beta-Phenylcrotononitrile

Base Information

• Chemical Name: beta-Phenylcrotononitrile
• CAS No.: 14368-40-2
• Molecular Formula: C10H9N
• Molecular Weight: 143.188
• NSC Number: 143537
• Nikkaji Number: J1.863.076A,J1.474.034A
• Mol file: 14368-40-2.mol

Synonyms:beta-Phenylcrotononitrile;(Z)-3-phenylbut-2-enenitrile;14368-40-2;2-Butenenitrile, 3-phenyl-, (2Z)-;14799-79-2;NSC143537;3-Phenyl-2-butenenitrile;SCHEMBL8548467;NSC-143537

Chemical Property of beta-Phenylcrotononitrile

Chemical Property:

• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: 1.543
• Boiling Point: 251.5 °C at 760 mmHg
• Flash Point: 105.9 °C
• Density: 0.996 g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 143.073499291
• Heavy Atom Count: 11
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of beta-Phenylcrotononitrile

There total 66 articles about beta-Phenylcrotononitrile 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%

(E)-3-phenyl-2-butenenitrile (14368-40-2,14799-79-2,14799-78-1) → (Z)-3-phenylbut-2-enenitrile (14368-40-2,14799-78-1,14799-79-2)

Guidance literature:

With copper diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In ethyl acetate; at 20 ℃; for 24h; Glovebox; Inert atmosphere; Irradiation; Sealed tube;

DOI:10.1021/acs.orglett.0c02894

Reference yield: 96.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + acetophenone (98-86-2) → 3-phenyl-2-butenonitrile (14368-40-2)

Guidance literature:

With sodium ethanolate; In ethanol; 1.) 1 h, room temp., 2.) 1 h, 60 deg C;

DOI:10.1248/cpb.28.1394

Reference yield: 95.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + acetophenone (98-86-2) → (E)-3-phenyl-2-butenenitrile (14368-40-2,14799-79-2,14799-78-1)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With sodium hydride; In diethyl ether; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

acetophenone; In diethyl ether; mineral oil; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.joc.8b02576

upstream raw materials:

chloroacetonitrile

acetophenone

cyanoacetic acid

cyanomethyl bromide

Downstream raw materials:

3-phenyl-butyronitrile

3-methyl-3-phenylglutaronitrile

1-amino-2-cyano-3,4-dimethyl-3,4-diphenylcyclopent-1-ene

(S)-3-phenylbutyronitrile

Refernces

• 1、 Yamamura,Murahashi. "". . p. 4429. Retrieved 1977.
• 2、 Ano, Yusuke,Higashino, Masaya,Yamada, Yuki,Chatani, Naoto. "Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones". . p. 3799 - 3802. Retrieved 2022/04/07.
• 3、 Cruché, Corentin,Neiderer, William,Collins, Shawn K.. "Heteroleptic Copper-Based Complexes for Energy-Transfer Processes: E → Z Isomerization and Tandem Photocatalytic Sequences". . p. 8829 - 8836. Retrieved 2021/07/28.