1,5-Dimethoxyanthraquinone

Base Information

• Chemical Name: 1,5-Dimethoxyanthraquinone
• CAS No.: 6448-90-4
• Molecular Formula: C16H12 O4
• Molecular Weight: 268.269
• Hs Code.: 2914690090
• European Community (EC) Number: 229-244-8
• NSC Number: 37606
• DSSTox Substance ID: DTXSID7064364
• Nikkaji Number: J55.390E
• Wikidata: Q81991489
• Mol file: 6448-90-4.mol

Synonyms:1,5-Dimethoxyanthraquinone;1,5-dimethoxyanthracene-9,10-dione;6448-90-4;1,5-Dimethoxyanthrachinon;9,10-Anthracenedione, 1,5-dimethoxy-;1,5-Dimethoxyanthrachinon [Czech];ANTHRAQUINONE, 1,5-DIMETHOXY-;EINECS 229-244-8;NSC 37606;BRN 1914893;4-08-00-03269 (Beilstein Handbook Reference);9, 1,5-dimethoxy-;Anthraquinone,5-dimethoxy-;SCHEMBL3417492;DTXSID7064364;NSC37606;NSC-37606;STK238450;AKOS002384467;1,5-Dimethoxyanthra-9,10-quinone #;WLN: L C666 BV IVJ DO1 KO1;LS-20677;A834774

Chemical Property of 1,5-Dimethoxyanthraquinone

Chemical Property:

• Vapor Pressure: 1.02E-08mmHg at 25°C
• Melting Point: 236°C
• Refractive Index: 1.5447 (estimate)
• Boiling Point: 462.1 °C at 760 mmHg
• Flash Point: 207.9 °C
• PSA: 52.60000
• Density: 1.295 g/cm³
• LogP: 2.47920
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 268.07355886
• Heavy Atom Count: 20
• Complexity: 367

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1C(=O)C3=C(C2=O)C(=CC=C3)OC
• General Description: 1,5-Dimethoxyanthraquinone is a dimethoxy-substituted anthraquinone derivative that serves as a key intermediate in the synthesis of polycyclic aromatic hydrocarbons (PAHs) such as dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes. Through ruthenium-catalyzed C-O arylation, it can be chemoselectively functionalized with arylboronates, enabling further transformations into PAHs with hole-transporting properties, which are relevant for organic semiconductor applications like organic field-effect transistors (OFETs).

Technology Process of 1,5-Dimethoxyanthraquinone

There total 34 articles about 1,5-Dimethoxyanthraquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-hydroxy-5-methoxy-9,10-anthraquinone (52869-21-3) + methyl iodide (74-88-4) → 1,5-dimethoxy-anthraquinone (6448-90-4)

Guidance literature:

With silver(l) oxide; In dichloromethane; for 41h; Ambient temperature;

DOI:10.1021/jo00242a042

Reference yield: 99.0%

sulfonamide + 1.5-dinitroanthraquinone (82-35-9) → 1,5-dimethoxy-anthraquinone (6448-90-4)

Guidance literature:

With potassium hydroxide; In methanol;

Reference yield: 90.0%

1,5-dihydroxyanthraquinone (117-12-4) + dimethyl sulfate (77-78-1) → 1,5-dimethoxy-anthraquinone (6448-90-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 192h; Ambient temperature;

upstream raw materials:

diazomethane

methanol

diethyl ether

1,5-dihydroxyanthraquinone

Downstream raw materials:

1-hydroxy-5-methoxy-9,10-anthraquinone

9,10-Dihydro-3,13-dimethoxy-9,10-<1',2'>benzenoanthracen-1,4-diol

1,5-dimethoxy-9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol

1,5-dimethoxy-anthracene

Refernces

Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C-O Arylation of Dimethoxyanthraquinones

10.1021/acs.orglett.7b01666

This research describes a convenient method for synthesizing dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes, which are polycyclic aromatic hydrocarbons (PAHs) with potential applications as organic semiconductors. The process involves ruthenium-catalyzed chemoselective C?O arylation of dimethoxyanthraquinones with arylboronates, leading to diarylation products that can be further transformed into the target PAHs through a two-step procedure consisting of a Corey?Chaykovsky reaction and subsequent dehydrative aromatization. The synthesized compounds were found to exhibit hole-transporting characteristics, making them suitable for use in organic field-effect transistors (OFETs). Key chemicals used in the process include 1,4- and 1,5-dimethoxyanthraquinones, arylboronates, trimethylsulfonium iodide, sodium hydride, and various Lewis acid catalysts such as InCl3 and SnCl2.