6-Chloro-2,2'-bipyridine

Base Information

• Chemical Name: 6-Chloro-2,2'-bipyridine
• CAS No.: 13040-77-2
• Molecular Formula: C10H7ClN2
• Molecular Weight: 190.632
• Hs Code.: 2933399090
• European Community (EC) Number: 826-594-9
• DSSTox Substance ID: DTXSID30455781
• Nikkaji Number: J732.603C
• Wikidata: Q72517488
• Mol file: 13040-77-2.mol

Synonyms:6-CHLORO-2,2'-BIPYRIDINE;13040-77-2;2,2'-Bipyridine, 6-chloro-;2-chloro-6-pyridin-2-ylpyridine;6-Chloro-2,2/'-bipyridine;MFCD00216561;6-chlorobipyridine;2-chloro-6-(pyridin-2-yl)pyridine;SCHEMBL70338;6'-chloro-2,2'-bipyridine;AMY7436;DTXSID30455781;XRCUTZKABNKOEY-UHFFFAOYSA-N;BCP07548;AKOS006274959;CS-W004549;DS-6737;SY116376;FT-0761103;C72212;EN300-131005;A888744;6-Chloro-2,2 inverted exclamation mark -bipyridine;J-400784;Z1198152226

Chemical Property of 6-Chloro-2,2'-bipyridine

Chemical Property:

• Melting Point: 62℃
• Boiling Point: 320.628oC at 760 mmHg
• PKA: 3.72±0.22(Predicted)
• Flash Point: 177.279oC
• PSA: 25.78000
• Density: 1.245g/cm3
• LogP: 2.79700
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 190.0297759
• Heavy Atom Count: 13
• Complexity: 163

Purity/Quality:

99%, ^*data from raw suppliers

6-Chloro-2,2''-bipyridine ^*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(=CC=C2)Cl

Technology Process of 6-Chloro-2,2'-bipyridine

There total 20 articles about 6-Chloro-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%

2,6-dichloropyridine (2402-78-0) + 2-tri-n-butylstannylpyridine (17997-47-6) → 6-Chloro-[2,2']bipyridinyl (13040-77-2)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 11h; Reflux;

Reference yield: 91.0%

2-bromo-pyridine (109-04-6) + 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (652148-92-0) → 6-Chloro-[2,2']bipyridinyl (13040-77-2)

Guidance literature:

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine; In tetrahydrofuran; water; at 20 ℃; for 6h; Reagent/catalyst; chemoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.8b00257

Reference yield: 76.0%

1-methyl-2,2'-bipyridine-6-one (154928-15-1) → 6-Chloro-[2,2']bipyridinyl (13040-77-2)

Guidance literature:

With phosphorus pentachloride; trichlorophosphate; for 24h; Reflux;

DOI:10.1007/s11164-016-2426-x

upstream raw materials:

2,2'-bipyridyl N-oxide

(pyridin-2-yl)magnesium bromide

2-chloro-6-methylsulfinyl pyridine

<2,2'-bipyridin>-6(1H)-one

Downstream raw materials:

6-(diphenylphosphino)-2,2'-bipyridine

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

6-amino-2-2’-pyridylbipyridine

2-bromo-6-(pyridin-2-yl)pyridine

Refernces

• 1、 Kao, Hsien-Chang,Wang, Yi-Chun,Wang, Wen-Jwu. "Syntheses and crystal structures of two self-assembled dizinc(II) helicates with novel hydrazone linked polypyridyl ligands". . p. 3539 - 3552. Retrieved 2017.
• 2、 Chen, Chen,Chen, Mengjia,Meng, Haifang,Wang, Yani,Yang, Fang,Zhu, Bolin. "Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2′-bipyridine derivatives with sulfoxonium ylides". supporting information. p. 4268 - 4271. Retrieved 2021/05/31.
• 3、 -. "METHOD FOR COUPLING HALOGENATED PYRIDINE COMPOUND WITH HALOGENATED AROMATIC COMPOUND". Paragraph 0054; 0055. . Retrieved 2020/10/20.