6363-90-2

Basic information

• Product Name: 1-amino-4-bromo-9,10-dioxo-9,10-dihydroan thracene-2-carboxylic acid
• Synonyms: 2-anthracenecarboxylic acid, 1-amino-4-bromo-9,10-dihydro-9,10-dioxo-
• CAS NO: 6363-90-2
• Molecular Formula: C₁₅H₈BrNO₄
• Molecular Weight: 346.1323
• Mol File: 6363-90-2.mol

Chemical Properties

• Boiling Point: 613.3°Cat760mmHg
• Flash Point: 324.7°C
• Appearance: /
• Density: 1.821g/cm³
• Vapor Pressure: 6.76E-16mmHg at 25°C
• Refractive Index: 1.751
• CAS DataBase Reference: 1-amino-4-bromo-9,10-dioxo-9,10-dihydroan thracene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-4-bromo-9,10-dioxo-9,10-dihydroan thracene-2-carboxylic acid(6363-90-2)
• EPA Substance Registry System: 1-amino-4-bromo-9,10-dioxo-9,10-dihydroan thracene-2-carboxylic acid(6363-90-2)

Safety Data

• Hazardous Substances Data: 6363-90-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H8BrNO4/c16-9-5-8(15(20)21)12(17)11-10(9)13(18)6-3-1-2-4-7(6)14(11)19/h1-5H,17H2,(H,20,21)

Upstream product

• 82-24-6 1-aminoanthraquinone-2-carboxylic acid 
• 82-45-1 1-amino-9,10-anthracenedione 
• 24094-44-8 1-amino-2-hydroxymethyl-9,10-dioxo-9,10-dihydroanthracene 
• 24094-46-0 1-amino-4-bromo-2-(hydroxymethyl)anthraquinone 

Downstream Products

• 1052087-99-6 sodium 1-amino-4-[4-phenylamino-3-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 21200-27-1 1-amino-4-bromo-N-cyclohexyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 

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.

TRANSFORMATIONS OF 1-AZIDOANTHRAQUINONES IN HYDROHALIC ACIDS

When heated in hydrohalic acids, 1-azidoanthraquinones are converted into 1-amino-4-halogenoanthraquinones.Under these conditions the 4-substituted azides are converted into the corresponding 2-halogeno-1-aminoanthraquinones.The kinetic data indicate the intermediate formation of N-halogenoaminoanthraquinones.