2-Iodo-3-methoxynaphthalene

Base Information

• Chemical Name: 2-Iodo-3-methoxynaphthalene
• CAS No.: 795278-91-0
• Molecular Formula: C₁₁H₉IO
• Molecular Weight: 284.096
• DSSTox Substance ID: DTXSID90704787
• Wikidata: Q82637337
• Mol file: 795278-91-0.mol

Synonyms:2-Iodo-3-methoxynaphthalene;795278-91-0;SCHEMBL18023050;DTXSID90704787;MFCD17012575;CS-0191415;FT-0725984;E91330

Chemical Property of 2-Iodo-3-methoxynaphthalene

Chemical Property:

• PSA: 9.23000
• LogP: 3.45300
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 283.96981
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

97% ^*data from raw suppliers

2-Iodo-3-methoxynaphthalene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=CC=CC=C2C=C1I

Technology Process of 2-Iodo-3-methoxynaphthalene

There total 7 articles about 2-Iodo-3-methoxynaphthalene 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: 92.0%

2-Methoxynaphthalene (93-04-9) → 3-iodo-2-methoxynaphthalene (795278-91-0)

Guidance literature:

2-Methoxynaphthalene; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Inert atmosphere;

With iodine; In tetrahydrofuran; hexane; regioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201300552

Reference yield:

2-Methoxynaphthalene (93-04-9) → 1-iodo-2-methoxynapthalene (32721-21-4) + 3-iodo-2-methoxynaphthalene (795278-91-0)

Guidance literature:

With iodine; ferric nitrate; phosphotungstic acid; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1139/v05-187

Reference yield:

β-naphthol (135-19-3) → 3-iodo-2-methoxynaphthalene (795278-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere

2.2: 26 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201704345

upstream raw materials:

2-amino-3-methoxynaphthalene

1-(tert-butyldimethylsilyl)-4-(4',4',5',5'-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-5-ol

dimethyl sulfate

2-Methoxynaphthalene

Downstream raw materials:

1-(tert-butyldimethylsilyl)-4-(4',4',5',5'-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-5-ol