63768-01-4

Basic information

• Product Name: 1-(butylamino)-4-hydroxyanthraquinone
• Synonyms: 1-(butylamino)-4-hydroxyanthraquinone;EINECS 264-453-8;1-Butylamino-4-hydroxy-9,10-dihydro-9,10-anthracenedione;1-Hydroxy-4-(butylamino)-9,10-anthraquinone;4-(Butylamino)-1-hydroxy-9,10-anthraquinone
• CAS NO: 63768-01-4
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.33248
• EINECS: 264-453-8
• Mol File: 63768-01-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 517.6°C at 760 mmHg
• Flash Point: 266.8°C
• Appearance: /
• Density: 1.304g/cm³
• Vapor Pressure: 2.48E-11mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: 1-(butylamino)-4-hydroxyanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(butylamino)-4-hydroxyanthraquinone(63768-01-4)
• EPA Substance Registry System: 1-(butylamino)-4-hydroxyanthraquinone(63768-01-4)

Safety Data

• Hazardous Substances Data: 63768-01-4(Hazardous Substances Data)

Usage

General Description

1-(butylamino)-4-hydroxyanthraquinone is a synthetic organic compound that belongs to the anthraquinone class of chemicals. It is used primarily as a dye and colorant in various applications, such as in the production of textiles, plastics, and printing inks. The compound is characterized by its vivid, reddish-brown color and is known for its high stability and resistance to fading. Additionally, it has been found to have potential antioxidant and anti-inflammatory properties, leading to its exploration in the field of pharmaceuticals for potential medicinal uses. However, it is important to note that as with any chemical substance, proper handling and safety precautions should be taken when working with 1-(butylamino)-4-hydroxyanthraquinone to minimize any potential risks to human health and the environment.

InChI:InChI=1/C18H17NO3/c1-2-3-10-19-13-8-9-14(20)16-15(13)17(21)11-6-4-5-7-12(11)18(16)22/h4-9,19-20H,2-3,10H2,1H3

Upstream product

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 109-73-9 N-butylamine 
• 67-56-1 methanol 
• 57-55-6 propylene glycol 
• 129-43-1 1-hydroxyanthraquinone 

Relevant articles and documents

Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions

Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene- 9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1, 4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH2 in the presence of PhI(OAc)2 as catalyst produced seven aminoanthraquinone derivatives 1a, b, 3a, and 5a-d. Amination of 3 and 5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (3a), 2-(butylamino)anthracene-9,10-dione (5a) and 2,3-(dibutylamino)anthracene-9,10-dione (5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones 3a, 5a and 5b exhibited strong cytotoxicity towards both cancer cell lines (IC50 1.1-13.0 μg/mL).

The Direct Alkylamination of α-Substituted Antraquinones Promoted bu Metal Ions

The reaction of 1-amino-4-acylaminoantraquinones with piperidine in the presence of CoCl2 and atmospheric oxygen gave the 2-aminated products in 75-80percent and similar reaction of 1-hydroxyantraquinone or 1-aminoantraquinone-2-sulfonic acid with butylamine gave the corresponding 4-aminated products, respectively.The effects of the α-substituents and the role of metal salts were discussed.