88051-28-9

Basic information

• Product Name: NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN
• Synonyms: NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN;Naphtho[1,8-de:4,5-de]bis([1,3]dioxine)
• CAS NO: 88051-28-9
• Molecular Formula: C12H8O4
• Molecular Weight: 216.191
• Mol File: 88051-28-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 149-151℃
• Appearance: /
• Density: 1.481
• CAS DataBase Reference: NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN(CAS DataBase Reference)
• NIST Chemistry Reference: NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN(88051-28-9)
• EPA Substance Registry System: NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN(88051-28-9)

Safety Data

• Hazardous Substances Data: 88051-28-9(Hazardous Substances Data)

Usage

General Description

Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin, also known as Naphtho[8,1-de][1,3]dioxin, is a synthetic organic compound that belongs to the dioxin family. It is a highly toxic and persistent environmental contaminant that can accumulate in the fatty tissues of animals, including humans, and has been linked to various adverse health effects, including cancer, reproductive and developmental problems, and immune system disruption. Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin is formed as a by-product of industrial processes such as waste incineration, metal smelting, and pesticide production. Due to its toxicity and environmental persistence, it is considered a significant concern for public health and the environment, and efforts to reduce its production and release are ongoing.

Upstream product

• 5690-27-7 1,4,5,8-Tetrahydroxynaphthalene 
• 74-95-3 1,1-dibromomethane 
• 74-97-5 chlorobromomethane 
• 4988-51-6 5,8-dihydroxy-2,3-dihydro-[1,4]naphthoquinone 

Downstream Products

• 517-88-4 (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione 
• 517-89-5 shikonin 
• 88051-30-3 2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene 

Relevant articles and documents

Formal total syntheses of alkannin and shikonin

A short synthesis of a key intermediate in Nicolaou's syntheses of alkannin and shikonin is described.

Enantioselective Total Syntheses of (R)- A nd (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product

Both isomers of naphthotectone, an isoprenoid quinone from Verbenaceae Tectona grandis possessing interesting biological activities, were enantioselectively obtained by two different synthetic routes in which the carbon side-chain of the naphthoquinone core was introduced using either a Sonogashira or a Heck coupling reaction. In both cases, the naphthoquinone core of the final products was obtained by a late-stage anodic treatment. (R)-Naphthotectone was obtained in six steps from leuconaphthazarin with an overall yield of 38 % and an enantiomeric excess of 86 %. This compound was found to have the same absolute configuration as the natural product at its C-3′ stereogenic center. (S)-Naphthotectone was obtained in five steps from leuconaphthazarin with an overall yield of 36 % and an enantiomeric excess of 80 %. Naphthotectone was synthesized in both racemic and enantioenriched forms by two different synthetic strategies using Pd coupling reactions and anodic treatment as key steps. The stereochemistry of the natural product has been assigned.

Concise and efficient total syntheses of alkannin and shikonin

Two enantiomic natural products with wound-healing properties, alkannin (1) and shikonin (2), are accessible by a short and efficient total synthesis. The success was achieved by a novel protecting system for masking of 5,8-dihydroxy-1,4-naphthoquinones (naphthazarins) and a highly stereoselective ketone reduction.