2-(4-Fluorophenyl)propanenitrile

Base Information

• Chemical Name: 2-(4-Fluorophenyl)propanenitrile
• CAS No.: 51965-61-8
• Molecular Formula: C9H8 F N
• Molecular Weight: 149.168
• Hs Code.: 2926909090
• European Community (EC) Number: 257-563-2
• DSSTox Substance ID: DTXSID00966293
• Nikkaji Number: J127.106G
• Mol file: 51965-61-8.mol

Synonyms:2-(4-Fluorophenyl)propanenitrile;51965-61-8;2-(4-Fluorophenyl)propiononitrile;EINECS 257-563-2;C9H8FN;Benzeneacetonitrile, 4-fluoro-.alpha.-methyl-;SCHEMBL8088810;C9-H8-F-N;2-(4-fluorophenyl)propanonitrile;DTXSID00966293;2-(4-Fluorophenyl)propanenitrile #;p-Fluoro-alpha-methylphenylacetonitrile;AT19993;4-fluoro-alpha-methylbenzeneacetonitrile;CS-0238234;EN300-191809

Chemical Property of 2-(4-Fluorophenyl)propanenitrile

Chemical Property:

• Vapor Pressure: 0.111mmHg at 25°C
• Boiling Point: 220.7°C at 760 mmHg
• Flash Point: 86.4°C
• PSA: 23.79000
• Density: 1.087g/cm³
• LogP: 2.45278
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 149.064077422
• Heavy Atom Count: 11
• Complexity: 162

Purity/Quality:

98%Min ^*data from raw suppliers

2-(4-Fluorophenyl)propanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 2-(4-Fluorophenyl)propanenitrile

There total 22 articles about 2-(4-Fluorophenyl)propanenitrile 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: 100.0%

para-fluorostyrene (405-99-2) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 4-fluoro-α-methylbenzeneacetonitrile (51965-61-8)

Guidance literature:

With 3-[bis-(4-methoxy-phenyl)-phosphanyl]-2H-isoquinolin-1-one; N-{6-[bis-(4-methoxy-phenyl)-phosphanyl]-pyridin-2-yl}-2,2-dimethyl-propionamide; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In toluene; at 35 ℃; for 25h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.200805092

Reference yield: 95.0%

potassium cyanide + para-fluorostyrene (405-99-2) → 4-fluoro-α-methylbenzeneacetonitrile (51965-61-8)

Guidance literature:

potassium cyanide; With acetic acid; In ethylene glycol; at 60 ℃; Sealed tube;

para-fluorostyrene; With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; at 60 ℃; for 18h; Sealed tube;

DOI:10.1039/c7sc03912c

Reference yield: 88.0%

2-(4-fluorophenyl)propanal oxime → 4-fluoro-α-methylbenzeneacetonitrile (51965-61-8)

Guidance literature:

With copper diacetate; In acetonitrile; Reflux;

DOI:10.1002/anie.202017234

upstream raw materials:

acetoxy(4-fluorophenyl)acetonitrile

4-fluorophenylacetonitrile

carbonic acid dimethyl ester

methyl iodide

Downstream raw materials:

(S)-4-fluoro-α-methylphenylacetic acid

2-(4-Fluorphenyl)-3-morpholinoacrylonitril

Refernces

• 1、 Shee, Sujan,Kundu, Sabuj. "Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol". . p. 6943 - 6951. Retrieved 2021/05/29.
• 2、 Frye, Nils L.,Bhunia, Anup,Studer, Armido. "Nickel-Catalyzed Markovnikov Transfer Hydrocyanation in the Absence of Lewis Acid". supporting information. p. 4456 - 4460. Retrieved 2020/06/03.