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

General 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. Its main applications include use as a colorant in the production of inks, textiles, and plastics. Additionally, it is utilized in the manufacturing of paints, coatings, and cosmetics. Bromaminic acid is also employed as a pH indicator, in biological staining procedures, and as a reagent in organic synthesis. 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

• 103566-93-4 furan-2,5-dicarboxylic acid bis-(4-anilino-2-bromo-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 103443-08-9 N,N'-bis-(4-anilino-2-bromo-9,10-dioxo-9,10-dihydro-[1]anthryl)-terephthalamide 
• 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 
• 90791-34-7 1-Amino-2-(4-hydroxy-phenoxy)-4-phenylamino-anthraquinone 
• 90791-32-5 1-Amino-2-(4-methoxy-phenoxy)-4-phenylamino-anthraquinone 
• 90791-35-8 1-Amino-2-(4-amino-phenoxy)-4-phenylamino-anthraquinone 
• 90791-31-4 1-Amino-4-phenylamino-2-p-tolyloxy-anthraquinone 
• 90791-33-6 1-amino-2-<(3-methoxyphenyl)-oxy>-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.