1,4-Dimethoxyanthraquinone

Base Information

• Chemical Name: 1,4-Dimethoxyanthraquinone
• CAS No.: 6119-74-0
• Molecular Formula: C16H12O4
• Molecular Weight: 268.269
• NSC Number: 103059,216073
• DSSTox Substance ID: DTXSID80295558
• Nikkaji Number: J81.147E
• Wikidata: Q82035541
• ChEMBL ID: CHEMBL570408
• Mol file: 6119-74-0.mol

Synonyms:1,4-Dimethoxyanthraquinone;1,4-dimethoxyanthracene-9,10-dione;6119-74-0;CHEMBL570408;9, 1,4-dimethoxy-;Quinizarin, dimethyl ether;Anthraquinone,4-dimethoxy-;NSC216073;9,10-Anthracenedione, 1,4-dimethoxy-;CBMicro_020386;1,4 dimethoxyanthraquinone;NCIOpen2_007255;MLS000576106;cid_266054;SCHEMBL3417221;DTXSID80295558;HWHFKYJAAJPFQF-UHFFFAOYSA-N;HMS2356I18;1,4-DIMETHOXY-ANTHRAQUINONE;1,4-dimethoxyanthra-9,10-quinone;CCG-5086;BDBM50303182;NSC103059;STK367471;AKOS005443873;NSC-103059;NSC-216073;SMR000184797;BIM-0020412.P001;CS-0358045

Chemical Property of 1,4-Dimethoxyanthraquinone

Chemical Property:

• Vapor Pressure: 1.02E-08mmHg at 25°C
• Boiling Point: 462.1°C at 760 mmHg
• Flash Point: 207.9°C
• PSA: 52.60000
• Density: 1.295g/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:

99% ^*data from raw suppliers

1,4-DIMETHOXY-ANTHRAQUINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C(=C(C=C1)OC)C(=O)C3=CC=CC=C3C2=O

Technology Process of 1,4-Dimethoxyanthraquinone

There total 28 articles about 1,4-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%

1,4-Dimethoxyspirodioxolan>-10-one (71192-84-2) → 1,4-dimethoxyanthraquinone (6119-74-0)

Guidance literature:

With hydrogenchloride; for 15h; Ambient temperature;

DOI:10.1021/jo00337a002

Reference yield: 99.0%

1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8) + dimethyl sulfate (77-78-1) → 1,4-dimethoxyanthraquinone (6119-74-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 480h; Ambient temperature;

Reference yield: 96.0%

1,4,9,10-tetramethoxy-anthracene (106752-92-5) → 1,4-dimethoxyanthraquinone (6119-74-0)

Guidance literature:

With copper(II) nitrate; In tetrachloromethane; for 0.25h; Heating;

DOI:10.1055/s-1990-27101

upstream raw materials:

1-chloro-4-methoxy-anthraquinone

sodium methylate

2-(2,5-dimethoxybenzoyl)benzoic acid

1,4-dihydroxy-9,10-anthracenedione

Downstream raw materials:

D and C green 6

1,4-dimethoxyanthracene

cis-9,10-diethyl-9,10-dihydro-1,4-dimethoxyanthracene-9,10-diol

trans-9,10-diethyl-9,10-dihydro-1,4-dimethoxyanthracene-9,10-diol

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.

Lithiation Reaction of 2,5-Dibromothiophene. 13C NMR Spectra of 3-Substituted Derivatives

10.1021/jo00200a048

The research focuses on the synthesis and evaluation of unsymmetrical 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones for their potential antineoplastic activity. The purpose is to further define the structure-activity relationship of this class of antitumor agents by developing a convenient two-step synthetic sequence starting with 1,4-dimethoxyanthracene-9,10-dione (2). This method allows for the preparation of both symmetrical and unsymmetrical analogues. The process involves photolytic substitution of 2 in the presence of various primary alkylamines to form monosubstituted products, followed by thermal substitution to yield the desired unsymmetrical 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones.