70401-28-4

Basic information

• Product Name: 2,9-DIMETHYLACRIDINE
• Synonyms: 2,9-DIMETHYLACRIDINE
• CAS NO: 70401-28-4
• Molecular Formula: C₁₅H₁₃N
• Molecular Weight: 207.27
• Mol File: 70401-28-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 374.831°C at 760 mmHg
• Flash Point: 164.936°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.684
• CAS DataBase Reference: 2,9-DIMETHYLACRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,9-DIMETHYLACRIDINE(70401-28-4)
• EPA Substance Registry System: 2,9-DIMETHYLACRIDINE(70401-28-4)

Safety Data

• Hazardous Substances Data: 70401-28-4(Hazardous Substances Data)

Usage

Type of compound

Polycyclic aromatic hydrocarbon

Usage

Dye intermediate, pharmaceutical production

Color

Yellow to orange solid

Odor

Strong

Solubility

Soluble in organic solvents, insoluble in water

Hazards

Mutagenic and carcinogenic properties, should be handled with caution

Synthesis use

Starting material for dyes, pigments, and specialty chemicals.

InChI:InChI=1/C15H13N/c1-10-7-8-15-13(9-10)11(2)12-5-3-4-6-14(12)16-15/h3-9H,1-2H3

Upstream product

• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 
• 551-93-9 2-aminoacetophenone 
• 5720-05-8 4-methylphenylboronic acid 
• 17933-03-8 m-tolylboronic acid 
• 60956-23-2 3,4-dibromotoluene 
• 1433772-22-5 N'-(1-(2-aminophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 1246225-50-2 2-chloro-4-methyl-N-(2-vinylphenyl)aniline 
• 620-84-8 4-methyldiphenylamine 
• 64-19-7 acetic acid 
• 106-38-7 para-bromotoluene 
• 589-92-4 1-methylcyclohexan-4-one 
• 1431475-35-2 (E)-N-phenyl-1-(tol-3-yl)ethan-1-imine 
• 622-37-7 Phenyl azide 

Downstream Products

• 101298-11-7 N',N'-dimethyl-N-(2-methyl-acridin-9-ylmethylene)-p-phenylenediamine-N-oxide 
• 70401-29-5 2-methylacridine-10-carboxaldehyde 

Relevant articles and documents

Tert-Butyl Bromide-Promoted Intramolecular Cyclization of 2-Arylamino Phenyl Ketones and Its Combination with Cu-Catalyzed C-N Coupling: Synthesis of Acridines at Room Temperature

Herein, a facile intramolecular cyclization of 2-arylamino phenyl ketones is established to supersede the traditional high-temperature, strongly acidic conditions and achieve 9-substituted acridines, by virtue of the combination of 2,2,2-trifluoroethanol and tert-butyl bromide. This protocol can be merged well with the preceding Cu-catalyzed intermolecular Chan-Evans-Lam cross-coupling reactions, therefore enabling pot-economic modular synthesis of 9-substituted acridines from readily available 2-amino phenyl ketones and aryl boronic acids at room temperature.

Palladium-Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2-Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant

A facile oxidative annulation of cyclohexanones and 2-aminophenyl ketones that uses molecular oxygen as the sole oxidant is described. The reaction provides a direct approach to acridines, a structural motif for a large number of fluorescent sensors, functional materials, ligands, and pharmaceuticals. In the presence of a palladium catalyst, high regioselectivity is observed when using non-symmetric 3-substituted cyclohexanones. With the use of oxygen as the terminal redox moderator, the electron gap of the global redox condensation process is filled and the reaction efficiency is significantly promoted. This protocol possesses many advantages such as using non-hazardous oxidant and readily available starting materials, high regioselectivity, and water as the only by-product. (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.