6269-27-8

Basic information

• Product Name: 3-Chloro-9(10H)-acridinone
• Synonyms: 3-Chloro-9(10H)-acridinone
• CAS NO: 6269-27-8
• Molecular Formula: C₁₃H₈ClNO
• Molecular Weight: 229.66
• Mol File: 6269-27-8.mol

Chemical Properties

• Boiling Point: 390.6°C at 760 mmHg
• Flash Point: 190°C
• Appearance: /
• Density: 1.346g/cm³
• Vapor Pressure: 2.63E-06mmHg at 25°C
• Refractive Index: 1.649
• CAS DataBase Reference: 3-Chloro-9(10H)-acridinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-9(10H)-acridinone(6269-27-8)
• EPA Substance Registry System: 3-Chloro-9(10H)-acridinone(6269-27-8)

Safety Data

• Hazardous Substances Data: 6269-27-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H8ClNO/c14-8-5-6-10-12(7-8)15-11-4-2-1-3-9(11)13(10)16/h1-7H,(H,15,16)

Upstream product

• 59304-30-2 6-chloroacridine 
• 38046-68-3 3-(4-chlorophenyl)benzo[c]isoxazole 
• 50433-64-2 3-amino-10H-acridin-9-one 
• 35547-70-7 3,9-dichloroacridine 
• 108-90-7 chlorobenzene 
• 552-89-6 2-nitro-benzaldehyde 
• 13278-36-9 N-(3-chlorophenyl)anthranilic acid 
• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 
• 71-43-2 benzene 
• 19218-88-3 N-phenyl-4-chloroanthranilic acid 
• 50-84-0 2,4 dichlorobenzoic acid 
• 62-53-3 aniline 
• 108-42-9 3-chloro-aniline 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 59304-30-2 6-chloroacridine 
• 35547-70-7 3,9-dichloroacridine 
• 270088-53-4 3-Chloro-9-(4-nitro-phenylsulfanyl)-acridine 
• 3407-98-5 5-Amino-2-chloroacridin 
• 70974-00-4 10-benzyl-3-chloroacridin-9(10H)-one 

Relevant articles and documents

Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids

An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.

Synthesis method of acridone derivative

The application relates to a synthesis method of an acridone derivative. The synthesis method comprises the following steps: mixing a compound shown in a formula (I), a photocatalyst and a solvent, reacting under the conditions of oxygen and lighting and obtaining the acridone derivative. The synthesis method of the acridone derivative has the beneficial effects that the photocatalyst can catalyzethe compound shown in the formula (I) to carry out intramolecular hydrocarbon ammoniation reaction under the conditions of oxygen and lighting so as to synthesize the acridone derivative, and the pretreatment for the compound shown in the formula (I) is not needed; the operation is simple and convenient, and the condition is mild, the yield is high; the synthesis method conforms to the economic and environment-friendly characteristics of atoms and has high practical value for industrial preparation of the acridone derivative.

Pd-NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3-aroylquinolin-4 (1H)-one and acridone scaffolds

We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd- NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like-COMe, -COOMe, -F, -Cl, -Br, -NH2, -CN) are well tolerated in this reaction. In addition, we have also demonstrated a new efficient route for the synthesis of biologically active and pharmaceutically important 2-substituted 3-Aroylquinolin-4(1H)-ones and acridone scaffolds.

Transition-Metal-Free Synthesis of Acridones via Base-Mediated Intramolecular Oxidative C?H Amination

Intramolecular oxidative C?H amination of 2-aminobenzophenones was achieved in the presence of potassium tert-butoxide and dimethyl sulfoxide. A series of functionalized acridones were prepared in moderate to excellent yields in a mild, efficient, and transition-metal-free manner. (Figure presented.).

Tandem arylation/friedel-crafts reactions of o-acylanilines with diaryliodonium salts: A modular synthesis of acridine derivatives

A modular method to synthesize acridine derivatives was developed with o-acylanilines and diaryliodonium salts. The reactions proceeded smoothly under Cu-catalyzed or metal-free reaction conditions at elevated temperature through tandem arylation/Friedel-Crafts reactions.

Synthesis of novel heme-interacting acridone derivatives to prevent free heme-mediated protein oxidation and degradation

Heme is an important prosthetic molecule for various hemoproteins and serves important function in living aerobic organisms. But degradation of hemoprotein, for example, hemoglobin during different pathological conditions leads to the release of heme, which is very toxic as it induces oxidative stress and inflammation due to its pro-oxidant nature. Thus, synthesis of compound that will detoxify free heme by interacting with it would be fruitful for the management of heme-induced pathogenesis. Here, we report the synthesis of a novel natural product arborinine and some other acridone derivatives, which interact with free heme. These acridones in vitro block heme-mediated protein oxidation and degradation, markers for heme-induced oxidative stress.

Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition

Novel 10-{[3-(6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)- 4,5-dihydro-5-isoxazolyl]methyl}-9(10H)-acridinone derivatives (13-16) were synthesized by 1,3-dipolar cycloaddition using the carbohydrate derivative as dipole and different 10-allyl-9(10H)-acridinone derivatives (9-12) as dipolarophiles. The new cycloadducts as well as the dipolarophiles precursors were characterized spectroscopically. Copyright Taylor & Francis Group, LLC.

Inhibition of Cryptosporidium parvum in vitro by 9-(alkylthio)acridine derivatives

The synthesis of several acridinic thioethers is described. Compounds prepared were tested in vitro as potential drugs against the opportunistic infection known as cryptosporidiosis. With a view to predict activity, the quantitative structure-activity relationships were investigated. Correlations between experimental data and either log P or pKa are discussed.

Structure-trypanodical activity relationships

A set of 9-thioalkylacridinones, has been prepared and investigated' in vitro' against T. cruzi. Structure-antiparasitic activity relationships are detailed with a view to identify the major structural parameters for the activity under consideration.