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

Chemical Properties

YELLOW CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 578-95-0 differently. You can refer to the following data:
1. 9(10H)-Acridone is a catabolic product of carbamazepine (C175840) metabolite and can be used as a fluorescent tag for antibody catalysis.
2. 9(10H)-Acridone is used in the preparation of methyl 9,10-dihydro-9-oxoacridine-10-pentanoate, use for dyeing the organic materials.
3. 9(10H)-Acridanone (acridone) was used in the preparation of methyl 9,10-dihydro-9-oxoacridine-10-pentanoate.

Definition

ChEBI: A member of the class of acridines that is 9,10-dihydroacridine substituted by an oxo group at position 9.

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

• 260-94-6 acridine 
• 1207-69-8 9-Chloroacridine 
• 141-43-5 ethanolamine 
• 6540-78-9 acridine-9-thione 
• 74-88-4 methyl iodide 
• 56717-04-5 4-hydroxy-2,3-(tetramethylene)quinoline 
• 88-21-1 2-amino-1-benzenesulfonic acid 
• 10228-90-7 9-methoxyacridine 
• 73302-63-3 9-ethoxyacridine 
• 606-10-0 2,2'-diaminobenzophenone 
• 64-17-5 ethanol 
• 6705-07-3 10H-acridine-9-selone 
• 67-64-1 acetone 
• 552-89-6 2-nitro-benzaldehyde 

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).

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.

Novel series of N-acylhydrazone based on acridone: Synthesis, conformational and theoretical studies

In this work, novel N-acylhydrazone derivatives from acridone have been synthesized by condensation of 9-oxoacridin-10(9H)-yl)acetohydrazide with various aldehyde and ketone. The structures of these novel compounds were elucidated by 1H NMR, 13C NMR, IR and mass spectroscopy. The NMR data shows two conformations (E, trans and E, cis) due to N–C(O) bond rotation, the conformations of synthesized compounds have been investigated by different NMR methods. The rotational barriers around N–C(O) bond for compound 5a was measured in DMSO using dynamic NMR spectroscopy, this result was confirmed by DFT calculations at B3LYP/6–31 G (d) level in DMSO.