6531-35-7

Basic information

• Product Name: 2,3-DIMETHYLANTHRAQUINONE
• Synonyms: 2,3-DIMETHYLANTHRAQUINONE;DIMETHYLANTHRAQUINONE,2,3-;DIMETHYLANTHRAQUINONE,2,3-(RG);2,3-Dimethyl-9,10-anthracenedione;2,3-Dimethylanthracene-9,10-dione;9,10-Anthracenedione, 2,3-dimethyl-;2,3-Dimethylanthraquinone ,98%;2,3-Dimethylanthraquinone 98%
• CAS NO: 6531-35-7
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.27
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Anthraquinones;Chloroanthraquine, etc.;Highly Purified Reagents;Other Categories;Refined Products by Sublimation;C15 to C38;Carbonyl Compounds;Ketones
• Mol File: 6531-35-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 210-212 °C(lit.)
• Boiling Point: 338.73°C (rough estimate)
• Flash Point: 157.4 °C
• Appearance: /
• Density: 1.1223 (rough estimate)
• Vapor Pressure: 2.69E-07mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: 2,3-DIMETHYLANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHYLANTHRAQUINONE(6531-35-7)
• EPA Substance Registry System: 2,3-DIMETHYLANTHRAQUINONE(6531-35-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 6531-35-7(Hazardous Substances Data)

Usage

Uses

2,3-Dimethylanthraquinone may be used as starting reagent in the regioselective synthesis of 6-amino-2,3-anthracenedimethanol.

General Description

2,3-Dimethylanthraquinone is 2,3-dimethyl substituted anthraquinone and its synthesis has been reported. Electron transfer rate constants for the reaction between radical anions of 2,3-dimethylanthraquinone with benzyl bromide has been evaluated. The photoreactivity of 2,3-dimethylanthraquinone has been evaluated to investigate its usefulness as a photo-reagent for the analysis of ginsenosides using photoreduction fluorescence (PRF) detection method.

InChI:InChI=1/C16H12O2/c1-9-7-13-14(8-10(9)2)16(18)12-6-4-3-5-11(12)15(13)17/h3-8H,1-2H3

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 64-17-5 ethanol 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 58-27-5 menadione 
• 130-15-4 [1,4]naphthoquinone 
• 7664-93-9 sulfuric acid 
• 2159-42-4 2-(3,4-dimethylbenzoyl)benzoic acid 
• 79-24-3 Nitroethane 
• 31599-79-8 2-(chloromethyl)-3-methylnaphthalene-1,4-dione 
• 85-44-9 phthalic anhydride 
• 95-47-6 o-xylene 
• 412322-32-8 methyl 2-benzoyl-4,5-dimethylbenzoate 
• 93015-58-8 (+/-)-3.4-dimethyl-6t-benzoyl-cyclohexene-⁽³⁾-carboxylic acid-(1r) 
• 31581-11-0 2,3-bis(chloromethyl)-1,4-naphthoquinone 

Downstream Products

• 66552-77-0 2,3,9,10-Tetramethyl-anthracen 
• 613-06-9 2,3-dimethylanthracene 
• 1518979-42-4 2,3-dimethyl-2',2',2'-triphenyl-3'-(triphenylphosphanylidene)-10H-spiro[anthracene-9,4'-[1,2]oxaphosphetan]-10-one 
• 1518979-39-9 10-[2,4-bis(phenylimino)-3-(triphenylphosphanylidene)cyclobutylidene]-2,3-dimethylanthracen-9(10H)-one 
• 75348-22-0 2,3-dimethyl-1,4-di-p-toluidino-anthraquinone 
• 6705-73-3 9,10-anthraquinone-2,3-dicarboxylic anhydride 
• 10210-28-3 anthracene-2,3-dicarboxylic acid 
• 245326-55-0 2-Methyl-3-((Z)-styryl)-anthracene 
• 245326-44-7 2-bromomethyl-3-methylanthracene 
• 3225-89-6 1-amino-2,3-dimethyl-9,10-anthraquinone 
• 728028-60-2 2,3-dimethyl-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol 

Relevant articles and documents

Unexpected reactivity in naphthoquinone series

An unexpected reactivity of 2-chloromethyl-3-methyl-1,4-naphthoquinone 1 with primary nitroalkanes in classical SRN1 reaction conditions gives two series of new quinones: dialkyl anthraquinones and C-alkylated naphthoquinones.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

Synthesis of tetrafunctionalized pentiptycenequinones for construction of cyclic dimers with a cylindrical shape by boronate ester formation

Abstract New tetrasubstituted pentiptycenequinone derivatives 1 and 2 having two sets of diol moieties in a syn orientation were synthesized from the corresponding 2,3-disubstituted anthracene derivatives. The semicircular scaffold of these molecules is expected to be useful to create a belt-like structure having an aromatic π-wall. Indeed, the reaction of 1 with 1,4-phenylenediboronic acid or 4,4′-biphenyldiboronic acid quantitatively gave a 2:2 macrocyclic product via boronate ester formation. The efficient formation of these cyclic structures can be explained by favorable intramolecular cyclization at the final step.