21086-65-7

Basic information

• Product Name: 4,5-DIMETHOXY-1,2-BENZOQUINONE
• Synonyms: 4,5-DIMETHOXY-O-BENZOQUINONE;NSC121600;4,5-Dimethoxy-3,5-cyclohexadiene-1,2-dione;4,5-DIMETHOXY-1,2-BENZOQUINONE
• CAS NO: 21086-65-7
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• EINECS: 244-205-5
• Product Categories: Anthraquinones, Hydroquinones and Quinones
• Mol File: 21086-65-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 226-230°C
• Boiling Point: 324.3 °C at 760 mmHg
• Flash Point: 146.2 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 0.000247mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: 4,5-DIMETHOXY-1,2-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIMETHOXY-1,2-BENZOQUINONE(21086-65-7)
• EPA Substance Registry System: 4,5-DIMETHOXY-1,2-BENZOQUINONE(21086-65-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 21086-65-7(Hazardous Substances Data)

Usage

Description

4,5-DIMETHOXY-1,2-BENZOQUINONE, also known as 2,5-Dimethoxy-1,4-benzoquinone, is a quinone derivative with the molecular formula C8H8O4. It is a chemical compound known for its antioxidant and antitumor properties, and has been studied for its potential use in various therapeutic applications.

Uses

Used in Cancer Treatment:
4,5-DIMETHOXY-1,2-BENZOQUINONE is used as a potential therapeutic agent for cancer treatment due to its antitumor properties. It has been studied for its potential to target and inhibit the growth of cancer cells, making it a promising candidate for further research and development in oncology.
Used in Neurodegenerative Disease Therapy:
4,5-DIMETHOXY-1,2-BENZOQUINONE is used as a potential therapeutic agent for neurodegenerative diseases. Its antioxidant properties may help protect neurons from oxidative stress and damage, which are common features of neurodegenerative conditions such as Alzheimer's and Parkinson's diseases.
Used in Antimicrobial Applications:
4,5-DIMETHOXY-1,2-BENZOQUINONE is used as a potential antimicrobial agent due to its ability to inhibit the growth of certain bacteria and other microorganisms. This property makes it a candidate for further research in the development of new antimicrobial drugs and treatments.
Used in Antiviral Applications:
4,5-DIMETHOXY-1,2-BENZOQUINONE has been investigated for its potential antiviral properties. Its ability to inhibit viral replication and infectivity may contribute to the development of new antiviral therapies and treatments for various viral infections.
Used in Organic Synthesis:
4,5-DIMETHOXY-1,2-BENZOQUINONE is used as a reagent in organic synthesis reactions. Its unique chemical structure and properties make it a valuable component in the synthesis of various organic compounds and materials, contributing to the advancement of organic chemistry and related fields.

InChI:InChI=1/C8H8O4/c1-11-7-3-5(9)6(10)4-8(7)12-2/h3-4H,1-2H3

Upstream product

• 67-56-1 methanol 
• 120-80-9 benzene-1,2-diol 
• 99814-64-9 4-methoxy-5-(4-methoxyphenoxy)cyclohexa-3,5-diene-1,2-dione 
• 598-32-3 2-hydroxy-3-butene 
• 91-16-7 1,2-dimethoxybenzene 
• 546-67-8 lead(IV) tetraacetate 
• 2033-89-8 3,4-dimethoxyphenol 
• 3391-86-4 1-octen-3-ol 
• 2441-46-5 1,2,4,5-tetramethoxybenzene 
• 115320-11-1 6-<(dimethylamino)methyl>-3,4-dimethoxyphenol 
• 103951-59-3 1-(3,4-Dimethoxyphenyl)-2-phenylpropanol 
• 115060-94-1 2-Hydroxy-4,5-dimethoxybenzyl alcohol 
• 75080-64-7 5,6-dimethoxyspiro<1,3-benzodioxole-2,1'-cyclohexane> 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 

