483-54-5

Basic information

• Product Name: 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE
• Synonyms: 2,3-DIMETHOXY-5,6-DIMETHYL-2,5-CYCLOHEXADIENE-1,4-DIONE;2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE;AURANTIOGLIOCLADIN;2,3-Dimethoxy-5,6-dimethyl-1,4-benzoquinone
• CAS NO: 483-54-5
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• Product Categories: Anthraquinones, Hydroquinones and Quinones
• Mol File: 483-54-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 62.5°
• Boiling Point: 337.326°C at 760 mmHg
• Flash Point: 150.393°C
• Appearance: /
• Density: 1.167g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE(483-54-5)
• EPA Substance Registry System: 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE(483-54-5)

Safety Data

• Hazardous Substances Data: 483-54-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE is used as a reagent in organic synthesis for its versatile chemical properties, enabling the production of various compounds and intermediates.
Used in Pharmaceutical and Fine Chemical Production:
As a precursor, 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE is utilized in the manufacturing process of pharmaceuticals and fine chemicals, contributing to the development of new and improved products.
Used in Antioxidant Applications:
Leveraging its antioxidant properties, 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE is employed in the development of new drugs and materials, offering potential health benefits and enhancing the stability and performance of various products.
Used in Medical Research:
Due to its unique chemical structure and biological activity, 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE is studied for its potential use in the treatment of certain medical conditions, opening avenues for novel therapeutic approaches.

InChI:InChI=1/C10H12O4/c1-5-6(2)8(12)10(14-4)9(13-3)7(5)11/h1-4H3

Upstream product

• 776-33-0 1,4-dihydroxy-2,3-dimethoxy-5,6-dimethylbenzene 
• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 75-65-0 tert-butyl alcohol 
• 614-45-9 tert-Butyl peroxybenzoate 
• 64-19-7 acetic acid 
• 22028-13-3 4-Benzyloxy-3-methoxy-2,5-dinitro-benzaldehyd-dimethylacetal 
• 22028-12-2 4-Benzyloxy-3-methoxy-2,5-dinitro-benzaldehyd 
• 22028-10-0 4-Dichlormethyl-2-methoxy-3,6-dinitrophenol 
• 22028-11-1 4-Hydroxymethyl-2-methoxy-3,6-dinitro-phenol 
• 2446-67-5 2-Hydroxy-3-methoxy-5-methyl-p-benzochinon 
• 22028-03-1 2,5-Dinitro-vanillin-dimethylacetal 
• 2450-26-2 2-nitrovanillin 
• 22028-02-0 3,4-Dimethoxy-2,5-dinitro-benzaldehyd 
• 2698-73-9 4-Hydroxy-3-methoxy-2,5-dinitro-benzaldehyd 

Downstream Products

• 87810-96-6 C₁₀H₁₂O₄^(2-) 
• 102787-01-9 1,2,3,4-tetramethoxy-5,6-dimethyl-benzene 
• 100118-71-6 tetramethoxy-phthalic acid 
• 39154-47-7 tetramethoxy-phthalic acid anhydride 
• 776-33-0 1,4-dihydroxy-2,3-dimethoxy-5,6-dimethylbenzene 

Relevant articles and documents

Iron-Catalyzed Radical Methylation of Activated Alkenes with tert -Butanol as the Methyl Source

A free-radical-initiated methylation/addition/cyclization of N -arylacrylamides and a methylation/addition/elimination of quinines have been developed in which t -BuOH is used as a methyl source. These reactions provide effective and selective methods for the synthesis of various methylated oxindoles and quinones in moderate to good yields.

Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant

A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone. Notably, antimalarial parvaquone was synthesized by the reaction.

In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues

Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV-vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure-activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4′-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 μM and 6.2 μM. This would make them as valuable candidates for future pharmacological studies.

Rearrangements of cyclobutenones. Synthesis of benzoquinones from 4-alkenyl-4-hydroxycyclobutenones

The rearrangement of 4-alkenyl-4-hydroxycyclobutenones to quinones and related aromatic compounds is described. This rearrangement is complimentary to the previously reported ring expansions of 4-aryl- and 4-alkynyl-4-hydroxycyclobutenones. The synthetic scope and utility of the reaction are discussed. It is employed as a key step in the synthesis of a number of benzoquinones as well as in the total synthesis of the natural product, (±)-O-methylperezone and its regioisomer, (±)-O-methylisoperezone as well as coenzyme Q0 and aurantiogliocladin.