(Z)-3-Phenylacrylonitrile

Base Information

• Chemical Name: (Z)-3-Phenylacrylonitrile
• CAS No.: 24840-05-9
• Molecular Formula: C9H7N
• Molecular Weight: 129.161
• DSSTox Substance ID: DTXSID601037159
• Nikkaji Number: J792.448H
• Mol file: 24840-05-9.mol

Synonyms:(Z)-3-Phenylacrylonitrile;24840-05-9;3-cis-phenyl-acrylonitrile;(Z)-3-phenyl-acrylonitrile;(2Z)-3-Phenylacrylonitrile;SCHEMBL996307;DTXSID601037159

Chemical Property of (Z)-3-Phenylacrylonitrile

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 129.057849228
• Heavy Atom Count: 10
• Complexity: 155

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (Z)-3-Phenylacrylonitrile

There total 125 articles about (Z)-3-Phenylacrylonitrile 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: 68.0%

iodobenzene (591-50-4) + acrylonitrile (107-13-1,25014-41-9) → cinnamic nitrile (1885-38-7) + (Z)-cinnamonitrile (24840-05-9) + dihydrocinnamonitrile (645-59-0)

Guidance literature:

With potassium carbonate; In water; at 60 - 70 ℃; for 24h; optical yield given as %de; chemoselective reaction;

DOI:10.1002/adsc.200900348

Reference yield: 55.0%

iodobenzene (591-50-4) + acrylonitrile (107-13-1,25014-41-9) → cinnamic nitrile (1885-38-7) + (Z)-cinnamonitrile (24840-05-9)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; at 100 ℃; for 8h; optical yield given as %de;

DOI:10.1016/j.tetlet.2011.05.006

Reference yield: 48.0%

acetonitrile (75-05-8,26809-02-9) + 4-nitro-N-(phenylmethylene)benzenamine (785-81-9,1613-94-1,40339-44-4) → cinnamic nitrile (1885-38-7) + (Z)-cinnamonitrile (24840-05-9) + 4-nitro-aniline (100-01-6,104810-17-5) + 3-(4-Nitro-phenylamino)-3-phenyl-propionitrile

Guidance literature:

With perhydrodibenzo-18-crown-6; for 1h;

DOI:10.1246/bcsj.59.3323

upstream raw materials:

pyridine

(E)-α-cyanocinnamic acid

benzaldehyde

cyanoacetic acid

Downstream raw materials:

(Z)-3-Phenyl-acrylimidic acid methyl ester; hydrochloride

(E)-3-phenylacrylic acid

(Z)-3-phenylacrylamide

dihydrocinnamonitrile

Refernces

• 1、 Andreou, Dimitrios,Essien, Nsikak B.,Pubill-Ulldemolins, Cristina,Terzidis, Michael A.,Papadopoulos, Athanasios N.,Kostakis, George E.,Lykakis, Ioannis N.. "Skeletally Tunable Seven-Membered-Ring Fused Pyrroles". supporting information. p. 6685 - 6690. Retrieved 2021/09/11.
• 2、 Inaba, Ryoto,Kawashima, Ikuo,Fujii, Toshiki,Yumura, Takashi,Imoto, Hiroaki,Naka, Kensuke. "Systematic Study on the Catalytic Arsa-Wittig Reaction". . p. 13400 - 13407. Retrieved 2020/09/21.