2,6-Bis(trifluoromethyl)phenol

Base Information

• Chemical Name: 2,6-Bis(trifluoromethyl)phenol
• CAS No.: 46377-35-9
• Molecular Formula: C8H4F6O
• Molecular Weight: 230.10700
• DSSTox Substance ID: DTXSID60438946
• Nikkaji Number: J1.040.446K
• Wikidata: Q82254796
• Mol file: 46377-35-9.mol

Synonyms:2,6-bis(trifluoromethyl)phenol;46377-35-9;SCHEMBL396017;2,6-bis(trifluoromethyl)-phenol;DTXSID60438946;WMTYURHKRZDHAM-UHFFFAOYSA-N;AMY41120;AKOS016344398;AB93070;BB 0261468;CS-0311951;FT-0712401;F13343

Chemical Property of 2,6-Bis(trifluoromethyl)phenol

Chemical Property:

• Boiling Point: 142.6±35.0 °C(Predicted)
• PKA: 6.00±0.50(Predicted)
• PSA: 20.23000
• Density: 1.485±0.06 g/cm3(Predicted)
• LogP: 3.42980
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 230.01663372
• Heavy Atom Count: 15
• Complexity: 198

Purity/Quality:

99%, ^*data from raw suppliers

2,6-Bis(trifluoromethyl)phenol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)C(F)(F)F)O)C(F)(F)F
• Uses: 2,6-Bis(trifluoromethyl)phenol is a useful intermediate for the preparation of tebufelone analogs.

Technology Process of 2,6-Bis(trifluoromethyl)phenol

There total 4 articles about 2,6-Bis(trifluoromethyl)phenol 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: 47.0%

trifluoromethylcopper(I) (77152-08-0) + 2-iodo-6-(trifluoromethyl)phenol (149209-48-3) → 2,6-bis(trifluoromethyl)phenol (46377-35-9)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; at 60 ℃; for 1.5h;

DOI:10.1021/jo00061a048

Reference yield:

2-(trifluoromethyl)phenol (444-30-4) → 2,6-bis(trifluoromethyl)phenol (46377-35-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / p-TsOH*H₂O / diethyl ether / 18 h / Heating

2: 1) BuLi, 2) iodine / 1) THF, -78 deg C, 30 min, 2) a) THF, -78 deg C, 10 min, b) to room temperature

3: 47 percent / dimethylformamide; hexamethylphosphoric acid triamide / 1.5 h / 60 °C

With n-butyllithium; iodine; toluene-4-sulfonic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo00061a048

Reference yield:

2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane (149209-47-2) → 2,6-bis(trifluoromethyl)phenol (46377-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) BuLi, 2) iodine / 1) THF, -78 deg C, 30 min, 2) a) THF, -78 deg C, 10 min, b) to room temperature

2: 47 percent / dimethylformamide; hexamethylphosphoric acid triamide / 1.5 h / 60 °C

With n-butyllithium; iodine; In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;

DOI:10.1021/jo00061a048

upstream raw materials:

trifluoromethylcopper(I)

2-iodo-6-(trifluoromethyl)phenol

phenyllithium

2-(trifluoromethyl)phenol

Downstream raw materials:

2,6-bis(trifluoromethyl)-4-bromophenol TBDMS ether

1-[4-(tert-Butyl-dimethyl-silanyloxy)-3,5-bis-trifluoromethyl-phenyl]-hex-5-yn-1-one

2,6-bis(trifluoromethyl)-4-bromophenol

Refernces

• 1、 Boche, Gernot,Bosold, Ferdinand,Lohrenz, John C. W.,Opel, Achim,Zulauf, Peter. "α-Oxygen-Substituted Organolithium Compounds and their Carbenoid Nature: Reactions with RLi and Other Nucleophiles, Experimental and IGLO-Calculated 13C-NMR Shifts of the Carbenoid C Atom". . p. 1873 - 1886. Retrieved 2007/10/02.