5-(Phenylethynyl)pyrimidine

Base Information

• Chemical Name: 5-(Phenylethynyl)pyrimidine
• CAS No.: 71418-88-7
• Molecular Formula: C12H8N2
• Molecular Weight: 180.20500
• UNII: LA7G57CJ2R
• DSSTox Substance ID: DTXSID50399052
• Nikkaji Number: J2.149.862I
• Wikidata: Q82201377
• ChEMBL ID: CHEMBL486244
• Mol file: 71418-88-7.mol

Synonyms:5-(phenylethynyl)pyrimidine;5-(2-phenylethynyl)pyrimidine;71418-88-7;CHEMBL486244;5-phenylethynylpyrimidine;D08PDF;LA7G57CJ2R;SCHEMBL4860070;DTXSID50399052;Pyrimidine, 5-(2-phenylethynyl)-;BDBM50243108;PD182425;SR-01000501737;SR-01000501737-1;F0919-2918;Z1255442925

Chemical Property of 5-(Phenylethynyl)pyrimidine

Chemical Property:

• Vapor Pressure: 0.000227mmHg at 25°C
• Boiling Point: 335.9oC at 760 mmHg
• Flash Point: 164.2oC
• PSA: 25.78000
• Density: 1.18g/cm3
• LogP: 1.87640
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 180.068748264
• Heavy Atom Count: 14
• Complexity: 223

Purity/Quality:

98% ^*data from raw suppliers

5-(Phenylethynyl)pyrimidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 5-(Phenylethynyl)pyrimidine

There total 6 articles about 5-(Phenylethynyl)pyrimidine 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: 96.0%

5-bromopyrimidine (4595-59-9) + phenylacetylene (536-74-3) → 5-(phenylethynyl)pyrimidine (71418-88-7)

Guidance literature:

With copper(l) iodide; 8-quinolinol; caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 24h; Inert atmosphere; Combinatorial reaction / High throughput screening (HTS);

DOI:10.1002/ejoc.200800394

Reference yield: 96.0%

phenylacetylene (536-74-3) + 5-iodopyrimidine (31462-58-5) → 5-(phenylethynyl)pyrimidine (71418-88-7)

Guidance literature:

With manganese; In ethanol; for 1.58333h; Reflux; Green chemistry;

DOI:10.1039/c8gc03919d

Reference yield: 88.0%

5-bromopyrimidine (4595-59-9) + phenylpropyolic acid (637-44-5) → 5-(phenylethynyl)pyrimidine (71418-88-7)

Guidance literature:

With C₁₈H₁₉N₃O₂Pd; caesium carbonate; In N,N-dimethyl-formamide; at 140 ℃; for 1h;

DOI:10.1002/adsc.201200876

upstream raw materials:

5-bromopyrimidine

phenylacetylene

1-Phenyl-2-(trimethylsilyl)acetylene

phenylpropyolic acid

Downstream raw materials:

5-(6,11-dibromo-1,3,4-triphenyltriphenylen-2-yl)pyrimidine

5-methyl-7-(pyrimidine-5-carbonyl)-5,6-dihydro-4H-dibenz[de,g]isoquinoline-4,6(5H)-dione

7-benzoyl-5-methyl-4H-isoquinolino[4,5-gh]quinazoline-4,6(5H)-dione

Refernces

• 1、 Cheng, Shen,Wei, Wei,Zhang, Xingyu,Yu, Hewei,Huang, Mingming,Kazemnejadi, Milad. "A new approach to large scale production of dimethyl sulfone: A promising and strong recyclable solvent for ligand-free Cu-catalyzed C-C cross-coupling reactions". . p. 2069 - 2076. Retrieved 2020/04/07.
• 2、 Sardarian, Ali Reza,Eslahi, Hassan,Esmaeilpour, Mohsen. "Green, cost-effective and efficient procedure for Heck and Sonogashira coupling reactions using palladium nanoparticles supported on functionalized Fe3O4@SiO2 by polyvinyl alcohol as a highly active, durable and reusable catalyst". . . Retrieved 2019/05/28.