3837-38-5

Usage

Uses

Used in Organic Synthesis:
2,6-Dimethylanthraquinone is used as an intermediate in the synthesis of various organic compounds. Its chemical structure allows it to be a versatile building block for creating a wide range of molecules with different functionalities and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-Dimethylanthraquinone is used as a key component in the development of new drugs. Its unique properties make it a promising candidate for the synthesis of novel therapeutic agents, potentially leading to the discovery of innovative treatments for various diseases.
Used in Dye Industry:
2,6-Dimethylanthraquinone is also utilized in the dye industry due to its yellow color. It can be used as a colorant in the production of various types of dyes and pigments, contributing to the development of new colorants with specific properties and applications.
Used in Chemical Research:
As a compound with distinct chemical properties, 2,6-Dimethylanthraquinone is employed in chemical research to study various reaction mechanisms and to develop new synthetic methods. Its use in research can lead to a better understanding of organic chemistry and the development of new techniques for compound synthesis.

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

Upstream product

• 19438-61-0 4-methylphthalic anhydride 
• 108-88-3 toluene 
• 33982-94-4 2,6-dimethyl-(4arH.8atH.9acH.10atH)-1,4,4a,5,8,8a,9a,10a-octahydro-anthraquinone 
• 56218-49-6 1-((1E,3E)-3,7-Dimethyl-octa-1,3,6-trienyl)-piperidine 
• 605-93-6 6-methyl-1,4-naphthoquinone 
• 7446-70-0 aluminium trichloride 
• 1711-06-4 3-Methylbenzoyl chloride 
• 7664-93-9 sulfuric acid 
• 22649-44-1 4-methyl-2-p-toluoyl-benzoic acid 
• 33982-94-4 bis-isoprene-quinone B 
• 33982-94-4 bis-isoprene-quinone B' 
• 64-19-7 acetic acid 
• 106-51-4 p-benzoquinone 
• 78-79-5 isoprene 

Downstream Products

• 635680-79-4 9,10-bis(p-cyanophenyl)-2,6-dimethylanthracene 
• 84-54-8 2-methylanthracene-9,10-dione 
• 138308-89-1 2,6-anthracene dicarboxylic acid 
• 635680-89-6 2,6-bis[(diethoxyphosphoryl)methyl]-9,10-bis(p-cyanophenyl)anthracene 
• 872034-34-9 9,10-bis(p-cyanophenyl)-2,6-bis(bromomethyl)anthracene 
• 863194-21-2 2,6-bis[(diethoxyphosphoryl)methyl]-9,10-diphenylanthracene 

Relevant academic research and scientific papers

Functionalization of Zirconium-Based Metal–Organic Layers with Tailored Pore Environments for Heterogeneous Catalysis

Intriguing properties and functions are expected to implant into metal–organic layers (MOLs) to achieve tailored pore environments and multiple functionalities owing to the synergies among multiple components. Herein, we demonstrate a facile one-pot synthetic strategy to incorporate multiple functionalities into stable zirconium MOLs via secondary ligand pillaring. Through the combination of Zr6-BTB (BTB=benzene-1,3,5-tribenzoate) layers and diverse secondary ligands (including ditopic and tetratopic linkers), 31 MOFs with multi-functionalities were systematically prepared. Notably, a metal–phthalocyanine fragment was successfully incorporated into this Zr-MOL system, giving rise to an ideal platform for the selective oxidation of anthracene. The organic functionalization of two-dimensional MOLs can generate tunable porous structures and environments, which may facilitate the excellent catalytic performance of as-synthesized materials.

Proton-Coupled Electron Transport in Anthraquinone-Based Zirconium Metal-Organic Frameworks

The ditopic ligands 2,6-dicarboxy-9,10-anthraquinone and 1,4-dicarboxy-9,10-anthraquinone were used to synthesize two new UiO-type metal-organic frameworks (MOFs; namely, 2,6-Zr-AQ-MOF and 1,4-Zr-AQ-MOF, respectively). The Pourbaix diagrams (E vs pH) of the MOFs and their ligands were constructed using cyclic voltammetry in aqueous buffered media. The MOFs exhibit chemical stability and undergo diverse electrochemical processes, where the number of electrons and protons transferred was tailored in a Nernstian manner by the pH of the media. Both the 2,6-Zr-AQ-MOF and its ligand reveal a similar electrochemical pKa value (7.56 and 7.35, respectively) for the transition between a two-electron, two-proton transfer (at pH a) and a two-electron, one-proton transfer (at pH > pKa). In contrast, the position of the quinone moiety with respect to the zirconium node, the effect of hydrogen bonding, and the amount of defects in 1,4-Zr-AQ-MOF lead to the transition from a two-electron, three-proton transfer to a two-electron, one-proton transfer. The pKa of this framework (5.18) is analogous to one of the three electrochemical pKa values displayed by its ligand (3.91, 5.46, and 8.80), which also showed intramolecular hydrogen bonding. The ability of the MOFs to tailor discrete numbers of protons and electrons suggests their application as charge carriers in electronic devices.

Efficient Synthesis of Anthraquinones from Diaryl Carboxylic Acids via Palladium(II)-Catalyzed and Visible Light-Mediated Transformations

Irradiation of 9-ester-substituted anthracenes with visible light results in the formation of endoperoxides in the absence of a photocatalyst, which further undergo base-assisted fragmentation to afford anthraquinones. The excited state species of anthracene generated by energy transfer, interacts with 3O2 to afford 1O2 by energy transfer and undergoes cycloaddition with 1O2. By employing palladium(II)-catalyzed and visible light-mediated transformations, we have developed an efficient synthetic protocol for accessing diverse anthraquinones from readily available diaryl carboxylic acids. The optimal result was obtained with palladium(II) acetate, Ac-Ile-OH, benzoquinone and potassium carbonate in tert-amyl alcohol under O2 at 90 °C with irradiation from a 30 W fluorescent light bulb. (Figure presented.).