Downstream Products

• 58256-24-9 4,5-diaziridinyl-1,2-benzoquinone 
• 109765-47-1 3-chloro-2-hydroxy-4,4,5-trimethoxy-2,5-cyclohexadien-1-one 
• 109765-48-2 2,5-dichloro-6-hydroxy-3,3,4,4-tetramethoxy-5-cyclohexen-1-one 
• 82511-16-8 6-(3-Diethylamino-prop-1-ynyl)-6-hydroxy-3,4-dimethoxy-cyclohexa-2,4-dienone 
• 82511-10-2 6-<3-(benzyloxy)-1-propynyl>-3,4-dimethoxy-6-hydroxy-2,4-cyclohexadienone 
• 90433-59-3 4,5-Dimethoxy-2-(vinyloxy)phenol 
• 90433-66-2 4,5-Dimethoxy-2-phenoxyphenol 
• 1664-27-3 1,2-dihydroxy-4,5-dimethoxybenzene 
• 53250-42-3 4-(4-methylphenylamino)-5-methoxy-1,2-benzoquinone 
• 62439-38-7 4-(4-chlorophenylamino)-5-methoxy-1,2-benzoquinone 
• 72106-98-0 4-(4-methoxyphenylamino)-5-methoxy-1,2-benzoquinone 
• 108213-69-0 1,2-bis(phenylethynyl)-4,5-dimethoxy-3,5-cyclohexadiene-1,2-diol 
• 82521-45-7 3,4-dimethoxy-6-hexynyl-6-hydroxy-2,4-cyclohexadienone 
• 108213-95-2 4,5-dimethoxy-1-hexynyl-2-methyl-3,5-cyclohexadiene-1,2-diol 

Relevant articles and documents

Synthesis of 4, 5-Dimethoxy-o-benzoquinone by formal [4+2] cyclization of 2, 3-dimethoxy-1, 3-butadiene with oxalyl chloride

The cyclization of 2, 3-dimethoxy-1, 3-butadiene with oxalyl chloride provides a new method for the synthesis of 4, 5-dimethoxy-o-benzoquinone. 2009. Bentham Science Publishers Ltd.

Synthesis, structure, and reactivity of [Cu(phen)2]ClO 2: Aerobic oxidation of Cl- to ClO2- at room temperature

An unusual 4e- oxidation of Cl- into ClO 2- occurred during the reaction between CuCl and phenanthroline (phen) in air to form a [Cu(phen)2]ClO2 complex, which is capable of oxidizing catechol into the highly substituted pentenone derivative methyl 1-hydroxy-2-oxo-4,5,5-trimethoxycyclopent-3-ene-1- carboxylate through contraction of the aromatic ring by extradiol C-C bond cleavage concomitant with the further formation of a C-C bond. Copyright

Total synthesis and biological evaluation of the nakijiquinones

The Her-2/Neu receptor tyrosine kinase is vastly overexpressed in about 30% of primary breast, ovary, and gastric carcinomas. The nakijiquinones are the only naturally occurring inhibitors of this important oncogene, and structural analogues of the nakijiquinones may display inhibitory properties toward other receptor tyrosine kinases involved in cell signaling and proliferation. Here, we describe the first enantioselective synthesis of the nakijiquinones. Key elements of the synthesis are (i) the reductive alkylation of a Wieland - Mieschertype enone with a tetramethoxyaryl bromide, (ii) the oxidative conversion of the aryl ring into a p-quinoid system, (iii) the regioselective saponification of one of the two vinylogous esters incorporated therein, and (iv) the selective introduction of different amino acids via nucleophilic conversion of the remaining vinylogous ester into the corresponding vinylogous amide. The correct stereochemistry and substitution patterns are completed by conversion of two keto groups into a methyl group and an endocyclic olefin via olefination/reduction and olefination/isomerization sequences, respectively. This synthesis route also gave access to analogues of nakijiquinone C with inverted configuration at C-2 or with an exocyclic instead of an endocyclic double bond. Investigation of the kinase-inhibiting properties of the synthesized derivatives revealed that the C-2 epimer 30 of nakijiquinone C is a potent and selective inhibitor of the KDR receptor, a receptor tyrosine kinase involved in tumor angiogenesis. Molecular modeling studies based on the crystal structure of KDR and a model of the ATP binding site built from a crystal structure of FGF-R revealed an insight into the structural basis for the difference in activity between the natural product nakijiquinone C and the C-2 epimer 30.