6531-35-7

Usage

Uses

Used in Chemical Synthesis Industry:
2,3-Dimethylanthraquinone is used as a starting reagent for the regioselective synthesis of 6-amino-2,3-anthracenedimethanol. This synthesis process is crucial for the production of specific chemical compounds and pharmaceuticals that require the unique structural features provided by 2,3-dimethylanthraquinone as a precursor.

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

• 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) 
• 130-15-4 [1,4]naphthoquinone 
• 31581-11-0 2,3-bis(chloromethyl)-1,4-naphthoquinone 
• 684262-77-9 2,3-dimethyl-1,4,5,8-tetrahydro-anthraquinone 
• 471241-97-1 2,3-dimethyl-9,10-dihydroanthracene 
• 7664-93-9 sulfuric acid 
• 2159-42-4 2-(3,4-dimethylbenzoyl)benzoic acid 
• 55538-11-9 1,4,4a,9a-tetrahydro-2,3-dimethylanthracene-9,10-dione 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 2670-23-7 2,3-dimethyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione 
• 79-24-3 Nitroethane 

Downstream Products

• 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 
• 245326-55-0 2-Methyl-3-((Z)-styryl)-anthracene 
• 245326-44-7 2-bromomethyl-3-methylanthracene 
• 613-06-9 2,3-dimethylanthracene 
• 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 
• 66552-77-0 2,3,9,10-Tetramethyl-anthracen 
• 10210-28-3 anthracene-2,3-dicarboxylic acid 
• 75348-22-0 2,3-dimethyl-1,4-di-p-toluidino-anthraquinone 
• 6705-73-3 9,10-anthraquinone-2,3-dicarboxylic anhydride 

Relevant academic research and scientific papers

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.

Compression of a Flapping Mechanophore Accompanied by Thermal Void Collapse in a Crystalline Phase

Mechanical control of the molecular energy landscape is an important issue in modern materials science. Mechanophores play a unique role in that the mechanical responses are induced against the activation barrier for intramolecular transformation with the aid of external forces. Here we report an unprecedented activation process of a flexible flapping mechanophore. Namely, thermal void collapse in a crystalline phase triggers mechanophore compression in a definite proportion. Unfavored conformational planarization of the flapping mechanophore is compulsorily induced by packing force, leading to a total energy gain in crystal packing. Fluorescence chromism indicates extended π conjugation resulting from the mechanophore compression, giving rise to an energy transfer from the unpressed to compressed conformers.

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.

A Ni-Mg-Al layered triple hydroxide-supported Pd catalyst for heterogeneous acceptorless dehydrogenative aromatization

In the presence of a Ni-Mg-Al layered triple hydroxide-supported Pd catalyst, the acceptorless dehydrogenative aromatization of a wide range of cyclohexanols/cyclohexanones and cyclohexylamines efficiently proceeded to give the corresponding phenols and anilines, respectively, in moderate to high yields with the liberation of molecular hydrogen.

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.

Synthesis of fluorenone and anthraquinone derivatives from aryl- and aroyl-substituted propiolates

Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Diels-Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.

Metal-free activation of C-C multiple bonds through halide ion pairs: Diels-Alder reactions with subsequent aromatization

Imidazolium and ammonium halides, both in homogeneous phase or immobilized on mesoporous silica, proved able to promote the aromatization reaction of Diels-Alder adducts under ethylene and H2 elimination. These observations point to the increased nucleophilicity of such halide ions. They also open the possibility to employ such ion pairs as nucleophilic organocatalysts, for example, as substitutes for phosphines or amines.

Formation of arenes via diallylarenes: Strategic utilization of Suzuki-Miyaura cross-coupling, Claisen rearrangement and ring-closing metathesis

Two new synthetic strategies for benzoannulation are reported. The first strategy is based on the Suzuki-Miyaura cross-coupling reaction. To this end, various ortho-diallylbenzene derivatives were prepared from the corrresponding diiodo derivatives by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were subjected to a ring-closing metathesis (RCM) and one-pot dichlorodicyanoquinone (DDQ) oxidation sequence to deliver 2-substituted naphthalenes. In the second strategy, a double Claisen rearrangement and RCM protocol have been used as key steps to give highly functionalized benzoannulated quinone derivatives.

Nitrous oxide oxidation catalyzed by ruthenium porphyrin complex

Dinitrogen oxide was employed as a clean oxidant for various oxidations in the presence of a catalytic amount of dioxoruthenium tetramesitylporphyrin complex (Ru(tmp)(O)2). A variety of olefins, secondary alcohols, and benzyl alcohols were smoothly oxidized to the corresponding epoxides, ketones, and aldehydes in high yields. In the oxidation of 9,10-dihydroanthracene derivatives, the competitive reactions affording anthraquinones and anthracenes could be regulated by the reaction conditions. At a high temperature (200°C), anthraquinones were selectively produced, while the anthracenes were selectively produced by the addition of sulfuric acid.

Oxidative dehydrogenation and the aromatization of polycycles using o-iodoxybenzoic acid (IBX)

An efficient and convenient method for the dehydrogenation and aromatization of various polycycles using o-iodoxybenzoic acid (IBX) is described.