2-(4-Fluorophenyl)-2-phenylacetonitrile

Base Information

• Chemical Name: 2-(4-Fluorophenyl)-2-phenylacetonitrile
• CAS No.: 719-82-4
• Molecular Formula: C14H10 F N
• Molecular Weight: 211.239
• NSC Number: 23818
• DSSTox Substance ID: DTXSID90282010
• Nikkaji Number: J3.113.668G
• Mol file: 719-82-4.mol

Synonyms:2-(4-fluorophenyl)-2-phenylacetonitrile;719-82-4;2-(4-Fluorophenyl)-2-phenyl acetonitrile;2-(4-fluorophenyl)-2-phenyl-acetonitrile;NSC23818;SCHEMBL5052368;DTXSID90282010;LRNPWSOSXVCRKG-UHFFFAOYSA-N;AR3584;MFCD00019794;NSC-23818;AKOS025404263;CS-0200007;A914431

Chemical Property of 2-(4-Fluorophenyl)-2-phenylacetonitrile

Chemical Property:

• Vapor Pressure: 0.000511mmHg at 25°C
• Melting Point: 39-41 °C
• Boiling Point: 313°C at 760 mmHg
• Flash Point: 134.2°C
• PSA: 23.79000
• Density: 1.149g/cm³
• LogP: 3.48118
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 211.079727485
• Heavy Atom Count: 16
• Complexity: 253

Purity/Quality:

99% ^*data from raw suppliers

2-(4-Fluorophenyl)-2-phenylacetonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C#N)C2=CC=C(C=C2)F
• Uses: 2-(4-Fluorophenyl)-2-phenylacetonitrile is used as a reagent in the synthesis of unsymmetric triarylacetonitriles via palladium-catalyzed sequential arylations from chloroacetonitrile and further conversion to tri- and tetraarylmethanes.

Technology Process of 2-(4-Fluorophenyl)-2-phenylacetonitrile

There total 13 articles about 2-(4-Fluorophenyl)-2-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-fluorophenyl tosylate (1582-01-0) + phenylacetonitrile (140-29-4) → 2-(4-fluorophenyl)-2-phenylacetonitrile (719-82-4)

Guidance literature:

With potassium phosphate; palladium diacetate; XPhos; In dichloromethane; tert-butyl alcohol; at 110 ℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1002/ejoc.202000176

Reference yield: 80.0%

trimethylsilyl cyanide (7677-24-9) + 4-fluorobenzhydrol (149099-27-4,149243-88-9,365-22-0) → 2-(4-fluorophenyl)-2-phenylacetonitrile (719-82-4)

Guidance literature:

With zinc trifluoromethanesulfonate; In nitromethane; at 100 ℃; for 6h;

DOI:10.1016/j.tetlet.2012.08.021

Reference yield: 74.0%

phenylacetonitrile (140-29-4) + 1-Bromo-4-fluorobenzene (460-00-4) → 2-(4-fluorophenyl)-2-phenylacetonitrile (719-82-4)

Guidance literature:

With potassium phosphate; dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate; In 1,4-dioxane; at 80 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/ol503213z

upstream raw materials:

fluorobenzene

bromo-phenyl-acetonitrile

benzene

4-fluorophenylacetonitrile

Downstream raw materials:

2-(4-fluoro-phenyl)-2-phenyl-ethylamine

4-fluorobenzophenone

2-(2-{2-[(4-fluoro-phenyl)-phenyl-methyl]-thiazol-4-yl}-ethyl)-isoindole-1,3-dione

2-(4-fluoro-phenyl)-2-phenyl-thioacetamide

Refernces

• 1、 Yuen, On Ying,Chen, Xiangmeng,Wu, Junyu,So, Chau Ming. "Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates". supporting information. p. 1912 - 1916. Retrieved 2020/03/13.
• 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.