2,2'-Bipyridine, 6,6'-bis[(trimethylsilyl)ethynyl]-

Base Information

• Chemical Name: 2,2'-Bipyridine, 6,6'-bis[(trimethylsilyl)ethynyl]-
• CAS No.: 133826-69-4
• Molecular Formula: C20H24N2Si2
• Molecular Weight: 348.595
• DSSTox Substance ID: DTXSID40444545
• Nikkaji Number: J772.096C
• Wikidata: Q82262711
• Mol file: 133826-69-4.mol

Synonyms:2,2'-Bipyridine, 6,6'-bis[(trimethylsilyl)ethynyl]-;133826-69-4;6,6'-Bis(trimethylsilylethynyl)-2,2'-bipyridine;DTXSID40444545

Chemical Property of 2,2'-Bipyridine, 6,6'-bis[(trimethylsilyl)ethynyl]-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 348.14780184
• Heavy Atom Count: 24
• Complexity: 506

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=NC(=CC=C1)C2=CC=CC(=N2)C#C[Si](C)(C)C

Technology Process of 2,2'-Bipyridine, 6,6'-bis[(trimethylsilyl)ethynyl]-

There total 1 articles about 2,2'-Bipyridine, 6,6'-bis[(trimethylsilyl)ethynyl]- 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: 63.0%

6,6'-Dibromo-2,2'-bipyridine (49669-22-9) + (trimethylsilylethynyl)tributyltin (81353-38-0) → 6,6′-bis((trimethylsilyl)ethynyl)-2,2′-bipyridine (133826-69-4)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 122 ℃; for 36h;

DOI:10.1002/1521-3765(20021115)8:22<5250::AID-CHEM5250>3.0.CO;2-Q

Reference yield: 79.0%

(1,2,3,4,5-pentamethylcyclopentadienyl)(1,2-bis(diphenylphosphino)ethane)iron(II)Cl + dichloromethane (75-09-2) + 6,6′-bis((trimethylsilyl)ethynyl)-2,2′-bipyridine (133826-69-4) → 6,6'-((dppe-κ2P,P')(η5-C5Me5)Fe(II)CC)2-2,2'-bipyridine*dichloromethane

Guidance literature:

With KF; KPF₆; KOC(CH₃)3; In tetrahydrofuran; methanol; (Ar); heating mixt. of iron compd., bipyridine deriv., KF and KPF6 in methanol/THF (3/1), stirring for 12 h at 20°C, addn. of potassium tert-butylate, stirring for 2 h; filtration, washing with methanol, CH2Cl2, and diethyl ether, drying in vac., elem. anal.;

DOI:10.1039/c1nj20269c

Reference yield:

6,6′-bis((trimethylsilyl)ethynyl)-2,2′-bipyridine (133826-69-4) → 6,6'-bis[(2-ethynylphenyl)ethynyl]-2,2'-bipyridine (501371-02-4)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. KOH / methanol; tetrahydrofuran / 20 h / 20 °C

2: 86 percent / CuI; Et₃N / [PdCl₂(dppf)]*CH₂Cl₂ / toluene / 192 h / 20 °C

3: 97 percent / aq. n-Bu₄NF / tetrahydrofuran / 18 h / 20 °C

With potassium hydroxide; copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; toluene; 2: Sonogashira reaction;

DOI:10.1002/1521-3765(20021115)8:22<5250::AID-CHEM5250>3.0.CO;2-Q

upstream raw materials:

6,6'-Dibromo-2,2'-bipyridine

(trimethylsilylethynyl)tributyltin

Downstream raw materials:

6,6'-bis[(2-ethynylphenyl)ethynyl]-2,2'-bipyridine

6,6'-bis[(2-trimethylsilylethynylphenyl)ethynyl]-2,2'-bipyridine

Refernces