4-(Trifluoromethyl)phenylacetonitrile

Base Information

• Chemical Name: 4-(Trifluoromethyl)phenylacetonitrile
• CAS No.: 2338-75-2
• Molecular Formula: C9H6F3N
• Molecular Weight: 185.149
• Hs Code.: 29269090
• European Community (EC) Number: 219-052-2
• DSSTox Substance ID: DTXSID20177940
• Nikkaji Number: J213.197H
• Wikidata: Q72512263
• Mol file: 2338-75-2.mol

Synonyms:4-(Trifluoromethyl)phenylacetonitrile;2338-75-2;2-(4-(trifluoromethyl)phenyl)acetonitrile;2-[4-(trifluoromethyl)phenyl]acetonitrile;4-(Trifluoromethyl)benzyl Cyanide;Benzeneacetonitrile, 4-(trifluoromethyl)-;(4-trifluoromethyl-phenyl)-acetonitrile;[4-(Trifluoromethyl)phenyl]acetonitrile;4-TRIFLUOROMETHYLPHENYLACETONITRILE;p-Trifluoromethylbenzyl cyanide;4-trifluoromethylbenzyl cyanide;p-Trifluoromethylphenylacetonitrile;EINECS 219-052-2;4-Trifluoromethyl phenyl acetonitrile;MFCD00001921;METHYLDESOXYCHOLATE;SCHEMBL246959;4-(trifluoromethyl)benzylcyanide;DTXSID20177940;p-(Trifluoromethyl)benzyl Cyanide;HMS1734O04;4-trifluoromethyl-phenylacetonitrile;4-trifluoromethylphenyl-acetonitrile;CL8795;4-(Trifluoromethyl)benzeneacetonitrile;AKOS001174240;AB00179;AC-9796;CS-W004692;FS-1143;SY013565;2-(4-trifluoromethyl-phenyl)-acetonitrile;2-(4-(trifluoromethyl)phenyl)-acetonitrile;4-(Trifluoromethyl)phenylacetonitrile, 98%;A4911;FT-0616936;T2368;EN300-49249;W-107404;Z139720904

Chemical Property of 4-(Trifluoromethyl)phenylacetonitrile

Chemical Property:

• Appearance/Colour: white crystalline mass or needles
• Vapor Pressure: 0.0278mmHg at 25°C
• Melting Point: 47-49 °C(lit.)
• Refractive Index: 1.457
• Boiling Point: 246 °C at 760 mmHg
• Flash Point: 90.3 °C
• PSA: 23.79000
• Density: 1.241 g/cm³
• LogP: 2.77148
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 185.04523368
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(Trifluoromethyl)phenylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): , Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-20/21/22/36/37/38
• Safety Statements: 26-37/39-26/36/37/39-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC#N)C(F)(F)F
• Uses: 4-(Trifluoromethyl)phenylacetonitrile was used in the preparation of:1,4-bis[2-cyano-2-(4-(trifluoromethyl)phenyl)vinyl]benzenecyano-substituted distyrylbenzene derivative, novel n-type organic semiconductor

Technology Process of 4-(Trifluoromethyl)phenylacetonitrile

There total 23 articles about 4-(Trifluoromethyl)phenylacetonitrile 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: 84.0%

4-trifluoromethylphenylboronic acid (128796-39-4) + chloroacetonitrile (107-14-2) → 4-(Trifluoromethyl)phenylacetonitrile (2338-75-2)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate; In 1,4-dioxane; water; at 100 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/ol503213z

Reference yield: 79.0%

trimethylsilyl cyanide (7677-24-9) + 4-trifluoromethylbenzoic acid (455-24-3) → 4-(Trifluoromethyl)phenylacetonitrile (2338-75-2)

Guidance literature:

4-trifluoromethylbenzoic acid; With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; iodine; In chloroform; at 60 ℃; Inert atmosphere;

trimethylsilyl cyanide; With tetrabutyl ammonium fluoride; In tetrahydrofuran; chloroform; at 60 ℃; for 5h; Reagent/catalyst; chemoselective reaction; Inert atmosphere;

DOI:10.1055/s-0033-1339903

Reference yield: 78.0%

2-trimethylsilylacetonitrile (18293-53-3) + p-trifluoromethylphenyl bromide (402-43-7) → 4-(Trifluoromethyl)phenylacetonitrile (2338-75-2)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; zinc(II) fluoride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 90 ℃; for 18h;

DOI:10.1021/ja053027x

upstream raw materials:

sodium cyanide

4-trifluoromethylbenzyl chloride

4-bromomethyltrifluoromethylbenzene

potassium cyanide

Downstream raw materials:

2-methyl-2-(4-(trifluoromethyl)phenyl)propanenitrile

4-Trifluoromethylphenylacetic acid

2-(4-trifluoromethyl-phenyl)-ethylamine

Z-2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl)acrylonitrile

Refernces

• 1、 Weweler, Jens,Younas, Sara L.,Streuff, Jan. "Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism". supporting information. p. 17700 - 17703. Retrieved 2019/11/13.
• 2、 Nambo, Masakazu,Yar, Muhammad,Smith, Joel D.,Crudden, Cathleen M.. "The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes". supporting information. p. 50 - 53. Retrieved 2015/07/28.