5452-34-6

Basic information

• Product Name: 10,10-dibenzylanthracen-9(10H)-one
• CAS NO: 5452-34-6
• Molecular Formula: C₂₈H₂₂O
• Molecular Weight: 374.4737
• Mol File: 5452-34-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 541.2°C at 760 mmHg
• Flash Point: 234.9°C
• Density: 1.179g/cm³
• Vapor Pressure: 8.87E-12mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: 10,10-dibenzylanthracen-9(10H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 10,10-dibenzylanthracen-9(10H)-one(5452-34-6)
• EPA Substance Registry System: 10,10-dibenzylanthracen-9(10H)-one(5452-34-6)

Safety Data

• Hazardous Substances Data: 5452-34-6(Hazardous Substances Data)

Usage

Appearance

Yellow crystalline solid

Solubility

Sparingly soluble in water, more soluble in organic solvents

Usage

Organic synthesis and chemical research

Structure

Unique structure and reactivity

Potential applications

Materials science, pharmaceuticals, and organic electronics

Fluorescent dye

Investigated for use in biological imaging

Photoinitiator

Studied for use in polymerization reactions

Research interest

Diverse potential uses, of interest to researchers in various fields

Upstream product

• 17407-27-1 10,10-dibenzyl-9,10-dihydroanthracen-9-ol 
• 141377-08-4 9,9-Dibenzyl-10-(trimethylsilyl)-9,10-dihydroanthracene 
• 26908-83-8 9,9-Dibenzyl-9,10-dihydroanthracene 
• 90-44-8 anthracen-9(10H)-one 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 26908-83-8 9,9-Dibenzyl-9,10-dihydroanthracene 
• 2294-89-5 9-benzyl-9,10-dihydroanthracene 
• 17407-27-1 10,10-dibenzyl-9,10-dihydroanthracen-9-ol 
• 78298-98-3 9,10,10-tribenzyl-9-hydroxy-9,10-dihydroanthracene 
• 70674-70-3 9-(2,6-xylyl)-10,10-dibenzyl-9,10-dihydroanthracen-9-ol 
• 127256-89-7 9,10-dibenzyl-9-hydroxy-9,10-dihydroanthracene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 16603-23-9 10-benzyl-9(10H)-anthracenone 
• 84-65-1 9,10-phenanthrenequinone 

Relevant articles and documents

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A Convenient Synthesis of 9,9-Dialkyl-9,10-dihydroanthracenes and 10,10-Dialkylanthrones: Silicon-Mediated Regioselective Dialkylation of 9,10-Dihydroanthracene

Described is a short and convenient approach to the synthesis of 9,9-dialkyl-9,10-dihydroanthracenes, 9,9,10-trialkyl-9,10-dihydroanthracenes, and 10,10-dialkylanthrones, some of which are otherwise unknown or inaccessible by conventional methods.Deprotonation of 9-(trimethylsilyl)-9,10-dihydroanthracene (2; 9-(trimethylsilyl)-9,10-DHA) followed by reaction with alkyl halides (RX) produces 9-alkyl-9-(trimethylsilyl)-9,10-DHAs 3-7 in 80-90percent yields.Treatment of 3-7 with n-BuLi produces the 10-lithio derivatives that rearrange to 9-alkyl-9-lithio-10-(trimethylsilyl) intermediates; subsequent alkylation with RX generates 9,9-dialkyl-10-(trimethylsilyl)-9,10-DHAs 8-19.Formation of single stereoisomers 13-19 was suggested by NMR and confirmed in two cases, 15 and 16, by X-ray structure determination.The trimethylsilyl group is removed by tetrabutylammonium fluoride (TBAF) to provide 9,9-dialkyl-9,10-DHAs 20-29 with impressive yields.Oxidation of either the 9,9-dialkyl-9,10-DHAs or 9,9-dialkyl-10-(trimethylsilyl)-9,10-DHAs with Cr(VI) oxidant furnished 10,10-dialkylanthrones 36-41 in 80-90percent yields.