104675-26-5

Basic information

• Product Name: 9-Amino-3,4-dihydroacridin-1(2H)-one
• Synonyms: 9-Amino-3,4-dihydroacridin-1(2H)-one;9-AMino-3,4-dihydro-2H-acridin-1-one;9-AMino-3,4-dihydro-1(2H)-acridinone
• CAS NO: 104675-26-5
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.24718
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates;Amines, Aromatics, Heterocycles, Intermediates
• Mol File: 104675-26-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 228-230°C
• Boiling Point: 467.2 °C at 760 mmHg
• Flash Point: 236.4 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 6.63E-09mmHg at 25°C
• Refractive Index: 1.708
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• CAS DataBase Reference: 9-Amino-3,4-dihydroacridin-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Amino-3,4-dihydroacridin-1(2H)-one(104675-26-5)
• EPA Substance Registry System: 9-Amino-3,4-dihydroacridin-1(2H)-one(104675-26-5)

Safety Data

• Hazardous Substances Data: 104675-26-5(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Intermediate in the preparation of Mentane.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1617, 1990 DOI: 10.1002/jhet.5570270617

InChI:InChI=1/C13H12N2O/c14-13-8-4-1-2-5-9(8)15-10-6-3-7-11(16)12(10)13/h1-2,4-5H,3,6-7H2,(H2,14,15)

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 35447-75-7 N-hydroxy-2-nitrobenzimidoyl chloride 
• 504-02-9 1,3-cylohexanedione 
• 144290-89-1 3-(2-nitrophenyl)-6,7-dihydrobenzo[d]isoxazol-4(5H)-one 
• 104675-23-2 N-(3-oxocyclohexen-1-yl)-2-aminobenzonitrile 
• 129578-50-3 4,5-dihydro-3H-isoxazolo<5,4,3-kl>acridine 
• 584-08-7 potassium carbonate 

Downstream Products

• 104628-12-8 9-[(Thiophen-2-ylmethyl)-amino]-3,4-dihydro-2H-acridin-1-one 
• 104586-88-1 9-[4,4-bis(3-fluorophenyl)butylamino]-3,4-dihydroacridin-1(2H)-one 
• 112964-98-4 velnacrine 
• 104586-70-1 3,4-Dihydro-9-(2-methylbenzylamino)acridin-1(2H)-one 
• 104675-45-8 3,4-dihydro-9-(4,4-diphenylbutylamino)acridin-1(2H)-one 
• 104586-94-9 9-[2-[Bis(4-fluorophenyl)methoxy]ethylamino]-3,4-dihydroacridin-1(2H)-one, maleate 
• 104586-81-4 9-(4-chlorobenzylamino)-3,4-dihydroacridin-1(2H)-one 

Relevant articles and documents

Synthesis and evaluation of 1,2,3,4-tetrahydro-1-acridone analogues as potential dual inhibitors for amyloid-beta and tau aggregation

Amyloid-β (Aβ) and tau protein are two crucial hallmarks in Alzheimer's disease (AD). Their aggregation forms are thought to be toxic to the neurons in the brain. A series of new 1,2,3,4-tetrahydro-1-acridone analogues were designed, synthesized, and evaluated as potential dual inhibitors for Aβ and tau aggregation. In vitro studies showed that compounds 25–30 (20 μM) with N-methylation of the quinolone ring effectively inhibited Aβ1-42 aggregation by 84.7%–99.5% and tau aggregation by 71.2%–101.8%. Their structure-activity relationships are discussed. In particular, 30 could permeate the blood-brain barrier, bind to Aβ1-42 and tau, inhibit Aβ1-42 β-sheets formation, and prevent tau aggregation in living cells.

Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles

A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 dust and HOAc using a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

Sulfuric acid-modified PEG-6000 (PEG-OSO3H): An efficient, bio-degradable and reusable polymeric catalyst for the solvent-free synthesis of poly-substituted quinolines under microwave irradiation

Sulfuric acid-modified polyethylene glycol 6000 (PEG-OSO3H) is applied as an efficient and eco-friendly polymeric catalyst for Friedlaender synthesis of poly-substituted quinolines from 2-aminoaryl ketones (or anthranilonitrile) and carbonyl compounds possessing a reactive methylene group under microwave irradiation and solvent-free conditions. The reactions are completed in short times, and the products are obtained in good to excellent yields. The Royal Society of Chemistry.