5-Hydroxy-2,3-dimethyl-1,4-naphthoquinone

Base Information

• Chemical Name: 5-Hydroxy-2,3-dimethyl-1,4-naphthoquinone
• CAS No.: 80596-51-6
• Molecular Formula: C12H10O3
• Molecular Weight: 202.21
• DSSTox Substance ID: DTXSID001272658
• Nikkaji Number: J657.697D
• Wikidata: Q105300891
• Metabolomics Workbench ID: 46636
• Mol file: 80596-51-6.mol

Synonyms:5-Hydroxy-2,3-dimethyl-1,4-naphthoquinone;3-Methylplumbagin;80596-51-6;2,3-Dimethylplumbagin;SCHEMBL5793791;CHEBI:173556;DTXSID001272658;5-hydroxy-2,3-dimethyl-[1,4]naphthoquinone;5-HYDROXY-2,3-DIMETHYLNAPHTHALENE-1,4-DIONE;5-hydroxy-2,3-dimethyl-1,4-dihydronaphthalene-1,4-dione

Chemical Property of 5-Hydroxy-2,3-dimethyl-1,4-naphthoquinone

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 202.062994177
• Heavy Atom Count: 15
• Complexity: 354

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)C

Technology Process of 5-Hydroxy-2,3-dimethyl-1,4-naphthoquinone

There total 2 articles about 5-Hydroxy-2,3-dimethyl-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: 60.0%

2-hydroxynaphtho-1,4-quinone (83-72-7) + dimethyl sulfoxide (67-68-5,8070-53-9) → menadione (58-27-5,34524-96-4) + 2,3-dimethyl-5-hydroxy-1,4-naphthoquinone (80596-51-6)

Guidance literature:

With copper(II) sulfate; at 50 ℃; for 2h;

DOI:10.1080/00397919508015851

Reference yield:

5-hydroxynaphtho-1,4-quinone (481-39-0) + acetic acid (64-19-7,77671-22-8) → 5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5) + isoplumbagin (14777-17-4) + 2,3-dimethyl-5-hydroxy-1,4-naphthoquinone (80596-51-6)

Guidance literature:

With ammonium peroxydisulfate; silver nitrate; Multistep reaction; 1.) Acetonitril, 80 deg C, 2.) H₂O, Rueckfluss, 2 h;

DOI:10.1002/ardp.19843170316

Reference yield: 52.3%

phenyllithium (591-51-5) + 2,3-dimethyl-5-hydroxy-1,4-naphthoquinone (80596-51-6) → 4,8-dihydroxy-2,3-dimethyl-4-phenyl-1(4H)-naphthalenone + trans-2,3-dimethyl-1,4-diphenyl-1,4-dihydronaphthalen-1,4,5-triol + cis-2,3-dimethyl-1,4-diphenyl-1,4-dihydronaphthalen-1,4,5-triol

Guidance literature:

In tetrahydrofuran; cyclohexane; at 0 ℃; for 0.5h;

DOI:10.1248/cpb.47.209

upstream raw materials:

5-hydroxynaphtho-1,4-quinone

acetic acid

2-hydroxynaphtho-1,4-quinone

dimethyl sulfoxide