2395-97-3

Basic information

• Product Name: 9,10-DiMethoxyanthracene
• Synonyms: 9,10-DiMethoxyanthracene
• CAS NO: 2395-97-3
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28116
• Mol File: 2395-97-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 411.4°C at 760 mmHg
• Flash Point: 175.4°C
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 1.33E-06mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: 9,10-DiMethoxyanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DiMethoxyanthracene(2395-97-3)
• EPA Substance Registry System: 9,10-DiMethoxyanthracene(2395-97-3)

Safety Data

• Hazardous Substances Data: 2395-97-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H14O2/c1-17-15-11-7-3-5-9-13(11)16(18-2)14-10-6-4-8-12(14)15/h3-10H,1-2H3

Upstream product

• 40628-55-5 9,10-dimethoxy-9,10-dihydro-9,10-epidioxidoanthracene 
• 13715-60-1 9,10-dimethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 67-56-1 methanol 
• 120-12-7 anthracene 
• 113160-89-7 C₂₁H₂₂O₄ 

Downstream Products

• 84-65-1 9,10-phenanthrenequinone 
• 68818-86-0 9,10-Diethoxyanthracene 
• 13715-60-1 9,10-dimethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 189502-14-5 10-Methoxy-[9]anthrol 
• 30122-23-7 C₁₉H₁₈O₂ 
• 153507-77-8 (n-Bu₃P)2Ni⁽⁰⁾(9,10-dimethoxyanthracene) 
• 96555-78-1 11,12-dibenzoyl-9,10-dihydro-9,10-dimethoxy-9,10-ethenoanthracene 

Relevant articles and documents

Intermediates in the cleavage of endoperoxides

The decomposition of anthracene endoperoxides has been investigated under various conditions. Thermolyses proceed via radical intermediates and afford anthracenes and rearrangement products, depending on the substitution pattern. Interestingly, not only the O–O but also the C–O bond can be cleaved homolytically. Under basic conditions fragmentations take place, affording anthraquinone, and reactive oxygen species. This mechanism explains the often observed decomposition of endoperoxides during work-up. Finally, an acid-catalyzed cleavage has been observed under release of hydrogen peroxide. The results should be interesting for the mechanistic understanding of peroxide decomposition and the endoperoxides might serve as mild sources of reactive oxygen species for future applications. Copyright

Electrophilic aromatic addition reaction (AdEAr) to anthracene

After finding in a previous study that naphthalene and quinoline can react via electrophilic aromatic addition reaction (AdEAr), we applied this to anthracene. When anthracene was reacted with bromine in methanol in the presence of NaHCO3 and pyridine, 9,10-dihydro-9,10-dimethoxyanthracene (2) was obtained in 82% yield in the absence of substitution products or oxidative demethylation products like anthraquinone. The same reaction in ethanol produced 9,10-diethoxy-9,10-dihydroanthracene (9) in much lower yield (45%). In addition, we investigated the reactivity of addition product 2. Treatment of 2 with DDQ in benzene at 65 °C for 12 h produced 9,10-dimethoxyanthracene (3) in 62% yield, and 2 was rapidly transformed to 9-methoxyanthracene (4) in methanolic NaOH in 10 min. Moreover, the acid-catalyzed aromatization of 2 in 1-propanol at 75 °C for 10 min gave 9-n-propoxyanthracene (8) in 65% yield.