[2,2'-Bipyridine]-5-carbonitrile

Base Information

• Chemical Name: [2,2'-Bipyridine]-5-carbonitrile
• CAS No.: 1802-28-4
• Molecular Formula: C₁₁H₇N₃
• Molecular Weight: 181.197
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID60462241
• Nikkaji Number: J1.782.624G
• Wikidata: Q82286742
• Mol file: 1802-28-4.mol

Synonyms:[2,2'-Bipyridine]-5-carbonitrile;1802-28-4;2,2'-BIPYRIDINE-5-CARBONITRILE;6-pyridin-2-ylpyridine-3-carbonitrile;2,2/'-BIPYRIDINE-5-CARBONITRILE;5-Cyano-2,2'-bipyridine;SCHEMBL2937466;PXIRMJXGWBMBHR-UHFFFAOYSA-;DTXSID60462241;[2,2/'-Bipyridine]-5-carbonitrile;AKOS006286950;CS-0203020;FT-0695504;J-400700;ETHYL2-(1-BENZYL-4-PIPERIDINYLIDENE)-2-CYANOACETATE;InChI=1/C11H7N3/c12-7-9-4-5-11(14-8-9)10-3-1-2-6-13-10/h1-6,8H

Chemical Property of [2,2'-Bipyridine]-5-carbonitrile

Chemical Property:

• Melting Point: 143-144 °C
• Boiling Point: 351.4±32.0 °C(Predicted)
• PKA: 3.26±0.22(Predicted)
• PSA: 49.57000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 2.01528
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 181.063997236
• Heavy Atom Count: 14
• Complexity: 230

Purity/Quality:

98%,99%, ^*data from raw suppliers

[2,2'-Bipyridine]-5-carbonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of [2,2'-Bipyridine]-5-carbonitrile

There total 5 articles about [2,2'-Bipyridine]-5-carbonitrile 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: 72.0%

5-bromo-2,2'-bipyridyl (15862-19-8) + sodium cyanide (143-33-9,25596-52-5) → (2,2'-bipyridine)-5-carbonitrile (1802-28-4)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; lead acetate; In 1,3,5-trimethyl-benzene; for 16h; Heating;

DOI:10.1055/s-2005-872113

Reference yield: 56.0%

2-(trimethylsilyl)pyridine (13737-04-7) + 2-bromo-5-cyanopyridine (139585-70-9) → (2,2'-bipyridine)-5-carbonitrile (1802-28-4)

Guidance literature:

With potassium fluoride; copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide; at 90 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02936

Reference yield: 55.0%

2-bromo-pyridine (109-04-6) + 6-chloronicotinonitrile (33252-28-7) → (2,2'-bipyridine)-5-carbonitrile (1802-28-4)

Guidance literature:

2-bromo-pyridine; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃;

With zinc(II) chloride; In tetrahydrofuran; pentane; at 20 ℃;

6-chloronicotinonitrile; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tri-tert-butyl phosphine; In tetrahydrofuran; pentane; for 16h; Heating;

DOI:10.1002/1099-0690(200207)2002:14<2292::AID-EJOC2292>3.0.CO;2-D

upstream raw materials:

2-bromo-pyridine

6-chloronicotinonitrile

5-bromo-2,2'-bipyridyl

sodium cyanide

Refernces

• 1、 Blakemore, David C.,Marples, Louise A.. "Palladium(0)-catalysed cross-coupling of 2-trimethylsilylpyridine with aryl halides". supporting information; experimental part. p. 4192 - 4195. Retrieved 2011/09/19.
• 2、 Luetzen, Arne,Hapke, Marko. "Synthesis of 5-substituted 2,2′-bipyridines from substituted 2-chloropyridines by a modified Negishi cross-coupling reaction". . p. 2292 - 2297. Retrieved 2007/10/03.