ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate

Base Information

• Chemical Name: ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate
• CAS No.: 175203-82-4
• Molecular Formula: C₁₂H₁₀F₃NO₃
• Molecular Weight: 273.212
• Hs Code.: 2933990090
• European Community (EC) Number: 670-581-9
• DSSTox Substance ID: DTXSID10371930
• Wikidata: Q82159477
• Mol file: 175203-82-4.mol

Synonyms:175203-82-4;ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate;Ethyl 5-(trifluoromethoxy)indole-2-carboxylate;Maybridge1_005094;SCHEMBL384385;HMS555P12;DTXSID10371930;AMY17642;MFCD00219837;AKOS007930755;CCG-246345;TS-00919;CS-0315101;FT-0626112;ethyl5-(trifluoromethoxy)indole-2-carboxylate;A811888;ethyl 5-trifluoromethyloxy-1H-indole-2-carboxylate;ethyl5-(trifluoromethoxy)-1H-indole-2-carboxylate;3-ethyl-5-(trifluoromethoxy)-1H-indole-2-carboxylate;5-trifluoromethoxy-1H-indole-2-carboxylic acid ethyl ester;1H-Indole-2-carboxylicacid,5-(trifluoromethoxy)-,ethyl ester

Chemical Property of ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 1.1E-06mmHg at 25°C
• Melting Point: 144 °C
• Boiling Point: 339.9°Cat760mmHg
• Flash Point: 159.4°C
• PSA: 51.32000
• Density: 1.389g/cm³
• LogP: 3.24320
• Storage Temp.: 2-8°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 273.06127767
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 5-(trifluoromethoxy)indole-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(N1)C=CC(=C2)OC(F)(F)F

Technology Process of ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate

There total 3 articles about ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate 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: 60.0%

2-oxo-propionic acid ethyl ester (617-35-6) + 4-(trifluoromethoxy)aniline (461-82-5) → ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate (175203-82-4)

Guidance literature:

With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 80 ℃; for 24h; under 760.051 Torr; Schlenk technique; Molecular sieve;

DOI:10.1021/acs.joc.8b02180

Reference yield:

Ethyl isocyanoacetate (2999-46-4) + 2-bromo-5-(trifluoromethoxy)benzaldehyde (505084-61-7) → ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate (175203-82-4)

Guidance literature:

With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 50 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b00928

Reference yield:

ethanol (64-17-5) + 5-(trifluoromethoxy)-1H-indole-2-carboxylic acid (175203-84-6) → ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylate (175203-82-4)

Guidance literature:

With sulfuric acid; Reflux;

DOI:10.1021/acs.jmedchem.9b01626

upstream raw materials:

Ethyl isocyanoacetate

2-bromo-5-(trifluoromethoxy)benzaldehyde

2-oxo-propionic acid ethyl ester

4-(trifluoromethoxy)aniline

Refernces

• 1、 -. "Synthesis method for preparing 2-substituted indole derivative". Paragraph 0131-0134. . Retrieved 2019/05/28.
• 2、 Temple, Kayla J.,Duvernay, Matthew T.,Young, Summer E.,Wen, Wandong,Wu, Wenjun,Maeng, Jae G.,Blobaum, Anna L.,Stauffer, Shaun R.,Hamm, Heidi E.,Lindsley, Craig W.. "Development of a series of (1-benzyl-3-(6-methoxypyrimidin-3-yl)-5-(trifluoromethoxy)-1h-indol-2-yl)methanols as selective protease activated receptor 4 (PAR4) antagonists with in vivo utility and activity against γ-thrombin". supporting information. p. 7690 - 7695. Retrieved 2016/09/04.