3-[(E)-2-Phenylethenyl]benzonitrile

Base Information

• Chemical Name: 3-[(E)-2-Phenylethenyl]benzonitrile
• CAS No.: 14064-35-8
• Molecular Formula: C15H11N
• Molecular Weight: 205.259
• Hs Code.: 2926909090
• Nikkaji Number: J145.985F,J303.356B
• ChEMBL ID: CHEMBL4093517
• Mol file: 14064-35-8.mol

Synonyms:3-[(E)-2-Phenylethenyl]benzonitrile;3-Stilbenecarbonitrile, (E)-;trans-o-Cyanostilbene;14064-35-8;Benzonitrile, 3-(2-phenylethenyl)-, (E)-;3-([e]-2-Phenylethenyl)benzonitrile;3-cyanostilbene;SCHEMBL1405480;CHEMBL4093517;CWLWKFGHSCEUQB-MDZDMXLPSA-N;3-[(E)-2-Phenylethenyl]benzonitrile #

Chemical Property of 3-[(E)-2-Phenylethenyl]benzonitrile

Chemical Property:

• PSA: 23.79000
• LogP: 3.72868
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 205.089149355
• Heavy Atom Count: 16
• Complexity: 277

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC2=CC(=CC=C2)C#N
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C2=CC(=CC=C2)C#N

Technology Process of 3-[(E)-2-Phenylethenyl]benzonitrile

There total 14 articles about 3-[(E)-2-Phenylethenyl]benzonitrile 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: 99.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 3-chloro-benzonitrile (766-84-7) → (E)-3-styrylbenzonitrile (14064-35-8)

Guidance literature:

With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC⁴]tetrapalladium; tetrabutylammomium bromide; sodium acetate; at 140 ℃; for 16h;

DOI:10.1002/adsc.201900805

Reference yield: 97.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 3-cyanobromobenzene (6952-59-6) → (E)-3-styrylbenzonitrile (14064-35-8)

Guidance literature:

With phenyl carbamate; potassium carbonate; palladium diacetate; In N,N-dimethyl-formamide; at 130 ℃; for 2h;

DOI:10.1016/j.tetlet.2006.10.124

Reference yield: 82.0%

3-cyanobromobenzene (6952-59-6) + trans-2-phenylvinylboronic acid (6783-05-7) → (E)-3-styrylbenzonitrile (14064-35-8)

Guidance literature:

With 2H⁽¹⁺⁾*Cl₄Pd^(2-)*2H₃N; poly[N-isopropylacrylamide-co-diphenyl(4'-styryl)phosphine]; sodium carbonate; In water; at 100 ℃; for 6h;

DOI:10.1021/jo034354v

upstream raw materials:

3-Cyanobenzaldehyde

benzylchlorotriphenylphosphorane

3-[(1,1,1-triphenylphosphonio)methyl]benzonitrile bromide

benzaldehyde

Downstream raw materials:

Trans-3-(1'hydroxyhexyl) Stilbene

trans-3-hexanoylstilbene

Refernces

• 1、 Hung, Cheng-Hau,Zheng, Wei-Yuan,Lee, Hon Man. "Palladium Complexes with Phenoxy- And Amidate-Functionalized N-Heterocyclic Carbene Ligands Based on 3-Phenylimidazo[1,5- a]pyridine: Synthesis and Catalytic Application in Mizoroki-Heck Coupling Reactions with Ortho-Substituted Aryl Chlorides". . p. 702 - 713. Retrieved 2021/04/02.
• 2、 Yang, Qiang,Sane, Neeraj,Klosowski, Daniel,Lee, Melissa,Rosenthal, Tay,Wang, Nick X.,Wiensch, Eric. "Mizoroki-Heck Cross-Coupling of Bromobenzenes with Styrenes: Another Example of Pd-Catalyzed Cross-Coupling with Potential Safety Hazards". . p. 2148 - 2156. Retrieved 2019/11/02.