2-Hydroxy-2-[4-(trifluoromethyl)phenyl]acetonitrile

Base Information

• Chemical Name: 2-Hydroxy-2-[4-(trifluoromethyl)phenyl]acetonitrile
• CAS No.: 168013-75-0
• Molecular Formula: C9H6F3NO
• Molecular Weight: 201.148
• DSSTox Substance ID: DTXSID70558568
• Nikkaji Number: J2.898.176G
• Mol file: 168013-75-0.mol

Synonyms:2-hydroxy-2-[4-(trifluoromethyl)phenyl]acetonitrile;168013-75-0;Benzeneacetonitrile, .alpha.-hydroxy-4-(trifluoromethyl)-;alpha-Hydroxy-4-(trifluoromethyl)benzeneacetonitrile;SCHEMBL6908520;Benzeneacetonitrile,.alpha.-hydroxy-4-(trifluoromethyl)-;DTXSID70558568;NYWXAQVYSYFVIG-UHFFFAOYSA-N;MFCD12169340;AKOS009469237;BS-16192;CS-0161351;Hydroxy[4-(trifluoromethyl)phenyl]acetonitrile;D80859;EN300-174665;J-519676

Chemical Property of 2-Hydroxy-2-[4-(trifluoromethyl)phenyl]acetonitrile

Chemical Property:

• PSA: 44.02000
• LogP: 2.26238
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 201.04014830
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

98%Min ^*data from raw suppliers

2-hydroxy-2-[4-(trifluoromethyl)phenyl]acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Hydroxy-2-[4-(trifluoromethyl)phenyl]acetonitrile

There total 10 articles about 2-Hydroxy-2-[4-(trifluoromethyl)phenyl]acetonitrile 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: 95.0%

4-Trifluoromethylbenzaldehyde (455-19-6) + trimethylsilyl cyanide (7677-24-9) → (+/-)-2-hydroxy-2-(4-trifluoromethylphenyl)acetonitrile (168013-75-0)

Guidance literature:

With bis(triphenylphosphine)iododioxorhenium(V); In tetrahydrofuran; at 60 ℃;

DOI:10.1021/ja0433424

Reference yield: 90.0%

4-Trifluoromethylbenzaldehyde (455-19-6) + 2-hydroxy-2,2-diphenylacetonitrile (4746-48-9) → benzophenone (119-61-9) + (+/-)-2-hydroxy-2-(4-trifluoromethylphenyl)acetonitrile (168013-75-0)

Guidance literature:

With dibutyldimethoxytin; In diethyl ether; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/adsc.201000409

Reference yield: 67.0%

4-Trifluoromethylbenzaldehyde (455-19-6) + hydrogen cyanide (74-90-8) → (+/-)-2-hydroxy-2-(4-trifluoromethylphenyl)acetonitrile (168013-75-0)

Guidance literature:

With almond meal; In di-isopropyl ether; at 12 ℃; for 24h;

DOI:10.1016/S0957-4166(01)00145-8

upstream raw materials:

2-(4-(trifluoromethyl)phenyl)-2-((trimethylsilyl)oxy)acetonitrile

4-Trifluoromethylbenzaldehyde

hydrogen cyanide

trimethylsilyl cyanide

Downstream raw materials:

(S)-2-hydroxy(4-trifluoromethylphenyl)acetonitrile

(R)-2-(4-fluorophenyl)-2-hydroxyacetonitrile

α-acetoxy-4-(trifluoromethyl)benzeneacetonitrile

4-Trifluoromethylbenzaldehyde

Refernces

• 1、 Kim, Kicheol,Moeljadi, Adhitya Mangala Putra,Hirao, Hajime,Hong, Soon Hyeok. "Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex". supporting information. p. 3292 - 3298. Retrieved 2017/09/06.
• 2、 Zhang, Zhiguo,Lippert, Katharina M.,Hausmann, Heike,Kotke, Mike,Schreiner, Peter R.. "Cooperative thiourea-Bronsted acid organocatalysis: Enantioselective cyanosilylation of aldehydes with TMSCN". experimental part. p. 9764 - 9776. Retrieved 2012/01/03.