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
• Article Data: 124

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

Description

9(10H)-ACRIDONE, also known as acridanone, is a member of the acridine class of compounds, characterized by a 9,10-dihydroacridine structure with an oxo group substitution at position 9. It is a yellow crystalline powder and is recognized for its fluorescent properties.

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

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

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

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.

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.

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).

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.

Synthesis and biological evaluation of novel isoxazole derivatives from acridone

The present study was carried out in an?attempt to synthesize a new class of potential antibacterial agents. In this context, novel isoxazoles were synthesized and evaluated for their potential antibacterial behavior against four pathogenic bacterial strains. The synthesized compounds exhibited moderate-to-good antibacterial activity against these strains. The highest antibacterial activity was observed against the Escherichia coli strains, particularly for compounds 4a and 4e with phenyl and para-nitrophenyl groups on the isoxazole–acridone skeleton;?they showed promising minimum inhibitory concentration values of 16.88 and 19.01 μg/ml, respectively, compared with the standard drug chloramphenicol (22.41 μg/ml). The synthesized compounds were subjected to in silico docking studies to understand the mode of their interactions with the DNA topoisomerase complex (PDB ID: 3FV5) of E. coli. The molecular docking results showed that compounds 4a–l occupy the active site of DNA topoisomerase (PDB ID: 3FV5), stabilized via hydrogen bonding and hydrophobic interactions, which may be the reason behind their interesting in vitro antibacterial activity.