82-20-2

Basic information

• Product Name: 1,5-bis(4-methylphenyl)amino]anthraquinone
• Synonyms: 9,10-Anthracenedione, 1,5-bis((4-methylphenyl)amino)-; 1,5-Di-p-toluidinoanthraquinone; NSC 13985; Violet 3R base; 1,5-Bis((4-methylphenyl)amino)anthraquinone; Anthraquinone, 1,5-di-p-toluidino- (8CI)
• CAS NO: 82-20-2
• Molecular Formula: C₂₈H₂₂N₂O₂
• Molecular Weight: 418.494
• EINECS: 201-403-6
• Mol File: 82-20-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,5-bis(4-methylphenyl)amino]anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-bis(4-methylphenyl)amino]anthraquinone(82-20-2)
• EPA Substance Registry System: 1,5-bis(4-methylphenyl)amino]anthraquinone(82-20-2)

Safety Data

• Hazardous Substances Data: 82-20-2(Hazardous Substances Data)

Usage

General Description

1,5-bis(4-methylphenyl)amino]anthraquinone, also known as Diketopyrrolopyrrole (DPP), is a red organic pigment that is widely used in the production of inks, coatings, and plastics. It is a semi-conductor material that exhibits strong absorption and emission in the visible region of the electromagnetic spectrum. DPP has good thermal stability and offers excellent light fastness, making it a popular choice for various applications in the printing and packaging industry. Additionally, it is also used in the manufacturing of solar cells and organic light-emitting diodes due to its desirable electronic properties. During its synthesis, 1,5-dialkyl- and 2,6-dialkoxynaphthalenes are converted to 1,5-diketones and 1,5-diaminoanthraquinone, followed by a palladium-catalyzed amination to form the final product, 1,5-bis(4-methylphenyl)amino]anthraquinone.

Upstream product

• 82-46-2 1,5-Dichloroanthraquinone 
• 106-49-0 p-toluidine 
• 82-35-9 1.5-dinitroanthraquinone 
• 117-14-6 1,5-anthraquinone disulfonate 
• 82-21-3 1,5-diphenoxyanthracene-9,10-dione 

Downstream Products

• 117-04-4 NSC 297168 

Relevant articles and documents

Reactions of 1,5-Dichloroanthrachinone with Nucleophiles

Reactions of 1,5-dichloroanthraquinone (1) with various nucleophiles were examined to evaluate possibilities for selective substitution. 1-Amino-5-chloroanthraquinone was obtained from 1 by reaction with (a) sodium azide in dimethyl sulfoxide and (b ammonia in the presence of potassium fluoride, but 1 with potassium in ammonia gave 3-chlorobenzoic acid.Conditions were found for preferential substitution in reactions of 1 with (c) 4-toluidine, (d) hexamethylphosphoric triamide, and (e) N-methylformamide.Reagent e is preferred for making 1-chloro-5-(methylamino)anthraquinone, though this compound predominates in mixtures produced when d is used.Potassium hydroxide in 2-ethoxyethanol converts 1 to the corresponding mono- and diethers of 1,5-dihydroxyanthraquinone, while sodium hydrosulfide and 1 give bis(5-chloroanthraquinonyl)sulfide.