4-[(4-Methylphenyl)ethynyl]benzonitrile

Base Information

• Chemical Name: 4-[(4-Methylphenyl)ethynyl]benzonitrile
• CAS No.: 62856-06-8
• Molecular Formula: C16H11N
• Molecular Weight: 217.27
• DSSTox Substance ID: DTXSID60555804
• Nikkaji Number: J1.107.461H
• Wikidata: Q82437224
• Mol file: 62856-06-8.mol

Synonyms:62856-06-8;4-[(4-Methylphenyl)ethynyl]benzonitrile;4-p-Tolylethynyl-benzonitrile;4-(p-tolylethynyl)benzonitrile;SCHEMBL16104527;DTXSID60555804

Chemical Property of 4-[(4-Methylphenyl)ethynyl]benzonitrile

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 217.089149355
• Heavy Atom Count: 17
• Complexity: 345

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C#CC2=CC=C(C=C2)C#N

Technology Process of 4-[(4-Methylphenyl)ethynyl]benzonitrile

There total 19 articles about 4-[(4-Methylphenyl)ethynyl]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: 95.0%

4-bromobenzenecarbonitrile (623-00-7) + 4-n-methylphenylacetylene (766-97-2) → 4-[2-(4-methylphenyl)ethynyl]benzonitrile (62856-06-8)

Guidance literature:

With potassium phosphate; C₃₀H₃₇Br₂N₃Pd^(2-); In dimethyl sulfoxide; at 100 ℃; for 1h;

DOI:10.1016/j.tet.2013.04.061

Reference yield: 94.0%

4-iodobenzonitrile (3058-39-7) + 4-n-methylphenylacetylene (766-97-2) → 4-[2-(4-methylphenyl)ethynyl]benzonitrile (62856-06-8)

Guidance literature:

With thio-xanthene-9-one; N-isopropyl-N-tert-butylamine; nickel(II) acetate tetrahydrate; zinc trifluoromethanesulfonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Irradiation; Inert atmosphere;

DOI:10.1021/acs.joc.0c01177

Reference yield: 93.0%

4-cyanobenzenediazonium benzo[d][1,3,2]dithiazol-2-ide 1,1,3,3-tetraoxide + 4-n-methylphenylacetylene (766-97-2) → 4-[2-(4-methylphenyl)ethynyl]benzonitrile (62856-06-8)

Guidance literature:

With palladium diacetate; In dimethyl sulfoxide; at 20 ℃; for 0.0833333h; chemoselective reaction;

DOI:10.1002/ejoc.201301191

upstream raw materials:

4-iodobenzonitrile

4-n-methylphenylacetylene

2,2-dibromo-1-(4-cyanophenyl)ethene

tri(p-tolyl)bismuth

Downstream raw materials:

2-hydroxyethyl 4-cyanobenzoate

2-hydroxyethyl 4-methylbenzoate

4-[(E)-2-(4-Methylphenyl)ethen-1-yl]benzonitrile

Refernces

• 1、 Hajipour, Abdol R.,Malek, Shaghayegh Sadeghi. "Magnetic chitosan-functionalized cobalt-NHC: Synthesis, characterization and catalytic activity toward Suzuki and Sonogashira cross-coupling reactions of aryl chlorides". . . Retrieved 2021/04/23.
• 2、 -. "A transition metal catalytic nitro aromatic hydrocarbon with the end aryl alkyne cross-coupling for preparing aromatic of alkynes (by machine translation)". Paragraph 0027; 0054; 0056; 0057; 0058. . Retrieved 2018/10/19.