56799-32-7

Basic information

• Product Name: 1,4-bis(dimethylamino)anthraquinone
• Synonyms: 1,4-bis(dimethylamino)anthraquinone;1,4-Bis(dimethylamino)-9,10-anthraquinone;9,10-Anthracenedione, 1,4-bis(dimethylamino)-;Einecs 260-388-4
• CAS NO: 56799-32-7
• Molecular Formula: C₁₈H₁₈N₂O₂
• Molecular Weight: 294.34772
• EINECS: 260-388-4
• Mol File: 56799-32-7.mol

Chemical Properties

• Boiling Point: 488.1°Cat760mmHg
• Flash Point: 223.1°C
• Appearance: /
• Density: 1.252g/cm³
• Vapor Pressure: 1.12E-09mmHg at 25°C
• Refractive Index: 1.665
• CAS DataBase Reference: 1,4-bis(dimethylamino)anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis(dimethylamino)anthraquinone(56799-32-7)
• EPA Substance Registry System: 1,4-bis(dimethylamino)anthraquinone(56799-32-7)

Safety Data

• Hazardous Substances Data: 56799-32-7(Hazardous Substances Data)

Usage

Type of compound

Derivative of anthraquinone (a polycyclic aromatic hydrocarbon)

Common use

Blue dye in the textile industry

Characteristic property

Strong color

Utilization

Production of dyes and pigments for various applications

Potential application

Organic electronic devices (due to favorable electron-transporting properties)

Safety considerations

Specific handling and storage requirements; potential hazards; proper safety precautions necessary

InChI:InChI=1/C18H18N2O2/c1-19(2)13-9-10-14(20(3)4)16-15(13)17(21)11-7-5-6-8-12(11)18(16)22/h5-10H,1-4H3

Upstream product

• 96701-06-3 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl bis(4-methylbenzenesulfonate) 
• 124-40-3 dimethyl amine 
• 28736-42-7 1,4-difluoroanthracene-9,10-dione 
• 57-14-7 N,N-Dimethylhydrazine 

Relevant articles and documents

Influence of different amino substituents in position 1 and 4 on spectroscopic and acid base properties of 9,10-anthraquinone moiety

A series of novel 1-amino and 1,4-diamino-9,10-anthraquinones, substituted with different alkyl groups, were synthesized as the result of alkylation with amino substituents. All the obtained aminoanthraquinone derivatives were characterized by NMR, IR spectroscopy and mass spectrometry. The spectroscopic properties of these compounds were determined by using UV-Vis spectroscopy in acetonitrile, and in the mixture of acetonitrile and methanol at different pH ranges. The effects of various substituents present in the newly developed anthraquinone derivatives and their ability to form hydrogen bonds between the carbonyl oxygen atom of anthraquinone moiety and nitrogen atom of N-H group in 1-aminoanthraquinone (1-AAQ) and 1,4-diaminoanthraquinone (1,4-DAAQ) were studied. Additionally, the effects of hydrogen bond formation between O-H group in hydroxyethylamino substituent and the carbonyl oxygen atom of anthraquinone were investigated. The spectroscopic behavior of the studied derivatives strongly depended on the solvent-solute interactions and the nature of solvent. The values of pKa for the new anthraquinones were determined by the combined potentiometric and spectrophotometric titration methods.

Formation of N-N and N-C Bond-Cleavage Products in Displacements with N,N-Disubstituted Hydrazines on 1-Halo- or 1,4-Dihaloanthracene-9,10-diones

The displacements of 1-halo- and 1,4-dihaloanthracene-9,10-diones by N,N-disubstituted hydrazines have been studied.These reactions proceed via N-N bond cleavages of the hydrazine to yield products with the regiospecific incorporation of an N,N-disubstituted amino group.In addition, pyrazoles which arise from intermediates which undergo N-C bond cleavage are also formed.The ratio of the N-N to N-C cleavage products is dependent on the reaction solvent, temperature, structure of the hydrazine, and the nature of the leaving group being displaced from the anthracene-9,10-dione.For example, treatment of 1a with N,N-dimethylhydrazine in pyridine or dimethyl sulfoxide (DMSO) leads to 3a:2c ratios of 6 and 3, respectively.Compound 1e under comparable reaction conditions gives 3a:2c product ratios of 49 and 4, respectively.The dichloro dione 1c with N,N-dimethylhydrazine in pyridine or DMSO leads predominantly to 3b in 76percent and 72percent yields, respectively, with relatively little pyrazole 2d.The more reactive difluoro dione 1h on reaction with N,N-dimethylhydrazine in pyridine leads to N-N bond-cleavage products 3c (48percent) and 3d (40percent).Treatment of 1e with 1-piperidinamine in pyridine yields 3f.The results will be discussed.