4-(2,2,2-Trifluoroethoxy)benzonitrile

Base Information

• Chemical Name: 4-(2,2,2-Trifluoroethoxy)benzonitrile
• CAS No.: 56935-76-3
• Molecular Formula: C9H6F3NO
• Molecular Weight: 201.148
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID30449640
• Nikkaji Number: J1.062.355C
• Wikidata: Q82269164
• Mol file: 56935-76-3.mol

Synonyms:4-(2,2,2-trifluoroethoxy)benzonitrile;56935-76-3;SCHEMBL2323409;DTXSID30449640;MFCD00511903;STL412522;AKOS000198033;BS-32575;4-(2,2,2-Trifluoro-ethoxy)-benzonitrile;CS-0119927;FT-0692289;EN300-27065;Z235344689

Chemical Property of 4-(2,2,2-Trifluoroethoxy)benzonitrile

Chemical Property:

• Vapor Pressure: 0.027mmHg at 25°C
• Refractive Index: 1.462
• Boiling Point: 246.449 °C at 760 mmHg
• Flash Point: 102.849 °C
• PSA: 33.02000
• Density: 1.29 g/cm³
• LogP: 2.49938
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 201.04014830
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

4-(2,2,2-trifluoroethoxy)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)OCC(F)(F)F

Technology Process of 4-(2,2,2-Trifluoroethoxy)benzonitrile

There total 19 articles about 4-(2,2,2-Trifluoroethoxy)benzonitrile 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: 96.0%

2,2,2-trifluoroethanol (75-89-8) + 4-bromobenzenecarbonitrile (623-00-7) → 4-(2',2',2'-trifluoroethoxy)nitrobenzonitrile (56935-76-3)

Guidance literature:

2,2,2-trifluoroethanol; 4-bromobenzenecarbonitrile; With nickel(II) chloride hexahydrate; cadmium(II) sulphide; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl acetamide; for 0.00277778h; Schlenk technique; Sonication;

In N,N-dimethyl acetamide; at 20 ℃; Schlenk technique; Irradiation;

DOI:10.1039/c9cc00987f

Reference yield: 96.0%

4-bromobenzenecarbonitrile (623-00-7) + [(1,10-phenanthroline)2Cu][OCH2CF3] → 4-(2',2',2'-trifluoroethoxy)nitrobenzonitrile (56935-76-3)

Guidance literature:

With sodium t-butanolate; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.201501257

Reference yield: 95.0%

4-Cyanochlorobenzene (623-03-0) + C8H8BF12O4(1-)*Na(1+) → 4-(2',2',2'-trifluoroethoxy)nitrobenzonitrile (56935-76-3)

Guidance literature:

4-Cyanochlorobenzene; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos; In tert-Amyl alcohol; at 20 ℃; for 0.0833333h; Inert atmosphere;

C₈H₈BF₁₂O₄^(1-)*Na⁽¹⁺⁾; In tert-Amyl alcohol; at 100 ℃; for 4h; Inert atmosphere;

DOI:10.1002/chem.201704205

upstream raw materials:

4-Cyanochlorobenzene

2,2,2-trifluoroethanol

sodium 2,2,2-trifluoroethanolate

4-fluorobenzonitrile

Downstream raw materials:

3-chloro-4-2',2',2'-trifluoroethoxybenzonitrile

4-(2',2',2'-Trifluoroethoxy)benzamide

4-(2',2',2'-Trifluoroethoxy)benzoylthiosemicarbazide

4-(2',2',2'-Trifluoroethoxy)benzoylhydrazide

Refernces

• 1、 Liu, Yi-Yin,Liang, Dong,Lu, Liang-Qiu,Xiao, Wen-Jing. "Practical heterogeneous photoredox/nickel dual catalysis for C-N and C-O coupling reactions". supporting information. p. 4853 - 4856. Retrieved 2019/05/02.
• 2、 Wang, Dong-Yu,Yang, Ze-Kun,Wang, Chao,Zhang, Ao,Uchiyama, Masanobu. "From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions". supporting information. p. 3641 - 3645. Retrieved 2018/03/13.