Methyl 3-(trifluoroMethylsulfonyloxy)-2-naphthoate

Base Information

• Chemical Name: Methyl 3-(trifluoroMethylsulfonyloxy)-2-naphthoate
• CAS No.: 288402-18-6
• Molecular Formula: C13H9F3O5S
• Molecular Weight: 334.273
• Mol file: 288402-18-6.mol

Synonyms:methyl 3-(trifluoromethylsulfonyloxy)-2-naphthoate;methyl 2-naphthoate-3-trifluoromethanesulfonate;3-{[(trifluoromethyl)sulfonyl]oxy}-naphthalene-2-carboxylic acid methyl ester;

Chemical Property of Methyl 3-(trifluoroMethylsulfonyloxy)-2-naphthoate

Chemical Property:

• Boiling Point: 421.9±45.0 °C(Predicted)
• PSA: 78.05000
• Density: 1.499±0.06 g/cm3(Predicted)
• LogP: 3.93560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 3-(trifluoroMethylsulfonyloxy)-2-naphthoate

There total 3 articles about Methyl 3-(trifluoroMethylsulfonyloxy)-2-naphthoate 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: 98.0%

3-hydroxy-2-naphthoic acid methyl ester (883-99-8) + trifluoromethylsulfonic anhydride (358-23-6) → methyl 3-(trifluoromethanesulfonyloxy)naphthalene-2-carboxylate (288402-18-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1002/anie.201707099

Reference yield: 95.0%

3-hydroxy-2-naphthoic acid methyl ester (883-99-8) + trifluorormethanesulfonic acid (1493-13-6) → methyl 3-(trifluoromethanesulfonyloxy)naphthalene-2-carboxylate (288402-18-6)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere; Cooling with ice;

Reference yield:

3-Hydroxy-2-naphthoic acid (92-70-6) → methyl 3-(trifluoromethanesulfonyloxy)naphthalene-2-carboxylate (288402-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C

2: triethylamine / dichloromethane / -78 - 20 °C / Inert atmosphere

With caesium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol400877q

upstream raw materials:

3-hydroxy-2-naphthoic acid methyl ester

trifluoromethylsulfonic anhydride

3-Hydroxy-2-naphthoic acid

trifluorormethanesulfonic acid

Downstream raw materials:

3-phenyl-2-naphthioc acid

methyl 3-phenylnaphthalene-2-carboxylate

2-hydroxymethyl-3-methylnaphthalene

Refernces

• 1、 Tamura, Risa,Kitamura, Eriko,Tsutsumi, Ryosuke,Yamanaka, Masahiro,Akiyama, Takahiko,Mori, Keiji. "Diastereoselective Synthesis of CF3-Substituted Spiroisochromans by [1,5]-Hydride Shift/Cyclization/Intramolecular Friedel-Crafts Reaction Sequence". . p. 2383 - 2387. Retrieved 2019.
• 2、 -. "COMPOUND, COMPOSITION, ORGANIC ELECTROLUMINESCENT ELEMENT, AND ELECTRONIC APPLIANCE". Paragraph 0582-0583. . Retrieved 2019/11/21.