methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate

Base Information

• Chemical Name: methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate
• CAS No.: 887360-34-1
• Molecular Formula: C₁₁H₈F₃NO₂
• Molecular Weight: 243.185
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID80427998
• Nikkaji Number: J2.475.482K
• Wikidata: Q82240762
• Mol file: 887360-34-1.mol

Synonyms:methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate;887360-34-1;methyl 6-(trifluoromethyl)indole-2-carboxylate;6-trifluoromethyl-1H-indole-2-carboxylic acid methyl ester;SCHEMBL926647;DTXSID80427998;MFCD07357592;AKOS005144350;TS-03380;CS-0094445;FT-0747646;EN300-247243;A847199;methyl6-(trifluoromethyl)-1H-indole-2-carboxylate;J-522519;6-(Trifluoromethyl)-1H-indole-2-carboxylic acid methyl ester

Chemical Property of methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate

Chemical Property:

• Melting Point: 169.8-170.8℃
• PSA: 42.09000
• LogP: 2.97330
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 243.05071298
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

98%min ^*data from raw suppliers

Methyl6-(Trifluoromethyl)-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Statements: 36-37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(N1)C=C(C=C2)C(F)(F)F

Technology Process of methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate

There total 4 articles about methyl 6-(trifluoromethyl)-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: 93.0%

methanol (67-56-1) + 6-(trifluoromethyl)-1H-indole-2-carboxylic acid (327-20-8) → methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate (887360-34-1)

Guidance literature:

6-(trifluoromethyl)-1H-indole-2-carboxylic acid; With oxalyl dichloride; In dichloromethane; at 20 ℃; for 0.666667h; Inert atmosphere;

methanol; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.bmcl.2017.02.005

Reference yield: 88.0%

(Z)-methyl 2-azido-3-(4-(trifluoromethyl)phenyl)acrylate → methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate (887360-34-1)

Guidance literature:

Rh₂(pbf)4; In toluene; at 60 ℃; for 16h;

DOI:10.1021/ja072219k

Reference yield:

4-Trifluoromethylbenzaldehyde (455-19-6) → methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate (887360-34-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / sodium methoxide / methanol / 4 h / -10 °C

2: 88 percent / Rh₂(pbf)4 / toluene / 16 h / 60 °C

With sodium methylate; Rh₂(pbf)4; In methanol; toluene;

DOI:10.1021/ja072219k

upstream raw materials:

4-Trifluoromethylbenzaldehyde

methanol

6-(trifluoromethyl)-1H-indole-2-carboxylic acid

Refernces

• 1、 Bonnamour, Julien,Bolm, Carsten. "Iron(II) triflate as a catalyst for the synthesis of indoles by intramolecular C-H amination". supporting information; experimental part. p. 2012 - 2014. Retrieved 2011/06/28.