6258-06-6

Basic information

• Product Name: 1-AMINO-4-BROMOANTHRAQUINONE-2-SULFONIC ACID SODIUM SALT
• Synonyms: 1-amino-4-bromanthrachinon-2-sulfonansodny;1-amino-4-bromo-9,10-dihydro-9,10-dioxo-2-anthracenesulfonicacimonosodi;1-amino-4-bromo-9,10-dihydro-9,10-dioxo-2-anthracenesulfonicacimonosodium;2-Anthracenesulfonicacid,1-amino-4-bromo-9,10-dihydro-9,10-dioxo-,monosodiumsalt;9,10-dihydro-1-amino-4-bromo-9,10-dioxo-2-anthracenesulfonicacisodiumsal;bromaminansodny;1-AMINO-4-BROMO-2-ANTHRAQUINONE-SULFONIC ACID SODIUM SALT;1-AMINO-4-BROMO-9,10-DIHYDRO-9,10-DIOXO-2-ANTHRACENESULFONIC ACID, SODIUM SALT
• CAS NO: 6258-06-6
• Molecular Formula: C₁₄H₇BrNO₅S*Na
• Molecular Weight: 404.17
• EINECS: 228-391-5
• Product Categories: Anthraquinonesulfonic Acids;Aminoanthraquinones;Anthraquinones
• Mol File: 6258-06-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: >300 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 1-AMINO-4-BROMOANTHRAQUINONE-2-SULFONIC ACID SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINO-4-BROMOANTHRAQUINONE-2-SULFONIC ACID SODIUM SALT(6258-06-6)
• EPA Substance Registry System: 1-AMINO-4-BROMOANTHRAQUINONE-2-SULFONIC ACID SODIUM SALT(6258-06-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• RTECS: CB1090000
• Hazardous Substances Data: 6258-06-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-AMINO-4-BROMOANTHRAQUINONE-2-SULFONIC ACID SODIUM SALT is used as a reactant for the preparation of aminoanthraquinone derivatives. These derivatives are potent and selective antagonists for the UTP-Activated P2Y4 Receptor, which play a crucial role in various physiological processes and therapeutic applications.
Used in Dye Industry:
1-AMINO-4-BROMOANTHRAQUINONE-2-SULFONIC ACID SODIUM SALT is utilized as a key component in the synthesis of dyes. Its unique chemical properties enable the creation of dyes with specific characteristics, making it a valuable asset in the development of new and improved dye formulations.
Used in Metabolite Research:
In the field of metabolite research, 1-AMINO-4-BROMOANTHRAQUINONE-2-SULFONIC ACID SODIUM SALT serves as a vital compound for studying the metabolic pathways and interactions of various biological systems. Its role in this area is essential for understanding the complex processes that occur within living organisms and can contribute to the development of new therapeutic strategies and diagnostic tools.

InChI:InChI=1/C14H8BrNO5S.Na/c15-8-5-9(22(19,20)21)12(16)11-10(8)13(17)6-3-1-2-4-7(6)14(11)18;/h1-5H,16H2,(H,19,20,21);/q;+1/p-1

Upstream product

• 83-62-5 1-aminoanthraquinone-2-sulfonic acid 
• 82-45-1 1-amino-9,10-anthracenedione 
• 24429-49-0 sodium 1-amino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 

Downstream Products

• 83-62-5 1-aminoanthraquinone-2-sulfonic acid 
• 4095-85-6 1,4-diamino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid 
• 24429-49-0 sodium 1-amino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 25492-62-0 sodium 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 6022-22-6 disodium 4,4'-diamino-1,1'-bianthraquinonyl-3,3'-disulfonate 
• 34824-60-7 Sodium; 1-amino-4-ethylamino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonate 
• 2786-71-2 1-amino-4-anilino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid 
• 34940-32-4 Natrium-Salz von 1-Amino-4-methylamino-9,10-dioxo-9,10-dihydroanthracen-2-sulfonsaeure 
• 20349-48-8 disodium 1-amino-4-(4-amino-2-sulfophenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 15827-21-1 disodium 1-amino-4-(4-amino-3-sulfophenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 50314-37-9 sodium 1-amino-4-(4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 40951-76-6 sodium 1-amino-4-((4-aminophenyl)amino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 78510-27-7 sodium 1-amino-4-(2-methoxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 

