1564-71-2

Basic information

• Product Name: 1-amino-2-bromo-4-(phenylamino)anthraquinone
• Synonyms: 1-amino-2-bromo-4-(phenylamino)anthraquinone;1-amino-2-bromo-4-(phenylamino)anthracene-9,10-dione;9,10-Anthracenedione, 1-amino-2-bromo-4-(phenylamino)-;1-Amino-4-anilino-2-bromoanthraquinone;1-AMINO-2-BROMO-4-(PHENYLAMINO)-9,10-ANTHRACENEDIONE;C.I. Solvent Blue 94
• CAS NO: 1564-71-2
• Molecular Formula: C₂₀H₁₃BrN₂O₂
• Molecular Weight: 393.23342
• EINECS: 216-361-4
• Mol File: 1564-71-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 230 °C(Solv: toluene (108-88-3))
• Boiling Point: 584.1°Cat760mmHg
• Flash Point: 307.1°C
• Appearance: /
• Density: 1.614g/cm³
• Vapor Pressure: 1.24E-13mmHg at 25°C
• Refractive Index: 1.757
• PKA: -1.60±0.20(Predicted)
• CAS DataBase Reference: 1-amino-2-bromo-4-(phenylamino)anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-2-bromo-4-(phenylamino)anthraquinone(1564-71-2)
• EPA Substance Registry System: 1-amino-2-bromo-4-(phenylamino)anthraquinone(1564-71-2)

Safety Data

• Hazardous Substances Data: 1564-71-2(Hazardous Substances Data)

Usage

Description

1-amino-2-bromo-4-(phenylamino)anthraquinone, also known as bromaminic acid, is a chemical compound with the molecular formula C20H13BrN2O2. It is a dark red crystalline solid that is commonly used as a dye and a pigment in various industries.
Used in Ink Production:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used as a colorant for producing inks, providing a dark red hue to the ink formulations.
Used in Textile Industry:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used as a dye in the textile industry, imparting color to fabrics and garments.
Used in Plastics Industry:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used as a pigment in the plastics industry, adding color to various plastic products.
Used in Paint and Coating Manufacturing:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used as a colorant in the production of paints and coatings, contributing to their aesthetic appeal and appearance.
Used in Cosmetics Industry:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used as a colorant in cosmetics, providing a vibrant red shade to various cosmetic products.
Used as a pH Indicator:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used as a pH indicator, detecting changes in acidity or alkalinity in various applications.
Used in Biological Staining Procedures:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used in biological staining procedures, aiding in the visualization of cellular structures and components.
Used as a Reagent in Organic Synthesis:
1-amino-2-bromo-4-(phenylamino)anthraquinone is used as a reagent in organic synthesis, facilitating various chemical reactions and processes.
It is important to handle this chemical with caution, as it is considered to be harmful if swallowed and can cause severe skin and eye irritation upon contact.

InChI:InChI=1/C20H13BrN2O2/c21-14-10-15(23-11-6-2-1-3-7-11)16-17(18(14)22)20(25)13-9-5-4-8-12(13)19(16)24/h1-10,23H,22H2

Upstream product

• 81-49-2 1-amino-2, 4-dibromoanthraquinone 
• 62-53-3 aniline 
• 82-45-1 1-amino-9,10-anthracenedione 
• 3300-23-0 1-amino-2-bromoanthraquinone 

Downstream Products

• 103443-08-9 N,N'-bis-(4-anilino-2-bromo-9,10-dioxo-9,10-dihydro-[1]anthryl)-terephthalamide 
• 90791-36-9 1-Amino-2-{4-[1-(4-hydroxy-phenyl)-1-methyl-ethyl]-phenoxy}-4-phenylamino-anthraquinone 
• 90791-35-8 1-Amino-2-(4-amino-phenoxy)-4-phenylamino-anthraquinone 
• 103566-93-4 furan-2,5-dicarboxylic acid bis-(4-anilino-2-bromo-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 6871-70-1 8,17-dianilino-6,15-dihydro-dinaphtho[2,3-a;2',3'-h]phenazine-5,9,14,18-tetraone 
• 70730-78-8 3-bromo-5-phenylamino-6H-anthra[1,9-cd]isoxazol-6-one 
• 75753-49-0 3-Morpholin-4-yl-5-phenylamino-anthra[1,9-cd]isoxazol-6-one 
• 75753-48-9 5-Phenylamino-3-piperidin-1-yl-anthra[1,9-cd]isoxazol-6-one 
• 75753-50-3 3-Benzylamino-5-phenylamino-anthra[1,9-cd]isoxazol-6-one 
• 75753-53-6 3-Ethylamino-5-phenylamino-anthra[1,9-cd]isoxazol-6-one 
• 75753-52-5 3-Dimethylamino-5-phenylamino-anthra[1,9-cd]isoxazol-6-one 
• 75753-51-4 3-Methylamino-5-phenylamino-anthra[1,9-cd]isoxazol-6-one 
• 32571-82-7 1-Amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracen-2-carbonitril 
• 86397-46-8 1-amino-2-phenoxy-4-anilinoanthraquinone 

Relevant articles and documents

Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes

Novel 1-amino-4-(ar)alkylaminoanthraquinone derivatives bearing different substituents (Br, CH2OH, CN, or CH3) at the 2-position of the anthraquinone scaffold were synthesized by copper-catalyzed Ullmann condensation. The 2-substituted 1-amino-4-bromoanthraquinone derivatives (bromaminic acid analogues) were reacted with a variety of alkyl-, aryl-, and aralkylamines. Different reaction conditions were applied depending on the physical state of the amine and the nature of the substituent at the 2-position of the anthraquinone scaffold. A solvent-free synthetic procedure was developed for reactions with liquid amines. Condensation with solid amines required the addition of a solvent, and reaction conditions had to be optimized for each of the anthraquinone derivatives. Our results emphasize that copper-catalyzed reactions are highly variable depending on the molecules and anions present in the medium, since different reaction mechanisms apply. The synthesized anthraquinone derivatives may be useful as new dyes, or may show biological activity and could be employed as tool compounds in experimental pharmacology.

Arylamination of Aminohalogenoanthraquinones

1-Amino-4-arylaminoanthraquinones (II) have been prepared in high yields by reacting 1-amino-4-chloroanthraquinone (Ia, 1 mol) with arylamines (6 mol) and anhyd.AlCl3 (5 mol) in nitrobenzene at room temperature. 1-Amino-2-bromoanthraquinone, 2-amino-1-chloroanthraquinone, 1-benzamido-4-chloroanthraquinone and 1-amino-5-chloroanthraquinone fail to give arylaminated products. 1-Amino-2,4-dibromoanthraquinone (Ic) gives only 4-arylaminated compounds (IIq-s) whereas 1-amino-8-chloroanthraquinone (Ie) gives 2-arylaminated derivatives (III).A plausible mechanism for the reaction has been suggested.The arylaminated compounds have been applied on polyester as disperse dyes and their dyeing properties evaluated.