5,8-Dimethoxy-3-methylnaphthalen-1-ol

Base Information

• Chemical Name: 5,8-Dimethoxy-3-methylnaphthalen-1-ol
• CAS No.: 50559-08-5
• Molecular Formula: C13H14O3
• Molecular Weight: 218.252
• ChEMBL ID: CHEMBL2071229
• DSSTox Substance ID: DTXSID50481628
• Metabolomics Workbench ID: 126690
• Nikkaji Number: J598.061E
• Wikidata: Q82317136
• Mol file: 50559-08-5.mol

Synonyms:5,8-dimethoxy-3-methylnaphthalen-1-ol;50559-08-5;1-Naphthalenol, 5,8-dimethoxy-3-methyl-;CHEMBL2071229;DTXSID50481628;5,8-dimethoxy-3-methyl-1-naphthol

Chemical Property of 5,8-Dimethoxy-3-methylnaphthalen-1-ol

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 218.094294304
• Heavy Atom Count: 16
• Complexity: 231

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2=C(C=CC(=C2C(=C1)O)OC)OC

Technology Process of 5,8-Dimethoxy-3-methylnaphthalen-1-ol

There total 1 articles about 5,8-Dimethoxy-3-methylnaphthalen-1-ol 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:

Triisopropyl borate (5419-55-6) + 2-bromo-5,8-dimethoxy-3-methylnaphthalen-1-ol (101459-25-0) → 5,8-dimethoxy-3-methylnaphthalen-1-ol (50559-08-5) + C13H15BO5 + 5,8-dimethoxy-3-methyl-1,2-naphthaquinone (86432-51-1)

Guidance literature:

2-bromo-5,8-dimethoxy-3-methylnaphthalen-1-ol; With n-butyllithium; In tetrahydrofuran; at -35 - -20 ℃; for 0.166667h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; at -35 - -20 ℃; Inert atmosphere;

With water; In tetrahydrofuran; at -20 ℃; Temperature; Solvent; Acidic conditions; Inert atmosphere;

DOI:10.1021/acs.jnatprod.0c00800

Reference yield: 95.0%

5,8-dimethoxy-3-methylnaphthalen-1-ol (50559-08-5) + benzyl bromide (100-39-0) → 1-(benzyloxy)-5,8-dimethoxy-3-methylnaphthalene (89475-21-8)

Guidance literature:

With sodium hydride; potassium iodide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1080/14786419.2020.1761356

Reference yield:

5,8-dimethoxy-3-methylnaphthalen-1-ol (50559-08-5) → 2-bromo-8-hydroxy-6-methyl-1,4-naphthoquinone (161811-59-2) + 2-bromo-5-hydroxy-7-methyl-1,4-naphthoquinone (273200-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine hydrochloride / 0.5 h / Reflux

1.2: 0.67 h / 20 °C

2.1: bromine / acetic acid / 0.42 h / 20 °C / Darkness; Inert atmosphere

With bromine; pyridine hydrochloride; In acetic acid;

DOI:10.1021/acs.jnatprod.0c00800

upstream raw materials:

Triisopropyl borate

2-bromo-5,8-dimethoxy-3-methylnaphthalen-1-ol

Downstream raw materials:

Stypandron

1-(benzyloxy)-5,8-dimethoxy-3-methylnaphthalene

2-bromo-8-hydroxy-6-methyl-1,4-naphthoquinone

2-bromo-5-hydroxy-7-methyl-1,4-naphthoquinone