1,6-Dimethoxynaphthalene

Base Information

• Chemical Name: 1,6-Dimethoxynaphthalene
• CAS No.: 3900-49-0
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• Hs Code.: 2909309090
• European Community (EC) Number: 625-845-8
• NSC Number: 167477
• DSSTox Substance ID: DTXSID30304821
• Nikkaji Number: J3.020.392E
• Wikidata: Q72468100
• Mol file: 3900-49-0.mol

Synonyms:1,6-Dimethoxynaphthalene;3900-49-0;2,5-Dimethoxynaphthalene;Naphthalene, 1,6-dimethoxy-;MFCD00086330;1,6-Dimethoxy naphthalene;NSC167477;1,6-dimethoxynaphtalene;1,6-dimethoxynapthalene;Maybridge3_002840;1,6-Dimethoxyl naphthalene;SCHEMBL443271;1,6-Dimethoxynaphthalene, 97%;DTXSID30304821;RBUFUWIWCCOVOS-UHFFFAOYSA-N;HMS1439B02;CS-M0856;AKOS015909429;AB10147;NSC-167477;SS-3261;IDI1_014227;AC-24468;SY101206;FT-0607006;A18721;EN300-1179724;AE-848/02105007;Q-102772

Chemical Property of 1,6-Dimethoxynaphthalene

Chemical Property:

• Appearance/Colour: yellowish powder
• Melting Point: 56-60 °C(lit.)
• Boiling Point: 311.2 °C at 760 mmHg
• Flash Point: 130.3 °C
• PSA: 18.46000
• Density: 1.097 g/cm³
• LogP: 2.85700
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Dichloromethane
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 188.083729621
• Heavy Atom Count: 14
• Complexity: 181

Purity/Quality:

98% ^*data from raw suppliers

1,6-Dimethoxynaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-36/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C(=CC=C2)OC
• Uses: Intermediate in the production of tetralin derivatives

Technology Process of 1,6-Dimethoxynaphthalene

There total 6 articles about 1,6-Dimethoxynaphthalene 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%

1,6-dihydroxynaphthalene (575-44-0) + dimethyl sulfate (77-78-1) → 1,6-dimethoxynaphthalene (3900-49-0)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 45 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/op800285t

Reference yield: 90.0%

1,6-dihydroxynaphthalene (575-44-0) + methyl iodide (74-88-4) → 1,6-dimethoxynaphthalene (3900-49-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield: 88.0%

methanol (67-56-1) + 1-ethynyl-4-methoxy-2-(2-methoxyvinyl)benzene → 1,6-dimethoxynaphthalene (3900-49-0)

Guidance literature:

With [Au(2,6-bis(diisopropylphenyl)imidazol-2-ylidene)]SbF₆; at 80 ℃; Inert atmosphere;

DOI:10.1039/c4cc00464g

upstream raw materials:

1,6-dihydroxynaphthalene

dimethyl sulfate

methanol

1,4-dihydro-2,5-dimethoxynaphthalene

Downstream raw materials:

5-methoxy-2-tetralone

4,7-dimethoxy-1-naphthaldehyde

(Z)-2-(4,7-Dimethoxy-naphthalen-1-yl)-1,4-diphenyl-but-2-ene-1,4-dione

C₆H₅C(OH)(C₆H₃)(C₁₀H₅)(OCH₃)4

Refernces

• 1、 Donthamsetti, Prashant C.,Winter, Nils,Sch?nberger, Matthias,Levitz, Joshua,Stanley, Cherise,Javitch, Jonathan A.,Isacoff, Ehud Y.,Trauner, Dirk. "Optical Control of Dopamine Receptors Using a Photoswitchable Tethered Inverse Agonist". . p. 18522 - 18535. Retrieved 2018/01/08.
• 2、 Liu, Yongxiang,Guo, Jia,Liu, Yang,Wang, Xiaoyu,Wang, Yanshi,Jia, Xinyu,Wei, Gaofei,Chen, Lizhu,Xiao, Jianyong,Cheng, Maosheng. "Au(i)-catalyzed triple bond alkoxylation/dienolether aromaticity-driven cascade cyclization to naphthalenes". supporting information. p. 6243 - 6245. Retrieved 2014/06/09.