79207-97-9

Basic information

• Product Name: 1,4-bis(prop-2-en-1-yloxy)anthracene-9,10-dione
• Synonyms: 1,4-Bis(allyloxy)-9,10-anthraquinone; 9,10-anthracenedione, 1,4-bis(2-propen-1-yloxy)-
• CAS NO: 79207-97-9
• Molecular Formula: C₂₀H₁₆O₄
• Molecular Weight: 320.3386
• Mol File: 79207-97-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 495.7°C at 760 mmHg
• Flash Point: 219.3°C
• Density: 1.216g/cm³
• Vapor Pressure: 5.77E-10mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 1,4-bis(prop-2-en-1-yloxy)anthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis(prop-2-en-1-yloxy)anthracene-9,10-dione(79207-97-9)
• EPA Substance Registry System: 1,4-bis(prop-2-en-1-yloxy)anthracene-9,10-dione(79207-97-9)

Safety Data

• Hazardous Substances Data: 79207-97-9(Hazardous Substances Data)

Usage

Derivative of

Anthracene

Physical state

Crystalline solid

Color

Yellow

Odor

Strong aromatic

Primary uses

a. Production of dyes and pigments
b. Manufacturing of optical brighteners and fluorescent whitening agents
c. Synthesis of organic semiconductors
d. Fluorescent probe in biological imaging

Potential applications

a. Electroluminescent devices
b. Photoactivator in photodynamic therapy

Safety concerns

Health and environmental risks due to chemical properties

Handling

Caution required

Upstream product

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 106-95-6 allyl bromide 

Downstream Products

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 79208-09-6 1,4-dihydroxy-2-(prop-2'-enyl)-9,10-anthraquinone 
• 79208-01-8 2,3-diallyl-1,4-dihydroxyanthraquinone 
• 79208-08-5 1-hydroxy-4-propanoyl-2-(prop-2'-enyl)anthraquinone 
• 79207-99-1 1-hydroxy-4-(prop-2'enyoxy)-9,10-anthraquinone 
• 79208-02-9 1-hydroxy-2-(prop-1'-enyl)-4-(prop-2''-enyloxy)anthraquinone 
• 79208-03-0 1,4-dihydroxy-2-(prop-1'-enyl)-3-(prop-2''-enyl)anthraquinone 
• 98298-55-6 1,4-bis(2′,3′-epoxymethoxy)anthracene-9,10-dione 
• 58976-87-7 1,4-dihydro-5,12-dihydroxynaphthacene-6,11-dione 
• 58976-90-2 5,12-diacetoxy-1,4-dihydronaphthacene-6,11-dione 

Relevant articles and documents

Quinizarin Derivatives as Photoinitiators for Free-Radical and Cationic Photopolymerizations in the Visible Spectral Range

We report the use of efficient visible-light sensitive allyl (QA) and epoxidized (QE) quinizarin derivatives as photoinitiating systems when combined with an appropriate electron donor (methyldiethanol amine, MDEA), an electron acceptor (iodonium salt, Iod), or a H donor (thiol derivative), for free-radical photopolymerization (FRP), cationic photopolymerization (CP), and a thiol-ene process. These systems have demonstrated excellent initiating properties under air or in laminated conditions under visible-light irradiation (LEDs?405, 455, and 470 nm or Xe lamp) for FRP, CP, or the thiol-ene process and appear more efficient than the well-known camphorquinone-based photoinitiating systems. As highlighted by electron paramagnetic resonance (EPR) and laser flash photolysis experiments, QA (or QE) acts either as an electron donor via a photoinduced electron transfer pathway with Iod or as a proton/proton-coupled electron transfer promoter with MDEA or a thiol derivative. Two types of interpenetrated polymer networks have been synthesized either by CP and the thiol-ene process with di(ethylene glycol) divinyl ether/trithiol or by a concomitant free-radical and cationic photopolymerization with an epoxide/acrylate blend mixture upon LED?455 or 470 nm exposure. Interestingly, the resulting quinizarin-derived materials showed antiadherence properties under visible-light exposure even after two cycles of antibacterial experiments. Quinizarin derivatives can not only initiate photopolymerization but also generate singlet oxygen on the surface of the materials for preventing the adhesion and proliferation of bacteria under visible-light activation.

Novel Chloroanthracyclines from Acetal-Alkene Cyclization

Quinizarin is converted in seven steps into the homochiral acetal (3) in 69percent yield.Methallylation of (3) and reductive Claisen rearrangement gives (4) which is converted into four novel diastereomeric 9-chloroanthracyclines (7-10) by an unprecedented intramolecular acetal-alkene cyclization mediated by tin(IV) chloride in DMF.

A new protocol for benzoannulation by double Claisen rearrangement and ring-closing metathesis reactions as key steps

A new methodology for benzoannulation has been developed by using double Claisen rearrangement followed by a one-pot ring-closing metathesis and DDQ oxidation sequence.