5-Ethynyl-2,2'-bipyridine

Base Information

• Chemical Name: 5-Ethynyl-2,2'-bipyridine
• CAS No.: 162318-34-5
• Molecular Formula: C12H8N2
• Molecular Weight: 180.209
• Hs Code.: 2933399090
• European Community (EC) Number: 874-935-5
• DSSTox Substance ID: DTXSID00440684
• Nikkaji Number: J967.052A
• Wikidata: Q82257054
• Mol file: 162318-34-5.mol

Synonyms:5-ETHYNYL-2,2'-BIPYRIDINE;162318-34-5;5-ethynyl-2-pyridin-2-ylpyridine;5-Ethynyl-2,2/'-bipyridine;2,2'-Bipyridine, 5-ethynyl-;SCHEMBL4075034;DTXSID00440684;MFCD27923087;AKOS022175056;DS-6512;CS-0091677;C73114;A882971

Chemical Property of 5-Ethynyl-2,2'-bipyridine

Chemical Property:

• Melting Point: 87-89 °C
• Boiling Point: 312.4±32.0 °C(Predicted)
• PKA: 3.74±0.22(Predicted)
• PSA: 25.78000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 2.12490
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 180.068748264
• Heavy Atom Count: 14
• Complexity: 228

Purity/Quality:

≥99% ^*data from raw suppliers

5-Ethynyl-2,2'-bipyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CN=C(C=C1)C2=CC=CC=N2

Technology Process of 5-Ethynyl-2,2'-bipyridine

There total 25 articles about 5-Ethynyl-2,2'-bipyridine 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: 99.0%

5-[(trimethylsilyl)ethynyl]-2,2'-bipyridine (187026-84-2) → 5-ethynyl-2,2'-bipyridine (162318-34-5)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 2h;

DOI:10.1039/c1cc15507e

Reference yield: 78.3%

5-bromo-2,2'-bipyridyl (15862-19-8) + trimethylsilylacetylene (1066-54-2) → 5-ethynyl-2,2'-bipyridine (162318-34-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; at 88 ℃; for 8h; Reflux; Inert atmosphere;

DOI:10.1039/c3dt32815e

Reference yield: 44.0%

5-(2,2-Dibromo-vinyl)-[2,2']bipyridinyl (204592-16-5) → 5-ethynyl-2,2'-bipyridine (162318-34-5)

Guidance literature:

With n-butyllithium; In hexane; at -60 ℃; for 2h;

DOI:10.1055/s-1998-2030

upstream raw materials:

5-[(trimethylsilyl)ethynyl]-2,2'-bipyridine

5-(2,2-Dibromo-vinyl)-[2,2']bipyridinyl

5-bromo-2,2'-bipyridyl

2-bromo-pyridine

Downstream raw materials:

1,4-bis(2',2-bipyridine-5-ylethinyl)-benzene

9-benzyl-8-[(2,2'-bipyridine-5-yl)ethynyl]adenine

[(η5-C5H5)(PPh3)2Ru=C=C(H)(2,2'-bipyridine-5-yl)]PF6

[(η5-C5H5)Fe(η5-C5H4PPh2)Au(CC-2,2'-bipyridyl-5-yl)]

Refernces

• 1、 Bunzen, Jens,Hapke, Marko,Luetzen, Arne. "The influence of different spacer lengths on the selectivity of self-assembly processes of bis(bipyridine)-BINOL helicates". . p. 3885 - 3894. Retrieved 2009.
• 2、 Benkh?user, Christian,Lützen, Arne. "Self-assembly of heteroleptic dinuclear metallosupramolecular kites from multivalent ligands via social self-sorting". . p. 693 - 700. Retrieved 2015.
• 3、 Lehr, Marc,McConnell, Anna J.,N?ther, Christian,Paschelke, Tobias,S?nnichsen, Frank D.,Trumpf, Eicke,Vogt, Anna-Marlene. "A Paramagnetic NMR Spectroscopy Toolbox for the Characterisation of Paramagnetic/Spin-Crossover Coordination Complexes and Metal–Organic Cages". supporting information. p. 19344 - 19351. Retrieved 2020/09/01.