22506-55-4

Basic information

• Product Name: 2,3-DIMETHOXYANTHRAQUINONE
• Synonyms: 2,3-DIMETHOXYANTHRAQUINONE;2,3-Dimethoxy-9,10-anthraquinone;2,3-dimethoxyanthracene-9,10-dione
• CAS NO: 22506-55-4
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26408
• Mol File: 22506-55-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 231-233 °C
• Boiling Point: 462.1°C at 760 mmHg
• Flash Point: 207.9°C
• Appearance: /
• Density: 1.295g/cm³
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 2,3-DIMETHOXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHOXYANTHRAQUINONE(22506-55-4)
• EPA Substance Registry System: 2,3-DIMETHOXYANTHRAQUINONE(22506-55-4)

Safety Data

• Hazardous Substances Data: 22506-55-4(Hazardous Substances Data)

Usage

General Description

2,3-Dimethoxyanthraquinone is a chemical compound with the molecular formula C16H12O4. It is an anthraquinone derivative with two methoxy groups attached to the 2 and 3 positions of the anthraquinone skeleton. 2,3-DIMETHOXYANTHRAQUINONE is commonly used as a dye intermediate for the production of various colorants and pigments, due to its ability to impart bright and vibrant colors. It is also used as a building block in the synthesis of pharmaceuticals and organic compounds. Additionally, 2,3-Dimethoxyanthraquinone is known for its antioxidant and anti-inflammatory properties, making it a potential candidate for the development of new therapeutic treatments. However, it is important to handle and use this chemical with caution, as it can be harmful if ingested or inhaled, and may cause skin and eye irritation upon contact.

InChI:InChI=1/C16H12O4/c1-19-13-7-11-12(8-14(13)20-2)16(18)10-6-4-3-5-9(10)15(11)17/h3-8H,1-2H3

Upstream product

• 74-83-9 methyl bromide 
• 483-35-2 hystazarin 
• 91-16-7 1,2-dimethoxybenzene 
• 24388-70-3 1,3-dimethoxy-1,3-dihydroisobenzofuran 
• 17777-02-5 (3,4-dimethoxyphenyl)phenylacetic acid 
• 140-88-5 ethyl acrylate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 101597-68-6 methyl 2-(3,4-dimethoxybenzoyl)benzoate 
• 222633-66-1 methyl 4-(3,4-dimethoxyphenyl)-4-oxobut-2-ynoate 
• 3588-31-6 2,3-dimethoxy-1,3-butadiene 
• 78239-04-0 (2-bromo-4,5-dimethoxyphenyl)phenylmethane 
• 59142-62-0 (2-bromo-4,5-dimethoxyphenyl)phenylmethanol 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 134589-26-7 2,3-bis-n-decyloxyanthracene 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 

Relevant articles and documents

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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.

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 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.