2-Phenethylbenzonitrile

Base Information

• Chemical Name: 2-Phenethylbenzonitrile
• CAS No.: 5505-00-0
• Molecular Formula: C15H13N
• Molecular Weight: 207.275
• Hs Code.: 2926909090
• NSC Number: 100687
• DSSTox Substance ID: DTXSID10295228
• Nikkaji Number: J370.648F
• Wikidata: Q82035032
• ChEMBL ID: CHEMBL4067237
• Mol file: 5505-00-0.mol

Synonyms:2-phenethylbenzonitrile;2-(2-phenylethyl)benzonitrile;5505-00-0;NSC100687;SCHEMBL2507390;CHEMBL4067237;DTXSID10295228;NSC-100687

Chemical Property of 2-Phenethylbenzonitrile

Chemical Property:

• Vapor Pressure: 0.000364mmHg at 25°C
• Refractive Index: 1.591
• Boiling Point: 318.3 °C at 760 mmHg
• Flash Point: 146.9 °C
• PSA: 23.79000
• Density: 1.07 g/cm³
• LogP: 3.34348
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 207.104799419
• Heavy Atom Count: 16
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

2-(2-PHENETHYL)BENZONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC2=CC=CC=C2C#N

Technology Process of 2-Phenethylbenzonitrile

There total 16 articles about 2-Phenethylbenzonitrile 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%

2-((1E)-2-phenylvinyl)benzenecarbonitrile (80663-50-9,38175-96-1) → 2-(2-Phenethyl)benzonitrile (5505-00-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; dichloromethane; for 4h; under 760.051 Torr; Reflux;

DOI:10.1002/adsc.201600128

Reference yield: 90.0%

2-Methylbenzonitrile (529-19-1) + benzyl bromide (100-39-0) → 2-(2-Phenethyl)benzonitrile (5505-00-0)

Guidance literature:

2-Methylbenzonitrile; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

benzyl bromide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1080/00304949909355729

Reference yield: 87.0%

bromobenzene (108-86-1,52753-63-6) + 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)benzonitrile → 2-(2-Phenethyl)benzonitrile (5505-00-0)

Guidance literature:

With palladium diacetate; potassium hydroxide; ruphos; In tetrahydrofuran; water; at 80 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.0c03138

upstream raw materials:

styrene

2-Chlorobenzonitrile

2-((1E)-2-phenylvinyl)benzenecarbonitrile

lead(II) thiocyanate

Downstream raw materials:

1,1'-(1,2-ethanediyl)bisbenzene

4-Dimethylamino-1-(2-phenethyl-phenyl)-butan-1-ol

4-Dimethylamino-2'-phenethylbutyrophenon

(2-phenethylphenyl)(phenyl)methanone

Refernces

• 1、 Ansel, Annabel Q.,Montgomery, John. "Combined Cyanoborylation, C-H Activation Strategy for Styrene Functionalization". . p. 8538 - 8543. Retrieved 2020/11/12.
• 2、 Xu, Hanhui,Ekoue-Kovi, Kekeli,Wolf, Christian. "Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents". . p. 7638 - 7650. Retrieved 2008/12/22.