Synthesis method of anthraquinone derivatives and tetracenedione derivatives through benzannulation reaction

The present invention relates to a method for synthesizing anthraquinone derivatives and tetracene dione derivatives through a benzannulation reaction, which presents a novel synthesis method, capable of processing synthesis easily, conveniently, and efficiently under mild conditions by an organic catalyst. The synthesis method uses an L-proline catalyst which is nontoxic, economical and easily available, compared to conventional production methods, thereby providing the anthraquinone derivatives and the tetracene dione derivatives through the one-pot benzannulation reaction of an α, β-unsaturated aldehyde compound, various 1,4-naphthoquinone compounds or 1,4-anthracenedione compounds. Various forms of anthraquinone derivatives or tetracene dione derivatives prepared by the synthesis method can be widely used for synthesis of natural products, dyes, and pharmaceutical products.COPYRIGHT KIPO 2017

Rigid Core Anthracene and Anthraquinone Linked Nitronyl and Iminoyl Nitroxide Biradicals

The first syntheses of bis(nitronyl nitroxide) and bis(iminoyl nitroxide) (diNN, diIN) biradicals linked through rigid acene core conjugating anthracene (A) and anthraquinone (AQ) units are reported. Computational modeling predicts weak intramolecular exchange in AQ-linked systems, but A-linked biradicals to have ground state multiplicities consistent with the Borden-Davidson disjointness model. Solution electron spin resonance spectra showed inter-radical exchange-coupled triplet states, except for 2,6-AQ biradicals showing isolated spin spectra. Crystallography of the A-linked biradicals shows a key role for inter-radical contacts for molecular packing. DiINs showed lower-dimensional dyad packing with disorder at the radical units: the conformationally more symmetrical diNNs gave staircase one-dimensional or brickwork two-dimensional lattices. Core anthracene unit stacking was only seen in two systems with bromine on the central anthracene ring: the (large) bromine occupies alternate side placement in dyad stacks for the diIN, chain stacks for the diNN. Magnetism of 2,7-A-linked systems showed predominant ferromagnetic intramolecular triplet-singlet splitting of 24-28 K for diNNs and 8 K for diINs, plus weak antiferromagnetic (AFM) interactions from intermolecular contacts. The 2,6-A-linked biradicals showed AFM exchange between spins. Both A and AQ cores offer possibilities for electronic material development, with a combination of multiple radical spins and π-electron-rich acene cores.

Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones

An efficient one-pot synthesis of anthraquinones and tetracenediones was achieved vial-proline catalyzed [4+2] cycloaddition of in situ generated azadiene from α,β-unsaturated aldehydes and 1,4-naphthoquinones or 1,4-anthracenedione in good to excellent yield. This protocol constitutes an unprecedented tandem benzannulation that allows one-pot construction of diverse anthraquinones and tetracenediones in the presence of organocatalysts. This methodology was applied successfully to the synthesis of naturally occurring molecules and photochemically interesting phenanthrenequinone derivatives.

Amide bond direction modulates G-quadruplex recognition and telomerase inhibition by 2,6 and 2,7 bis-substituted anthracenedione derivatives

G-quadruplex structures of DNA represent a potentially useful target for anticancer drugs. Stabilisation of this arrangement at the ends of chromosomes may inhibit the action of telomerase, an enzyme involved in immortalization of cancer cells. Appropriately substituted amido anthracenediones are effective G-quadruplex stabilizers, but no information is available as yet on the possible modulation of G-quadruplex recognition and telomerase inhibition produced by the direction of the amide bond. To understand the basis of amido anthracenedione selectivity, we have synthesized a number of derivatives bearing the -CO-NH- or -NH-CO- group linked to the planar anthraquinone (AQ) moiety at 2,6 and 2,7 positions. The various isomers were tested in terms of telomerase inhibition, determined by the TRAP assay, G-quadruplex stabilisation measured by the increase in melting temperature of the appropriately folded oligonucleotide using FRET, and conformational and G4 binding properties examined by molecular modelling techniques. In all cases, enzymatic inhibition and G-quadruplex stabilization were directly related, which strongly supports the proposed molecular mechanism of telomerase interference. Interestingly, the AQ-NH-CO- arrangement performs invariantly better than the AQ-CO-NH- arrangement, showing a clear preference among isomeric derivatives. Theoretical calculations suggest that the former amide arrangement is co-planar with the aromatic system, whereas the latter is tilted by about 30° when considering the most stable conformation. A more extended planar surface would allow more efficient stacking interactions with the quadruplex structure, hence more effective telomerase inhibition.

Remote aromatic stabilization in radical reactions

The rates of free radical reduction of a series of anthracene derivatives and 1-phenyl-4-bromodecane with tributyltin hydride are mediated by the remote aromatic substituent in an apparent through-space interaction. Density functional calculations suggest that this enhancement is not due to direct stabilization of the free radical intermediate, and is likely to be achieved through the interaction of the aromatic moiety with the polarized transition state leading to the intermediate.

High-performance organic semiconductors for thin-film transistors based on 2,6-bis(2-thienylvinyl)anthracene

We have synthesized two novel organic semiconductors, which have a symmetrically substituted thienylvinylene anthracene backbone. They show good electrical performances on SiO2/Si, with high field-effect mobilities of up to 0.4 cm2 V-1 s-1, and can easily be synthesized in large quantities. In addition, the high mobility of such semiconductors can be achieved at low substrate deposition temperatures. The Royal Society of Chemistry.