1,10-Phenanthroline, 3,8-bis(phenylethynyl)-

Base Information

• Chemical Name: 1,10-Phenanthroline, 3,8-bis(phenylethynyl)-
• CAS No.: 168003-69-8
• Molecular Formula: C28H16N2
• Molecular Weight: 380.448
• DSSTox Substance ID: DTXSID10478115
• Nikkaji Number: J1.195.220H
• Wikidata: Q82311305
• Mol file: 168003-69-8.mol

Synonyms:3,8-Bis(phenylethynyl)-1,10-phenanthroline;168003-69-8;1,10-Phenanthroline, 3,8-bis(phenylethynyl)-;3,8-BIS(2-PHENYLETHYNYL)-1,10-PHENANTHROLINE;DTXSID10478115;MFCD32642928;F74298

Chemical Property of 1,10-Phenanthroline, 3,8-bis(phenylethynyl)-

Chemical Property:

• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 380.131348519
• Heavy Atom Count: 30
• Complexity: 640

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#CC2=CN=C3C(=C2)C=CC4=CC(=CN=C43)C#CC5=CC=CC=C5

Technology Process of 1,10-Phenanthroline, 3,8-bis(phenylethynyl)-

There total 2 articles about 1,10-Phenanthroline, 3,8-bis(phenylethynyl)- 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: 90.0%

3,8-dibromo-1,10-phenathroline (100125-12-0) + phenylacetylene (536-74-3) → 3,8-bis(phenylacetylene)-1,10-phenanthroline (168003-69-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In methanol; for 4h; Ambient temperature;

DOI:10.1016/0040-4039(95)01190-S

Reference yield:

3,8-dibromo-1,10-phenathroline (100125-12-0) + tributylstannylethynylbenzene (3757-88-8) → 3,8-bis(phenylacetylene)-1,10-phenanthroline (168003-69-8)

Guidance literature:

3,8-dibromo-1,10-phenathroline; tributylstannylethynylbenzene; Pd(PPh₃); In 1,4-dioxane; at 110 ℃;

With potassium fluoride; In diethyl ether; at 20 ℃;

DOI:10.1002/adsc.200404233

Reference yield: 71.0%

ammonium hexafluorophosphate + bis(4,4'-di-tert-butyl-2,2'-bipyridine)-ruthenium(II)-dichloride + 3,8-bis(phenylacetylene)-1,10-phenanthroline (168003-69-8) → bis(4,4'-di-tert-butyl-2,2'-bipyridine)(3,8-bis(phenylacetylene)-1,10-phenanthroline)ruthenium(II) hexafluorophosphate monohydrate

Guidance literature:

In ethanol; water; other Radiation; (Ar or N2), Ru complex and ligand (1:1) suspnd. on EtOH/H2O 5:3 v/v, refluxed for 2 h under microwave irradiation, cooled to room temp., filtered, concd., pptd. with aq.NH4PF6; filtered, washed (h2O, EtOH, Et2O), dried (air);

DOI:10.1002/ejic.200900310

upstream raw materials:

3,8-dibromo-1,10-phenathroline

phenylacetylene

tributylstannylethynylbenzene

Refernces

• 1、 Karnahl, Michael,Krieck, Sven,Goerls, Helmar,Tschierlei, Stefanie,Schmitt, Michael,Popp, Juergen,Chartrand, Daniel,Hanan, Garry S.,Groarke, Robert,Vos, Johannes G.,Rau, Sven. "Synthesis and photophysical properties of 3,8-disubstituted 1,10-phenanthrolines and their ruthenium (II) complexes". experimental part. p. 4962 - 4971. Retrieved 2010/05/01.