24094-46-0

Basic information

• Product Name: 1-Amino-4-bromo-2-(hydroxymethyl)anthraquinone
• Synonyms: 1-Amino-4-bromo-2-(hydroxymethyl)anthraquinone
• CAS NO: 24094-46-0
• Molecular Formula: C₁₅H₁₀BrNO₃
• Molecular Weight: 332.15
• Mol File: 24094-46-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 238-239 °C(Solv: benzene (71-43-2))
• Boiling Point: 590.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.735±0.06 g/cm3(Predicted)
• PKA: 13.68±0.10(Predicted)
• CAS DataBase Reference: 1-Amino-4-bromo-2-(hydroxymethyl)anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-4-bromo-2-(hydroxymethyl)anthraquinone(24094-46-0)
• EPA Substance Registry System: 1-Amino-4-bromo-2-(hydroxymethyl)anthraquinone(24094-46-0)

Safety Data

• Hazardous Substances Data: 24094-46-0(Hazardous Substances Data)

Upstream product

• 81-62-9 1-amino-4-bromo-9,10-anthracenedione 
• 82-45-1 1-amino-9,10-anthracenedione 
• 24094-44-8 1-amino-2-hydroxymethyl-9,10-dioxo-9,10-dihydroanthracene 

Downstream Products

• 61487-35-2 6-bromo-2-phenyl-1,4-dihydro-2H-anthra[1,2-d][1,3]oxazine-7,12-dione 
• 76260-09-8 6-Bromo-2,2-diphenyl-1,4-dihydro-2H-anthra[1,2-d][1,3]oxazine-7,12-dione 
• 76260-00-9 6-Bromo-2-methyl-2-phenyl-1,4-dihydro-2H-anthra[1,2-d][1,3]oxazine-7,12-dione 

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.