5-Oxo-5-(4-trifluoromethylphenyl)valeronitrile

Base Information

• Chemical Name: 5-Oxo-5-(4-trifluoromethylphenyl)valeronitrile
• CAS No.: 61718-86-3
• Molecular Formula: C12H10F3NO
• Molecular Weight: 241.21
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID40605997
• Nikkaji Number: J3.575.324I
• Wikidata: Q82504507
• Mol file: 61718-86-3.mol

Synonyms:5-OXO-5-(4-TRIFLUOROMETHYLPHENYL)VALERONITRILE;61718-86-3;5-oxo-5-[4-(trifluoromethyl)phenyl]pentanenitrile;MFCD02260654;SCHEMBL7343509;DTXSID40605997;AKOS016019551;4-cyano-4'-trifluoromethylbutyrophenone;DB-296268

Chemical Property of 5-Oxo-5-(4-trifluoromethylphenyl)valeronitrile

Chemical Property:

• Vapor Pressure: 2.13E-05mmHg at 25°C
• Boiling Point: 361°C at 760 mmHg
• Flash Point: 172.1°C
• PSA: 40.86000
• Density: 1.222g/cm³
• LogP: 3.58198
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 241.07144843
• Heavy Atom Count: 17
• Complexity: 307

Purity/Quality:

95% ^*data from raw suppliers

5-Oxo-5-(4-trifluoromethylphenyl)valeronitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)CCCC#N)C(F)(F)F

Technology Process of 5-Oxo-5-(4-trifluoromethylphenyl)valeronitrile

There total 6 articles about 5-Oxo-5-(4-trifluoromethylphenyl)valeronitrile 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: 79.0%

P-toluenesulfonyl cyanide (19158-51-1) + 1-(4-(trifluoromethyl)phenyl)cyclobutan-1-ol (29480-10-2) → 5-oxo-5-[4-(trifluoromethyl)phenyl]pentanenitrile (61718-86-3)

Guidance literature:

With [2,2]bipyridinyl; [bis(acetoxy)iodo]benzene; manganese(III) triacetate dihydrate; In acetonitrile; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201510973

Reference yield: 60.0%

tert-butyl (4-cyanobutanoyl)(pyridin-2-yl)carbamate + 4-trifluoromethylphenylboronic acid (128796-39-4) → 5-oxo-5-[4-(trifluoromethyl)phenyl]pentanenitrile (61718-86-3)

Guidance literature:

With palladium diacetate; potassium carbonate; tricyclohexylphosphine; In 1,4-dioxane; at 70 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ejoc.201901396

Reference yield: 43.0%

Glutaronitrile (544-13-8) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 5-oxo-5-[4-(trifluoromethyl)phenyl]pentanenitrile (61718-86-3)

Guidance literature:

With [2,2]bipyridinyl; palladium(II) acetylacetonate; toluene-4-sulfonic acid; In water; toluene; at 80 ℃; for 24h; Schlenk technique;

DOI:10.1021/acs.joc.9b02999

upstream raw materials:

potassium cyanide

4-chloro-1-(4-(trifluoromethyl)phenyl)butan-1-one

P-toluenesulfonyl cyanide

1-(4-(trifluoromethyl)phenyl)cyclobutan-1-ol

Refernces

• 1、 Chen, Jiuxi,Hu, Maolin,Li, Renhao,Liu, Jichao,Qi, Linjun,Shao, Yinlin,Yao, Xinrong,Zhao, Zhiwei,Zhen, Qianqian. "Palladium-Catalyzed Cascade Reactions of I-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines". supporting information. p. 114 - 119. Retrieved 2020/03/25.
• 2、 Ren, Rongguo,Wu, Zhen,Xu, Yan,Zhu, Chen. "C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives". supporting information. p. 2866 - 2869. Retrieved 2016/02/27.