2,2'-Bipyridine

Base Information

• Chemical Name: 2,2'-Bipyridine
• CAS No.: 366-18-7
• Molecular Formula: C10H8N2
• Molecular Weight: 157.195
• Hs Code.: 2933.39
• European Community (EC) Number: 206-674-4
• ICSC Number: 0093
• NSC Number: 615009,1550
• UNII: 551W113ZEP
• DSSTox Substance ID: DTXSID9040635
• Nikkaji Number: J46.972F,J2.457.336B,J2.457.337K
• Wikipedia: 2,2%E2%80%B2-Bipyridine
• Wikidata: Q209143
• Pharos Ligand ID: GQLBGMSYFK32
• Metabolomics Workbench ID: 54165
• ChEMBL ID: CHEMBL39879
• Mol file: 366-18-7.mol

Synonyms:2,2 Bipyridine;2,2 Bipyridyl;2,2 Dipyridyl;2,2' Bipyridine;2,2' Dipyridyl;2,2'-Bipyridine;2,2'-Dipyridyl;2,2-Bipyridine;2,2-Bipyridyl;2,2-Dipyridyl;alpha,alpha Dipyridyl;alpha,alpha-Dipyridyl;Bipyridyl;Dipyridyl, 2,2;Dipyridyl, 2,2'

Chemical Property of 2,2'-Bipyridine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.584Pa at 25℃
• Melting Point: 70-73 °C(lit.)
• Refractive Index: 1.4820 (estimate)
• Boiling Point: 272.499 °C at 760 mmHg
• PKA: pK1:-0.52(+2);pK2:4.352(+1) (20°C)
• Flash Point: 107.243 °C
• PSA: 25.78000
• Density: 1.106 g/cm³
• LogP: 2.14360
• Storage Temp.: Store at RT.
• Solubility.: 5.5g/l
• Water Solubility.: 5.5 g/L 22 ºC
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 156.068748264
• Heavy Atom Count: 12
• Complexity: 120

Purity/Quality:

98% ^*data from raw suppliers

2,2’-Dipyridyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38-20/21-23/24/25-21
• Safety Statements: 36/37-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)C2=CC=CC=N2
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Uses: A high-affinity chelator of iron. A reagent used for the determination of iron. 2,2'-bipyridine acts as a bidentate chelating ligand which form complexes with transition metal ions and shows antifungal, antibacterial and antiviral activity. It is used for the colorimetric determination of iron as well as oxidation reduction indicators to confirm the presence of ferrous ion in soils. It forms complexes with ruthenium and platinum, exhibit intense luminescence, which may have practical applications. Copper(I) bipyridine complexes involved in the oxidation of alcohols under aerobic conditions.

Technology Process of 2,2'-Bipyridine

There total 384 articles about 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: 100.0%

2-bromo-pyridine (109-04-6) → [2,2]bipyridinyl (366-18-7)

Guidance literature:

With palladium diacetate; potassium carbonate; In water; N,N-dimethyl-formamide; at 210 ℃; for 24h; Solvent; Reagent/catalyst; Catalytic behavior;

DOI:10.1039/c7nj02468a

Reference yield: 99.0%

2-iodopyridine (5029-67-4) → [2,2]bipyridinyl (366-18-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; johnphos; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 12h;

DOI:10.1021/jo010621q

Reference yield: 95.0%

[2,2']bipyridinyl 1,1'-dioxide (7275-43-6) → [2,2]bipyridinyl (366-18-7)

Guidance literature:

With titanium tetrachloride; tin(ll) chloride; In benzene; for 0.5h; Ambient temperature;

upstream raw materials:

pyridine

pyridine N-oxide

2-bromo-pyridine

2-iodopyridine

Downstream raw materials:

2,2':6,2''-terpyridine

2,2':6',2'':6'',2'''-quaterpyridine

6-bromo-2,2':6',2''-terpyridine

6-(o-N,N-dimethylaminophenyl)-2,2'-bipyridine

Refernces

• 1、 Yamamoto, Yutaka,Azuma, Yutaka,Mitoh, Hiroyuki. "General Method for Synthesis of Bipyridines: Palladium Catalyzed Cross-coupling Reaction of Trimethylstannylpyridines with Bromopyridines". . p. 564 - 565. Retrieved 1986.
• 2、 Parrish, Jay P.,Flanders, Vincent L.,Floyd, Ryan J.,Jung, Kyung Woon. "Mild and efficient formation of symmetric biaryls via Pd(II) catalysts and Cu(II) oxidants". . p. 7729 - 7731. Retrieved 2001.
• 3、 Brown,Ahmad. "-". . p. 3485,3487. Retrieved 1972.
• 4、 Mansour, Najwa,Mehanna, Stephanie,Mroueh, Mohamad A.,Audi, Hassib,Bodman-Smith, Kikki,Daher, Costantine F.,Taleb, Robin I.,El-Sibai, Mirvat,Khnayzer, Rony S.. "Photoactivatable RuII Complex Bearing 2,9-Diphenyl-1,10-phenanthroline: Unusual Photochemistry and Significant Potency on Cisplatin-Resistant Cell Lines". . p. 2524 - 2532. Retrieved 2018.
• 5、 Thorne,Rey,Denning,Watkins,Etchells,Green,Christou. "Excited state dynamics of organo-lanthanide electroluminescent phosphors: The properties of Tb(tb-pmp)3 and Gd(tb-pmp)3". . p. 4014 - 4021. Retrieved 2002.
• 6、 Leadbeater, Nicholas E.,Resouly, Sarah M.. "The use of Ni(CO)2(PPh3)2 in aryl and pyridyl coupling reactions". . p. 4243 - 4246. Retrieved 1999.
• 7、 Strukl, J. S.,Walter, J. L.. "". . p. 223 - 238. Retrieved 1971.
• 8、 -. "Novel synthesis method of 2, 2 '-dipyridyl". Paragraph 0017-0020. . Retrieved 2021/03/10.
• 9、 An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee. "Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents". supporting information. p. 2876 - 2894. Retrieved 2021/02/01.