2289-36-3

Basic information

• Product Name: 1,4-Diacetoxy-9,10-anthraquinone
• Synonyms: 1,4-Diacetoxy-9,10-anthraquinone;Quinizarin diacetate
• CAS NO: 2289-36-3
• Molecular Formula: C₁₈H₁₂O₆
• Molecular Weight: 324.2843
• Mol File: 2289-36-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 524.5°Cat760mmHg
• Flash Point: 234°C
• Appearance: /
• Density: 1.383g/cm³
• Vapor Pressure: 4.27E-11mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 1,4-Diacetoxy-9,10-anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Diacetoxy-9,10-anthraquinone(2289-36-3)
• EPA Substance Registry System: 1,4-Diacetoxy-9,10-anthraquinone(2289-36-3)

Safety Data

• Hazardous Substances Data: 2289-36-3(Hazardous Substances Data)

Usage

Chemical compound

Yes

Primary use

Dye intermediate and production of certain pigments

Derived from

Anthraquinone

Anthraquinone use

Production of dyes and pigments

Color

Red-brown

Application in textile industry

Dyeing natural fibers like cotton and wool

Other uses

Production of colored inks and paints

Potential applications

Organic semiconductors and organic electronic devices

InChI:InChI=1/C18H12O6/c1-9(19)23-13-7-8-14(24-10(2)20)16-15(13)17(21)11-5-3-4-6-12(11)18(16)22/h3-8H,1-2H3

Upstream product

• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 14569-45-0 5,8-diacetoxy-1,4-naphthoquinone 
• 15910-11-9 1,4-diacetoxy 1,3-butadiene 
• 24301-50-6 anthracene-1,4-diacetate 
• 37845-21-9 5.8-dihydroxy-1.4-dihydro-anthraquinone 
• 64-19-7 acetic acid 

Downstream Products

• 3786-46-7 3,6-dihydroxyphthalic acid 
• 74553-57-4 9-hydroxy-1,4-anthraquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 98771-41-6 9,10-di(p-tolylamino)-1,4-anthraquinone 
• 100073-85-6 N-(p-tolyl)-1,4-dihydroxy-9,10-anthraquinone 9-imine 

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).