Relevant articles and documents

Preparation process for sodium 1-amino-4-bromoanthraquinone-2-sulfonate

The invention discloses a preparation process for sodium 1-amino-4-bromoanthraquinone-2-sulfonate. The preparation process comprises the following steps: (1) sulfonation: with 1-aminoanthraquinone as a raw material, copper sulfate as a catalyst and dichloroethane as a solvent, carrying out dehydration, then adding chlorosulfonic acid drop by drop for a sulfonation reaction, adding 98% concentrated sulfuric acid after completion of the reaction, extracting 1-aminoanthraquinone-2-sulfonic acid out, allowing 1-aminoanthraquinone-2-sulfonic acid to enter the concentrated sulfuric acid, separating out an acid phase at a lower layer and subjecting the acid phase to a subsequent reaction; (2) bromination: adding bromine into the concentrated sulfuric acid solution of 1-aminoanthraquinone-2-sulfonic acid drop by drop for a reaction so as to obtain the concentrated sulfuric acid solution of bromoamine acid; (3) dilution: adding water into the concentrated sulfuric acid solution of bromoamine acid for dilution and successively carrying out cooling, crystallization and filtering so as to obtain bromoamine acid; and (4) salt formation: adding water to dissolve bromoamine acid and adding sodium sulfite to obtain bromoamine acid sodium salt. The preparation process provided by the invention can reduce energy consumption during solvent recovery; the utilization rate of bromine in bromination is high; sodium sulfite is used for salt formation, so the amount of impurities is reduced; and product quality is high.

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs

Anthraquinone (AQ) derivatives play a prominent role in medicine and also in textile industry. Bromaminic acid (1-amino-4-bromoanthraquinone-2-sulfonic acid) is an important precursor for obtaining dyes as well as biologically active compounds through the replacement of the C4-bromo substituent with different (ar)alkylamino residues. Here we report methods for the synthesis of bromaminic acid analogues bearing different substituents at the 2-position of the anthraquinone core. 1-Aminoanthraquinone was converted to its 2-hydroxymethyl-substituted derivative which, under different reaction conditions, yielded the corresponding carbaldehyde, carboxylic acid, and nitrile derivatives. The latter was further reacted to obtain 1-amino-2-tetrazolylanthraquinone. Subsequent bromination using bromine in DMF led to the corresponding bromaminic acid derivatives in excellent isolated yields (>90%) and high purities. Alternatively, 1-amino-4-bromo-2-hydroxymethylanthraquinone could be directly converted to the desired 2-substituted bromaminic acid analogues in high yields (85-100%). We additionally report the preparation of bromaminic acid sodium salt and 1-amino-2,4-dibromoanthraquinone directly from 1-aminoanthraquinone in excellent yields (94-100%) and high purities. The synthesized brominated AQs are valuable precursors for the preparation of AQ drugs and dyes.

OPTIMIZATION OF THE OXIDATIVE BROMINATION OF 1-AMINOANTHRAQUINONE-2-SULFONIC ACID

An efficient method of synthesis of 1-amino-4-bromoanthraquinone-2-sulfonic acid using bromination of the corresponding aminoathraquinonesulfonic acid with bromine in the presence of hydrogen peroxide has been proposed.The optimum conditions of synthesis, with a yield of the target product of 68percent, have been found.

Process for separating off 1-amino-4-bromoanthraquinone-2-sulphonic acid

A process for separating off 1-amino-4-bromoanthraquinone-2-sulphonic acid from the reaction mixture formed by the bromination of 1-aminoanthraquinone-2-sulphonic acid in sulphuric acid, which process comprises adjusting the sulphuric acid concentration of the reaction mixture under the prevailing conditions of temperature and pressure to effect precipitation of 1-amino-4-bromoanthraquinone-2-sulphonic acid as the sulphate and thereafter separating the resultant sulphate precipitate from the reaction mixture.