2,3'-Bipyridine

Base Information

• Chemical Name: 2,3'-Bipyridine
• CAS No.: 581-50-0
• Molecular Formula: C10H8N2
• Molecular Weight: 156.187
• Hs Code.: 2933399090
• European Community (EC) Number: 209-468-2
• UNII: WG6152JUQT
• DSSTox Substance ID: DTXSID00206823
• Nikkaji Number: J134.762D
• Wikidata: Q209171
• ChEMBL ID: CHEMBL178348
• Mol file: 581-50-0.mol

Synonyms:2,3'-BIPYRIDINE;581-50-0;Isonicoteine;2,3'-Dipyridyl;2,3'-Bipyridyl;2,3'-Dipyridine;[2,3']Bipyridinyl;2-pyridin-3-ylpyridine;alpha,beta-Dipyridyl;alpha,beta'-Bipyridine;2-(pyridin-3-yl)pyridine;CCRIS 2364;2-(3-pyridyl)pyridine;UNII-WG6152JUQT;EINECS 209-468-2;WG6152JUQT;.alpha.,.beta.-Dipyridyl;CHEMBL178348;3-(2-PYRIDYL)PYRIDINE;2-(3-PYRIDINYL)PYRIDINE;DTXSID00206823;MFCD00006215;2,3-bipyridine;2,3'-Bipyridinyl;2,3-Dipyridyl;2,3/'-Bipyridine;[2,3'']Bipyridinyl;alpha,beta-BIPYRIDINE;[2,3'''']Bipyridinyl;.alpha.,.beta.'-Bipyridine;SCHEMBL998601;DTXCID30129314;.ALPHA.,.BETA.-BIPYRIDINE;AB9962;BDBM50158948;AKOS006281711;CS-W019058;DS-13607;LS-44604;US8609708, 66 2,3'-Bipyridyl;A8251;D1772;FT-0603480;EN300-76175;Q209171;Z1187786372

Chemical Property of 2,3'-Bipyridine

Chemical Property:

• Appearance/Colour: pale yellow oil
• Vapor Pressure: 0.00271mmHg at 25°C
• Melting Point: 30-32 °C(Solv: ligroine (8032-32-4))
• Refractive Index: 1.58
• Boiling Point: 295.3 °C at 760 mmHg
• PKA: pK1:1.52(+2);pK2:4.42(+1) (20°C)
• Flash Point: 111.4 °C
• PSA: 25.78000
• Density: 1.106g/cm³
• LogP: 2.14360
• Storage Temp.: -20°C Freezer
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 156.068748264
• Heavy Atom Count: 12
• Complexity: 136

Purity/Quality:

99%, ^*data from raw suppliers

Isonicoteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)C2=CN=CC=C2
• Description: This alkaloid, obtained by Noga from Turkish Nicotiana species, is obtained as a colourless, viscous oil which is optically inactive and has D~~o 1.0984. It is freely soluble in most organic solvents but only slightly so in H2 0 or light petroleum. The structure has been shown to be 2:3'-dipyridyL

Technology Process of 2,3'-Bipyridine

There total 106 articles about 2,3'-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: 98.0%

2-chloropyridine (109-09-1) + 3-pyridylboronic acid (1692-25-7) → 2,3'-bipyridine (581-50-0)

Guidance literature:

With potassium phosphate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tricyclohexylphosphine; In 1,4-dioxane; water; at 100 ℃; for 18h;

DOI:10.1002/anie.200503479

Reference yield: 95.0%

2-bromo-pyridine (109-04-6) + 3-pyridylboronic acid (1692-25-7) → 2,3'-bipyridine (581-50-0)

Guidance literature:

With C₁₈H₂₀Cl₂N₈Pd; caesium carbonate; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1007/s11243-012-9598-z

Reference yield: 91.0%

2-(phenylsulfonyl)pyridine (24244-60-8) → 2,3'-bipyridine (581-50-0)

Guidance literature:

3-Bromopyridine; With isopropylmagnesium chloride; In tetrahydrofuran; for 1.16667h;

2-(phenylsulfonyl)pyridine; In tetrahydrofuran; at 20 ℃; for 5.16667h;

upstream raw materials:

3-Aminomethylpyridine

[2,3']bipyridyl-3,2'-dicarboxylic acid

anatabine

(+/-)-Anatabine

Downstream raw materials:

nicotinic acid

1'-(2-(4-nitrophenyl)ethyl)-2,3'-bipyridinium iodide

m-chlorophenyl phenylsulfide

1-Chloro-3-phenylsulfanyl-benzene

Refernces

• 1、 Andrud, Kristin,Xing, Hong,Gabrielsen, Bjarne,Bloom, Linda,Mahnir, Vladimir,Lee, Stephen,Green, Benedict T.,Lindstrom, Jon,Kem, William. "Investigation of the possible pharmacologically active forms of the nicotinic acetylcholine receptor agonist anabaseine". . . Retrieved 2019.
• 2、 Kurbatov,Zalyalieva. "-". . . Retrieved 1977.
• 3、 Aksenov,Aksenova,Malikova,Shcherbakov,Zhirov. "Reaction of vinylpyridines and vinylquinolines with 1,3,5-triazine in polyphosphoric acid". . p. 1740 - 1741. Retrieved 2009.
• 4、 Aksenov,Aksenova,Malikova,Aksenov. "Synthesis of bipyridyls by the reaction of allylpyridines with 1,3,5-triazine in polyphosphoric acid". . p. 254 - 255. Retrieved 2009.
• 5、 Hishitani, Shinichiro,Naniwa, Shimpei,Yamamoto, Akira,Yoshida, Hisao. "Ligand-to-metal charge transfer of a pyridine surface complex on TiO2for selective dehydrogenative cross-coupling with benzene". . p. 11366 - 11373. Retrieved 2021/05/31.
• 6、 Horan, Alexandra M.,Duong, Vincent K.,McGarrigle, Eoghan M.. "Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts". supporting information. p. 9089 - 9093. Retrieved 2021/11/30.