5,8-Dihydroxy-2,7-dimethoxy-1,4-naphthoquinone

Base Information

• Chemical Name: 5,8-Dihydroxy-2,7-dimethoxy-1,4-naphthoquinone
• CAS No.: 2808-46-0
• Molecular Formula: C12H10 O6
• Molecular Weight: 250.2
• NSC Number: 305977
• UNII: ON61OGA286
• DSSTox Substance ID: DTXSID20182357
• Nikkaji Number: J61.695H
• Wikidata: Q83053019
• Metabolomics Workbench ID: 100554
• Mol file: 2808-46-0.mol

Synonyms:Spinochrome M;5,8-Dihydroxy-2,7-dimethoxy-1,4-naphthoquinone;2808-46-0;1,4-NAPHTHOQUINONE, 5,8-DIHYDROXY-2,7-DIMETHOXY-;1,4-Naphthalenedione, 5,8-dihydroxy-2,7-dimethoxy-;NSC 305977;BRN 1981899;NAPHTHOQUINONE, 5,8-DIHYDROXY-2,7-DIMETHOXY;ON61OGA286;NSC-305977;5,8-dihydroxy-2,7-dimethoxynaphthalene-1,4-dione;NSC305977;UNII-ON61OGA286;DTXSID20182357;1, 5,8-dihydroxy-2,7-dimethoxy-;LS-95638;5,8-Dihydroxy-2,7-dimethoxynaphthoquinone #;NAPHTHOQUINONE,8-DIHYDROXY-2,7-DIMETHOXY;5,8-DIHYDROXY-2,7-DIMETHOXY-1,4-NAPHTHALENEDIONE

Chemical Property of 5,8-Dihydroxy-2,7-dimethoxy-1,4-naphthoquinone

Chemical Property:

• Vapor Pressure: 4.9E-14mmHg at 25°C
• Melting Point: 235-236 °C
• Boiling Point: 579.7°Cat760mmHg
• PKA: 6.71±0.20(Predicted)
• Flash Point: 231.4°C
• PSA: 93.06000
• Density: 1.53g/cm³
• LogP: 1.01570
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 250.04773803
• Heavy Atom Count: 18
• Complexity: 401

Purity/Quality:

99% ^*data from raw suppliers

5,8-DIHYDROXY-2,7-DIMETHOXY-1,4-NAPHTHOQUINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=O)C2=C(C1=O)C(=C(C=C2O)OC)O

Technology Process of 5,8-Dihydroxy-2,7-dimethoxy-1,4-naphthoquinone

There total 7 articles about 5,8-Dihydroxy-2,7-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: 70.0%

Trimethyl orthoacetate (1445-45-0) + 2,5,7,8-tetrahydroxynaphthalene-1,4-dione (2473-16-7) → 2,7-Dimethoxy-naphthazarin (2808-46-0) + 2,5,8-trihydroxy-7-methoxy-1,4-naphthoquinone (3404-93-1)

Guidance literature:

at 109 ℃; for 1.5h;

DOI:10.1007/s11172-019-2415-5

Reference yield: 35.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 2,5,7,8-tetrahydroxynaphthalene-1,4-dione (2473-16-7) → 2,7-Dimethoxy-naphthazarin (2808-46-0) + 2,5,8-trihydroxy-7-methoxy-1,4-naphthoquinone (3404-93-1)

Guidance literature:

In diethyl ether;

DOI:10.1023/A:1009533403588 DOI:10.1016/S0040-4020(02)00060-1

Reference yield:

3,6,8-trimethoxy-1-naphthol (13586-04-4) → 2,7-Dimethoxy-naphthazarin (2808-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1: MgI₂ / diethyl ether

2: (KO₃S)2NO

3: (CF₃CO)2O, aq. H₂O₂

With potassium nitrososulfonate; dihydrogen peroxide; trifluoroacetic anhydride; magnesium iodide; In diethyl ether;

DOI:10.1039/c19680000071

upstream raw materials:

5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone

diazomethane

2,5,7,8-tetrahydroxynaphthalene-1,4-dione

3,6,8-trimethoxy-1-naphthol

Refernces

• 1、 Natori,Kumada,Nishikawa. "The structure of mompain, a naphthoquinone from Helicobasidium mompa Tanaka, and its relation to spinochrome A (M).". . p. 633 - 635. Retrieved 1965.
• 2、 Balaneva,Shestak,Novikov. "Trimethyl orthoacetate as a convenient reagent for selective methylation of β-OH groups of (poly)hydroxynaphthazarins". . p. 55 - 63. Retrieved 2019/04/25.
• 3、 Glazunov,Tchizhova,Shestak,Sopel'nyak,Anufriev. "Chemistry of naphthazarin derivatives 8. Determination of structures of substituted 2-hydroxy-6(7)-methoxynaphthazarins and 7(8)-hydroxypyranonaphthazarins by IR spectroscopy". . p. 95 - 100. Retrieved 2007/10/03.