14569-45-0

Basic information

• Product Name: 5,8-dioxo-5,8-dihydronaphthalene-1,4-diyl diacetate
• Synonyms: 1,4-Naphthoquinone, 5,8-dihydroxy-, diacetate; Naphthazarin diacetate
• CAS NO: 14569-45-0
• Molecular Formula: C₁₄H₁₀O₆
• Molecular Weight: 274.2256
• Mol File: 14569-45-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 482.5°C at 760 mmHg
• Flash Point: 218°C
• Density: 1.386g/cm³
• Vapor Pressure: 1.82E-09mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: 5,8-dioxo-5,8-dihydronaphthalene-1,4-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-dioxo-5,8-dihydronaphthalene-1,4-diyl diacetate(14569-45-0)
• EPA Substance Registry System: 5,8-dioxo-5,8-dihydronaphthalene-1,4-diyl diacetate(14569-45-0)

Safety Data

• Hazardous Substances Data: 14569-45-0(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 10075-68-0 1,4,5,8-tetramethoxynaphthalene 
• 65978-30-5 1,4-diacetoxy-5,8-dimethoxynaphthalene 
• 15013-16-8 5,8-dimethoxynaphthoquinone 
• 58851-76-6 4-acetyloxy-5,8-dihydronaphthalen-1-yl acetate 

Downstream Products

• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 87712-25-2 1,4-diacetoxy-5-hydroxy-9,10-anthraquinone 
• 1399290-42-6 (R)-tert-butyl-3-(1,4-dioxo-5,8-bis(2-oxopropyl)-1,4-dihydronaphthalen-2-yl)-2-oxo-3-phenylindoline-1-carboxylate 
• 2289-36-3 1,4-diacetoxy-9,10-anthraquinone 
• 161690-59-1 Acetic acid 8-acetoxy-4,9-dioxo-3-phenyl-3a,4,9,9a-tetrahydro-naphtho[2,3-d]isoxazol-5-yl ester 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 27573-16-6 5-nitro-1,4-dihydroxy-9,10-anthracenedione 
• 117554-15-1 Acetic acid 4-hydroxy-5-nitro-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester 
• 117554-14-0 Acetic acid 4-hydroxy-8-nitro-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester 
• 84525-51-9 Benzoic acid (1S,4R,4aS,9aR)-5,8-diacetoxy-4-ethoxycarbonylamino-9,10-dioxo-1,4,4a,9,9a,10-hexahydro-anthracen-1-yl ester 

Relevant articles and documents

A convenient and efficient synthesis of naphthazarin

A convenient and efficient synthetic method of the important intermediate naphthazarin is presented starting from 1, 4, 5, 8-tetramethoxynaphthalene in an overall yield of 87%. Compared with the reported synthesis, this method has several advantages. Firstly, the reaction conditions are milder; secondly, the workup of each step is simpler and the yield is considerably higher; thirdly, all the reactions involved in the method are more suitable for large-scale preparations.

Synthetic Anthracyclinones, XIII. Regioselective Synthesis of Digitopurpone and Islandicin by a Combined Diels-Alder and Marschalk Reaction

The 1,4-ethanoanthraquinone 5b was obtained by regioselective Diels-Alder reaction of the diene 2 with naphthazarin monoethyl ether (1b) followed by hydroxymethylation of the adduct 3b.Clevage of the ether, retrodiene reaction, and reduction gave digitopurpone (7e).Islandicin (8e) was prepared by a similar sequence starting from 4.Both natural products were free of isomers.