(2Z)-3-(4-Methylphenyl)-2-propenenitrile

Base Information

• Chemical Name: (2Z)-3-(4-Methylphenyl)-2-propenenitrile
• CAS No.: 35121-92-7
• Molecular Formula: C10H9N
• Molecular Weight: 143.188
• DSSTox Substance ID: DTXSID601273511
• Nikkaji Number: J2.582.736H
• Mol file: 35121-92-7.mol

Synonyms:SCHEMBL18532823;DTXSID601273511;35121-92-7;(2Z)-3-(4-Methylphenyl)-2-propenenitrile

Chemical Property of (2Z)-3-(4-Methylphenyl)-2-propenenitrile

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 143.073499291
• Heavy Atom Count: 11
• Complexity: 176

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C=CC#N
• Isomeric SMILES: CC1=CC=C(C=C1)/C=C\C#N

Technology Process of (2Z)-3-(4-Methylphenyl)-2-propenenitrile

There total 21 articles about (2Z)-3-(4-Methylphenyl)-2-propenenitrile 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: 57.0%

2-hydroxy-2-methylpropanenitrile (75-86-5) + (Z)-1-(2-iodovinyl)-4-methylbenzene → 3-(4-methylphenyl)-prop-2-enyl nitrile (35121-92-7)

Guidance literature:

With copper(l) iodide; 1,10-Phenanthroline; tributyl-amine; In N,N-dimethyl-formamide; at 110 ℃;

DOI:10.15227/orgsyn.093.0163

Reference yield: 56.0%

C22H28NO3P (1428990-72-0) + 4-methyl-benzaldehyde (104-87-0) → 3-(4-methylphenyl)-prop-2-enyl nitrile (35121-92-7)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 4h; stereoselective reaction;

DOI:10.1016/j.tetlet.2013.02.020

Reference yield: 41.0%

(cyanomethyl)triphenylphosphonium chloride (4336-70-3) + 4-methyl-benzaldehyde (104-87-0) → (E)-4-methylcinnamonitrile (28446-70-0) + 3-(4-methylphenyl)-prop-2-enyl nitrile (35121-92-7)

Guidance literature:

With sodium tetraphenyl borate; In acetonitrile; at 120 ℃; for 6h; Inert atmosphere;

DOI:10.1080/10426507.2014.902827

upstream raw materials:

2-cyano-3-(p-methylphenyl)propenoic acid

bis-trimethylsilanyl-acetonitrile

4-methyl-benzaldehyde

Trimethylsilylchloroacetonitrile

Downstream raw materials:

1-cyano-2-(4'-methylphenyl)ethane

cis-2,3-epoxy-3-(p-methylphenyl)propanenitrile