenylamino)benzoic acid 
• 56717-04-5 4-hydroxy-2,3-(tetramethylene)quinoline 
• 13161-85-8 1,2,3,4,9,10-hexahydroacridin-9-one 
• 88-21-1 2-amino-1-benzenesulfonic acid 
• 10228-90-7 9-methoxyacridine 

Downstream Products

• 60536-19-8 N-butylacridone 
• 611-64-3 9-methyl-acridine 
• 6267-02-3 9,9‐dimethyl‐10H‐acridine 
• 26862-43-1 4-acridin-9-yl-N,N-dibenzyl-aniline 
• 35586-79-9 4-acridin-9-yl-3,N,N-trimethyl-aniline 
• 92-81-9 acridine 
• 60536-17-6 N(-n-propyl)acridine-9-one 
• 3785-45-3 10-(2-dimethylamino-propyl)-10H-acridin-9-one 
• 35586-78-8 4-acridin-9-yl-2,N,N-trimethyl-aniline 
• 35586-84-6 4-acridin-9-yl-2-methoxy-N,N-dimethyl-aniline 
• 60536-22-3 10-diethylaminoethyl-9-acridinone 
• 260-94-6 acridine 
• 24275-68-1 9-(4-dimethylaminophenyl)acridine 
• 6266-90-6 9-(4-diethylaminophenyl)acridine 

Relevant articles and documents

5-(Acridin-9-ylamino)uracil-A hydrolytically labile nucleobase modification in peptide nucleic acid

5-Aminouracil (5-AU) is a readily available yet underutilized starting material for the synthesis of labelled nucleobase analogues. We have prepared the derivative of 5-AU with the amine-reactive chromophore 9-chloroacridine for the purpose of investigating its potential as a base-discriminating fluorophore. 9-Chloroacridine readily undergoes substitution by reaction with 5-AU to yield a fluorescent nucleobase that after standard manipulations produced a monomer suitable for incorporation into peptide nucleic acid (PNA) by fluorenylmethyloxycarbonyl (Fmoc)-based oligomerization chemistry. Although the monomer was stable in organic solvents, once incorporated into an oligomer the 5-substitution was found to be thermally labile and hydrolyzed to a small degree in neutral aqueous solution during study of its hybridization to cDNA. We have determined that 5-(acridin-9-ylamino)uracil and related derivatives produce the highly fluorescent acridone and 5-AU by hydrolysis in water.

Generation of 9(10H)-acridone from anthranilic acid

Diazotization of anthranilic acid with butyl nitrite in refluxing THF gave rise to acridone.

BASE-INDUCED OXYGENATION AND CHEMILUMINESCENCE OF 10-METHYLACRIDINIUM AND 1-METHYLQUINOLINIUM SALTS IN DIMETHYL SULFOXIDE.

10-Methylacridinium methyl sulfate and the 1-methylquinolinium salt gave strong light emission, when oxidized with ground state oxygen in the presence of t-BuOK in DMSO, owing to the fluorescence of 10-methyl-9(10H)-acridinone and 1-methyl-1(4H)-quinolinone excited to their S//1 state.

Targeting tyrosine kinase: Development of acridone – pyrrole – oxindole hybrids against human breast cancer

Based on the molecular modelling studies, a rational modification of the lead molecule was made to develop highly potent compounds showing anti-cancer activity against human breast cancer cell lines MCF 7, MDA-MB-468 and T-47D. The most potent compounds have Log P and total polar surface area 4.4–5.4 and 59.8 ? respectively and they also exhibited promising ADME profile.

Intramolecular cyclization of N-phenylanthranilic acid catalyzed by MCM-41 with different pore diameters

Micro-mesoporous sieves MCM-41 with different pore diameters were synthesized under microwave irradiation, characterized by X-ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, N2 adsorption- desorption and temperature-programmed desorption of NH3 (NH3-TPD). Intramolecular cyclization of N-Phenylanthranilic acid to acridone catalyzed by MCM-41 with different pore diameters was investigated. The results indicate that the yields increased significantly with the decrease of pore diameter of MCM-41. Furthermore, the yield of acridone under microwave irradiation was higher than that under conventional heating.

Reduction of Acridine and 9-Chloroacridine with Red Phosphorus in the KOH/DMSO System

Abstract: Acridine reacts with red phosphorus in the KOH/DMSO(H2O) system on heating (100°C, 3 h) to give 9,10-dihydroacridine regioselectively in quantitative yield. Under similar conditions, 9-chloroacridine reacts with Pred/KOH/DMSO(H2O) system to afford 9,10-dihydroacridine and acridone in 51 and 40% yield, respectively.

Synthesis, spectroscopic characterization (FT-IR, NMR) and DFT computational studies of new isoxazoline derived from acridone

In this study, a new isoxazoline derived from acridone, 10‐{[3‐(4‐chlorophenyl)‐4,5‐dihydro‐1,2‐oxazol‐5 yl]methyl} acridone (3) was successfully synthesized and characterized by FT-IR, 1H NMR, 13C NMR and HRMS. The preparation of compound (3) was achieved by 1,3-dipolar cycloaddition reaction between 4?chloro-N-hydroxybenzimidoyl chloride and 10-allylacridone using environment friendly methods. In an effort to complete the chemical structure description of the synthetized compound, Density Functional Theory (DFT) was applied using Gaussian09 and Gaussian view5 programs. The theoretical calculations were used as a compliment to the experimental studies. The computing of geometric parameters, optimization energies, frontier molecular orbital energies, Molecular surface electrostatic potential (MESP) and Mulliken charges were calculated using DFT/B3LYP method with 6–31G(d,p) as basis set. The Infrared vibrational frequencies and 1H and 13C NMR chemical shifts were also calculated and their scaled values are in agreement with the experimental results.

Novel highly selective and sensitive fluorescent sensor for copper detection based on N-acylhydrazone acridone derivative

A new N-acylhydrazone based on acridone (S1) was synthesized by Schiff base condensation of 2-(9-oxoacridin-10-yl)acetohydrazide and salicylaldehyde and studied as selective fluorescence turn-off sensing towards Cu2+ ions in aqueous media. S1 demonstrated fluorescence turn-off sensing towards Cu2+ ions. Conversely, the metal ions K+, Mg2+, Zn2+, Fe2+, Al3+, Pb2+, Cr2+, Cd2+, Ag+, Fe3+, Ba2+, Hg2+, Mn2+, Co2+, and Ni2+ produced only minor decrease in the fluorescence of the system. The binding ratio of S1–Cu2+ complex was determined from the Job plot to be 1:2. Moreover, the S1–Cu2+ complex showed good fluorescence turn-off in presence of different counter ions of copper. In addition, the detection limit of S1 towards Cu2+ ions is 0.80 μM, which is enough for sensing the Cu2+ in the biological system and water within the U.S Environmental Protection Agency limit (～20 μM).

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.

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.