2,3-Dimethoxy-1,4-naphthoquinone

Base Information

• Chemical Name: 2,3-Dimethoxy-1,4-naphthoquinone
• CAS No.: 6956-96-3
• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.209
• Hs Code.: 2914690090
• European Community (EC) Number: 636-211-5
• NSC Number: 69355
• UNII: MFW94A3JEK
• DSSTox Substance ID: DTXSID8040935
• Nikkaji Number: J394.327E
• Wikidata: Q27133127
• Metabolomics Workbench ID: 63242
• ChEMBL ID: CHEMBL402468
• Mol file: 6956-96-3.mol

Synonyms:2,3-dimethoxy-1,4-naphthoquinone;DMNQ

Chemical Property of 2,3-Dimethoxy-1,4-naphthoquinone

Chemical Property:

• Vapor Pressure: 2.28E-06mmHg at 25°C
• Boiling Point: 392.5°C at 760 mmHg
• Flash Point: 177.6°C
• PSA: 52.60000
• Density: 1.28g/cm³
• LogP: 1.57000
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml) or in Ethanol (up to 5 mg/ml).
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 218.05790880
• Heavy Atom Count: 16
• Complexity: 322

Purity/Quality:

98%,99%, ^*data from raw suppliers

DMNQ ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=O)C2=CC=CC=C2C1=O)OC
• Description: DMNQ is a 1,4-naphthoquinone that acts as a redox-cycling agent, typically increasing intracellular superoxide and hydrogen peroxide formation. The amount of oxidative stress is proportional to the amount of DMNQ applied and can alter diverse cellular parameters, including signal transduction, mitochondrial function, and gene expression.
• Uses: DMNQ is a non-alkylating redox cycling quinone. 2,3-Dimethoxy-1,4-naphthoquinone has been used to investigate the effects of ethanol on podocyte apoptosis under hypoxic and hyperoxic conditions.

Technology Process of 2,3-Dimethoxy-1,4-naphthoquinone

There total 17 articles about 2,3-Dimethoxy-1,4-naphthoquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + methanol (67-56-1) → 2,3-dimethoxy-1,4-naphthoquinone (6956-96-3)

Guidance literature:

With sodium methylate; for 6h; Heating; Inert atmosphere;

DOI:10.1016/j.electacta.2022.139889

Reference yield: 73.0%

2,3-dimethoxy-4-hydroxy-4-phenyl-2-cyclobuten-1-one (98122-97-5) → 2,3-dimethoxy-1,4-naphthoquinone (6956-96-3)

Guidance literature:

With silica gel; Product distribution; Mechanism; var. oxidation conditions; other cyclobutenones;

DOI:10.1021/jo00240a011

Reference yield: 72.7%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + sodium methylate (124-41-4) → 2,3-dimethoxy-1,4-naphthoquinone (6956-96-3)

Guidance literature:

In methanol; for 6h; Reflux;

DOI:10.3390/molecules18021973

upstream raw materials:

diazomethane

isonaphthazarine

2,3-Dichloro-1,4-naphthoquinone

sodium methylate

Downstream raw materials:

2-bis(4-tert-butylbenzoyl)amino-3-methoxy-1,4-naphthoquinone

2-bis(4-fluorobenzoyl)amino-3-methoxy-1,4-naphthoquinone

2-bis(4-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone

2-bis(3-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone

Refernces

• 1、 Chrastina, Adrian,Welsh, John,Rondeau, Gaelle,Abedinpour, Parisa,Borgstr?m, Per,Baron, Véronique T.. "Plumbagin-Serum Albumin Interaction: Spectral, Electrochemical, Structure-Binding Analysis, Antiproliferative and Cell Signaling Aspects with Implications for Anticancer Therapy". . p. 1338 - 1347. Retrieved 2020.
• 2、 Dias, Gleiston G.,Rogge, Torben,Kuniyil, Rositha,Jacob, Claus,Menna-Barreto, Rubem F. S.,Da Silva Júnior, Eufranio N.,Ackermann, Lutz. "Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents". supporting information. p. 12840 - 12843. Retrieved 2018/11/30.