13161-85-8

Basic information

• Product Name: 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE
• Synonyms: 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE;1,2,3,4-TETRAHYDRO-9[10H]-ACRIDONE;1,2,3,4-TETRAHYDRO-9-ACRIDANONE;AKOS 222-12;1,2,3,4-Tetrahydro-910Hü-acridone, 98%;1,2,3,4-Tetrahydro-acridine-9(10H)-one;1,3,4,10-Tetrahydroacridin-9(2H)-one;9(2H)-Acridinone, 1,3,4,10-tetrahydro-
• CAS NO: 13161-85-8
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.25
• Mol File: 13161-85-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 350°Cat760mmHg
• Flash Point: 147.7°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 4.52E-05mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE(13161-85-8)
• EPA Substance Registry System: 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE(13161-85-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 13161-85-8(Hazardous Substances Data)

Usage

General Description

1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE is a chemical compound with the molecular formula C15H19NO. It is a bicyclic organic compound that is commonly used as a building block in the synthesis of pharmaceuticals and other organic compounds. It is known for its potential as a versatile intermediate in the production of various drugs and medical treatments. The compound has also been studied for its potential antimicrobial and antiviral properties. Additionally, it is used in the manufacture of dyes and pigments, as well as in organic synthesis as a reagent for various chemical reactions. Overall, 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE is a valuable and versatile chemical compound with a range of potential applications in pharmaceuticals, organic synthesis, and other industries.

InChI:InChI=1/C13H13NO/c15-13-9-5-1-3-7-11(9)14-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H,14,15)

Upstream product

• 38778-79-9 ethyl 2-(N-phenylamino)-1-cyclohexene-1-carboxylate 
• 3898-08-6 1,1-diphenylthiourea 
• 6833-04-1 N,N'-Diphenylpimelamide 
• 14807-16-0 9-Anilino-1,2,3,4-tetrahydroacridine 
• 2047-89-4 5,6,7,8,9,10-hexahydrocyclohept[b]indole 
• 62-53-3 aniline 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 96447-10-8 spiro<2H-3,1-benzoxazine-2,1'-cyclohexan>-4(1H)-one 
• 68-12-2 N,N-dimethyl-formamide 
• 104-94-9 4-methoxy-aniline 
• 108-94-1 cyclohexanone 
• 76854-95-0 2-amino-N,N-diethylbenzamide 
• 111232-49-6 1-(4-methoxybenzyl)spiro-4'-one 
• 28144-70-9 anthranilic acid amide 

Downstream Products

• 5396-30-5 9-chloro-1,2,3,4-tetrahydroacridine 
• 443662-39-3 7-bromo-1,2,3,4-tetrahydro-acridin-9-ol 
• 578-95-0 10H-acridin-9-one 
• 56717-04-5 1,2,3,4-tetrahydroacridin-9-ol 
• 260-94-6 acridine 
• 111232-55-4 N-<4-<(1,2,3,4-tetrahydro-9-acridinyl)amino>-3-methoxyphenyl>methanesulfonamide 
• 5782-90-1 9-(1-piperidinyl)-1,2,3,4-tetrahydroacridine 
• 79000-43-4 9-phenoxy-1,2,3,4-tetrahydro-acridine 
• 321-64-2 tacrin 
• 53618-67-0 6-Brom-4-chlor-2,3-tetramethylenchinolin 
• 7032-37-3 4-Morpholino-2,3-tetramethylenequinoline 

Relevant articles and documents

Visible-Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N-Diacyliminium Ions

Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido- and perhydroazepino[1,2-a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon C,N-diacyliminium ions and can be functionalized with the aid of phosphoric acid organocatalysis.

Synthesis of certain tetrahydroacridine derivatives of anticipated medicinal value

This study aims at the synthesis and evaluation of the chemotherapeutic activity of a number of 9-substituted tetrahydroacridine derivatives. The starting material, acridine hydrazide, could be prepared through the interaction between cyclohexanone and anthranilic acid, then chlorination of the product, then condensation of the last compound with hydrazine hydrate. The structures of the new compounds were established by IR, 1H NMR, MS spectra, and elemental analysis in certain cases. Antitumor activities as a trial to obtain more effective and less toxic agents were evaluated. The antitumor activity results indicated that the selected tetrahydroacridine derivatives showed antitumor activity against the liver cancer (HEPG2) tumor cell line tested, but with varying intensities in comparison to the known anticancer drugs, 5-fluorouracil and doxorubicin. It was found that compound VIb was the most active and induced a marked growth inhibition (0.694 μg/ml concentration) in a dose-dependent manner against liver cancer (HEPG2), while compound XVIIIa was second in regards to the growth inhibition activity (2.97 μg/ml concentration).

The Vilsmeier-Haack formylation of 2,3-dihydro-4H-1,3-benzoxazin-4-ones and isomeric 1,2-dihydro-4H-3,1-benzoxazin-4-ones: An effective approach to functionalized 2H-/4H-chromenes and tetrahydroacridines

We found that 1,3- and isomeric 3,1-benzoxazin-4-ones react with the Vilsmeier reagent in vastly different ways. Thus, either 2H- or 4H-chromenes were obtained in good yields when 1,3-benzoxazin-4-ones were reacted at 75-80 °C, while the formylation of 3,1-benzoxazines at ambient temperature leads to acridine-9-one or 9-chloroacridine derivatives, depending on the amount of Vilsmeier reagent and the nature of substrate.