3-(2,2,2-Trifluoroacetyl)benzonitrile

Base Information

• Chemical Name: 3-(2,2,2-Trifluoroacetyl)benzonitrile
• CAS No.: 23568-85-6
• Molecular Formula: C9H4F3NO
• Molecular Weight: 199.13
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID70570003
• Wikidata: Q82457289
• Mol file: 23568-85-6.mol

Synonyms:3-(2,2,2-Trifluoroacetyl)benzonitrile;23568-85-6;3'-CYANO-2,2,2-TRIFLUOROACETOPHENONE;3-(trifluoroacetyl)benzonitrile;MFCD01319970;SCHEMBL1467062;DTXSID70570003;MWGVWNKZGXDSRJ-UHFFFAOYSA-N;AKOS006276760;Benzonitrile, 3-(2,2,2-trifluoroacetyl)-;EN300-1933411

Chemical Property of 3-(2,2,2-Trifluoroacetyl)benzonitrile

Chemical Property:

• Vapor Pressure: 0.0277mmHg at 25°C
• Boiling Point: 246.1°C at 760 mmHg
• Flash Point: 102.6°C
• PSA: 40.86000
• Density: 1.36g/cm³
• LogP: 2.30328
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 199.02449824
• Heavy Atom Count: 14
• Complexity: 276

Purity/Quality:

color value 30 (E1%,1cm,5) ^*data from raw suppliers

3'-Cyano-2,2,2-trifluoroacetophenone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)C(=O)C(F)(F)F)C#N
• Uses: 3-(Trifluoroacetyl)Benzonitrile is a useful reagent in the preparation of 3,?5-disubstituted and 1,?3,?5-trisubstituted benzamides with potential reversible inhibitory functions against HRV protease 3C.

Technology Process of 3-(2,2,2-Trifluoroacetyl)benzonitrile

There total 3 articles about 3-(2,2,2-Trifluoroacetyl)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: 44.0%

TurboGrignard (807329-97-1) + 2,2,2-trifluoroethyl trifluoroacetate (407-38-5) + 3-iodobenzonitrile (69113-59-3) → 3-cyano-2,2,2-trifluoroacetophenone (23568-85-6) + 3-(2,2,2-trifluoro-1-hydroxyethyl)benzonitrile + C12H12F3NO

Guidance literature:

TurboGrignard; 3-iodobenzonitrile; With toluene; In tetrahydrofuran; at -40 - -25 ℃; for 0.583333h; Inert atmosphere;

2,2,2-trifluoroethyl trifluoroacetate; In tetrahydrofuran; toluene; at -40 ℃; Inert atmosphere;

DOI:10.1002/ejoc.202000550

Reference yield:

methyl 3-cyanobenzoate (13531-48-1) + (trifluoromethyl)trimethylsilane (81290-20-2) → 3-cyano-2,2,2-trifluoroacetophenone (23568-85-6)

Guidance literature:

With cesium fluoride; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.bmc.2007.12.030

Reference yield:

→ 3-cyano-2,2,2-trifluoroacetophenone (23568-85-6)

Guidance literature:

aus m-Amino-trifluoracetophenon;

DOI:10.1021/jo00830a114

upstream raw materials:

methyl 3-cyanobenzoate

(trifluoromethyl)trimethylsilane

TurboGrignard

2,2,2-trifluoroethyl trifluoroacetate

Downstream raw materials:

3-(trifluoroacetyl)benzamide

3-(2,2,2-Trifluoro-1-trifluoromethyl-ethyl)-benzonitrile

Refernces

• 1、 Maugeri, Caterina,Alisi, Maria A.,Apicella, Claudia,Cellai, Luciano,Dragone, Patrizia,Fioravanzo, Elena,Florio, Saverio,Furlotti, Guido,Mangano, Giorgina,Ombrato, Rosella,Luisi, Renzo,Pompei, Raffaello,Rincicotti, Vito,Russo, Vincenzo,Vitiello, Marco,Cazzolla, Nicola. "New anti-viral drugs for the treatment of the common cold". . p. 3091 - 3107. Retrieved 2008/09/20.