1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE

Base Information

• Chemical Name: 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE
• CAS No.: 13161-85-8
• Molecular Formula: C13 H13 N O
• Molecular Weight: 199.252
• Hs Code.: 2933990090
• Mol file: 13161-85-8.mol

Synonyms:9-Acridanone, 1,2,3,4-tetrahydro-(7CI,8CI); 1,2,3,4-Tetrahydro-9(10H)-acridone; 1,2,3,4-Tetrahydroacridone;1,3,4,10-Tetrahydro-9(2H)-acridinone; NSC 46875

Chemical Property of 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE

Chemical Property:

• Vapor Pressure: 4.52E-05mmHg at 25°C
• Boiling Point: 350°Cat760mmHg
• Flash Point: 147.7°C
• PSA: 32.86000
• Density: 1.2g/cm³
• LogP: 2.40690

Purity/Quality:

95% ^*data from raw suppliers

1,2,3,4-Tetrahydro-9-acridanone 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE, also known by various synonyms such as 1,2,3,4-Tetrahydroacridone, is a tetrahydroacridine derivative with potential medicinal applications. It serves as a key intermediate in the synthesis of nitrogen-containing heterocycles, including antitumor agents. Studies indicate that certain tetrahydroacridine derivatives exhibit notable anticancer activity, particularly against liver cancer (HEPG2), with some compounds demonstrating dose-dependent growth inhibition. Additionally, this scaffold has been explored in the development of heterodimers targeting topoisomerases, showing selective cytotoxicity toward cancer cells while sparing normal fibroblasts. Its synthesis often involves condensation reactions, such as the Vilsmeier-Haack formylation, to yield functionalized acridine derivatives.

Technology Process of 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE

There total 29 articles about 1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

spiro<2H-3,1-benzoxazine-2,1'-cyclohexan>-4(1H)-one (96447-10-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 1,2,3,4,9,10-hexahydroacridin-9-one (13161-85-8)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; Cooling with ice;

spiro<2H-3,1-benzoxazine-2,1'-cyclohexan>-4(1H)-one; for 0.5h;

DOI:10.1016/j.tet.2015.06.069

Reference yield: 90.0%

10-(4-methoxybenzyl)-1,2,3,4,9,10-hexahydroacridin-9-one (111232-51-0) → 1,2,3,4,9,10-hexahydroacridin-9-one (13161-85-8)

Guidance literature:

With hydrogenchloride; for 1h; Heating;

DOI:10.3987/R-1987-01-0191

Reference yield: 89.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + 2-carbomethoxyaniline (134-20-3) → 1,2,3,4,9,10-hexahydroacridin-9-one (13161-85-8)

Guidance literature:

In water; toluene; at 120 ℃; for 5h;

upstream raw materials:

9-Anilino-1,2,3,4-tetrahydroacridine

ethyl 2-(N-phenylamino)-1-cyclohexene-1-carboxylate

cyclohexanone

anthranilic acid

Downstream raw materials:

acridine

tacrin

6-Brom-4-chlor-2,3-tetramethylenchinolin

4-Morpholino-2,3-tetramethylenequinoline