2-Bromo-6-methoxynaphthalene

Base Information

• Chemical Name: 2-Bromo-6-methoxynaphthalene
• CAS No.: 5111-65-9
• Molecular Formula: C11H9BrO
• Molecular Weight: 237.096
• Hs Code.: 29093090
• European Community (EC) Number: 225-837-0
• NSC Number: 3236
• UNII: S19T080MRG
• DSSTox Substance ID: DTXSID10199116
• Nikkaji Number: J203.303H
• Wikidata: Q27288440
• Mol file: 5111-65-9.mol

Synonyms:2-Bromo-6-methoxynaphthaline;2-Methoxy-6-bromonaphthalene;6-Bromo-2-methoxynaphthalene;6-Methoxy-2-bromonaphthalene;NSC 3236;

Chemical Property of 2-Bromo-6-methoxynaphthalene

Chemical Property:

• Appearance/Colour: white to light beige powder
• Vapor Pressure: 0.000459mmHg at 25°C
• Melting Point: 106-109 °C(lit.)
• Refractive Index: 1.632
• Boiling Point: 324.7 °C at 760 mmHg
• Flash Point: 134.7 °C
• PSA: 9.23000
• Density: 1.447 g/cm³
• LogP: 3.61090
• Storage Temp.: Room temperature.
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• Water Solubility.: Soluble in DMSO. Insoluble in water.
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 235.98368
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-6-methoxynaphthalene(NaproxenImpurityN) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C=C(C=C2)Br
• Uses: Naproxen Impurity N. 2-Bromo-6-methoxynaphthalene is used in the synthesis of nabumetone [4-(6-methoxy-2-naphthalenyl)-2-butanone] by Heck reaction.

Technology Process of 2-Bromo-6-methoxynaphthalene

There total 30 articles about 2-Bromo-6-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: 99.0%

6-bromo-naphthalen-2-ol (15231-91-1) + methyl bromide (74-83-9) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Guidance literature:

With potassium carbonate; In acetonitrile; for 3h; Reflux;

DOI:10.1039/c2jm32448b

Reference yield: 98.0%

2-Methoxynaphthalene (93-04-9) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Guidance literature:

With hydrogen bromide; sodium bromide; In chloroform; water; at 0 ℃; Electrochemical reaction;

DOI:10.1016/j.tetlet.2006.04.152

Reference yield: 97.0%

6-bromo-naphthalen-2-ol (15231-91-1) + methyl iodide (74-88-4) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1021/cg401522v

upstream raw materials:

methanol

6-bromo-naphthalen-2-ol

6-bromo-2-methoxy-1-naphthoic acid

dimethyl sulfate

Downstream raw materials:

2-(6-methoxy-2-naphthoyl)benzoic acid

nabumetone

4-(6-methoxy-2-naphthyl)-3-butene-2-ol

4-(6'-methoxy-2'-naphthyl)-3-buten-2-one

Refernces

• 1、 Ter Wiel, Matthijs K. J.,Feringa, Ben L.. "Synthesis of functionalized molecular motors". . p. 1789 - 1796. Retrieved 2005.
• 2、 Cai, Zongyu,Deng, Liming,Geng, Xinqian,Hu, Lijun,Jiao, Shixuan,Li, Zheng,Ren, Qiang,Wang, Bin,Yang, Ying,Zhang, Luyong,Zhou, Zongtao. "Discovery of new and highly effective quadruple FFA1 and PPARα/γ/δ agonists as potential anti-fatty liver agents". supporting information. . Retrieved 2021/12/27.
• 3、 Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo. "Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons". supporting information. p. 1297 - 1300. Retrieved 2020/12/23.