24429-49-0

Basic information

• Product Name: 2-Anthracenesulfonic acid, 1-amino-9,10-dihydro-9,10-dioxo-, monosodium salt
• Synonyms: Na-1-Amino-anthrachinon-2-sulfonat;1-Amino-9,10-dioxo-9,10-dihydro-anthracen-2-sulfonsaeure, Natrium-Salz;sodium 1-aminoanthraquinone-2-sulfonate;1-amino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid , sodium-salt
• CAS NO: 24429-49-0
• Molecular Formula: C14H9NO5S.Na
• Molecular Weight: 325.277
• Mol File: 24429-49-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Anthracenesulfonic acid, 1-amino-9,10-dihydro-9,10-dioxo-, monosodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Anthracenesulfonic acid, 1-amino-9,10-dihydro-9,10-dioxo-, monosodium salt(24429-49-0)
• EPA Substance Registry System: 2-Anthracenesulfonic acid, 1-amino-9,10-dihydro-9,10-dioxo-, monosodium salt(24429-49-0)

Safety Data

• Hazardous Substances Data: 24429-49-0(Hazardous Substances Data)

Usage

Class

Anthracene derivatives

Common uses

Fluorescent dye for biological staining, pH indicator, synthesis of organic compounds, reagent in analytical chemistry

Solubility

Water-soluble

Specific form

Monosodium salt, highly soluble in aqueous solutions

Potential applications

Photovoltaics, materials science, due to photochemical and photophysical properties

Upstream product

• 66583-20-8 1-amino-2-mercapto-9,10-antraquinone sodium salt 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 
• 82-45-1 1-amino-9,10-anthracenedione 

Downstream Products

• 82-45-1 1-amino-9,10-anthracenedione 
• 81-49-2 1-amino-2, 4-dibromoanthraquinone 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 

Relevant articles and documents

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.

ELECTROCHEMICAL REDUCTION OF SODIUM 1-AMINO-4-BROMO-ANTHRAQUINONE-2-SULFONATE

The product from electrochemical reduction of sodium 1-amino-4-bromoanthraquinone-2-sulfonate in an alkaline medium is sodium 1-aminoanthraquinone-2-sulfonate.In the presence of copper sulfate disodium 4,4'-diamino-1,1'-bianthraquinonyl-3,3'-disulfonate is also formed.In the presence of copper sulfate and oxygen sodium 1-amino-4-hydroxyanthraquinone-2-sulfonate is also formed.It is suggested that during the electrochemical reduction, as in the reduction of 1-amino-4-bromoanthraquinone-2-sulfonic acid with aromatic amines, these products are formed by a mechanism involving an electron transfer stage.