6-Bromo-2,2'-bipyridine

Base Information

• Chemical Name: 6-Bromo-2,2'-bipyridine
• CAS No.: 10495-73-5
• Molecular Formula: C10H7BrN2
• Molecular Weight: 235.083
• Hs Code.: 2933399090
• Mol file: 10495-73-5.mol

Synonyms:2-Bromo-6-(2-pyridyl)pyridine;2,2'-Bipyridine,6-bromo-;6-Bromo-2,2'-bipyridyl;6-Bromo-[2,2']bipyridinyl;

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

Chemical Property:

• Melting Point: 72.0 to 76.0 °C
• Boiling Point: 328.59 °C at 760 mmHg
• PKA: 3.70±0.22(Predicted)
• Flash Point: 152.526 °C
• PSA: 25.78000
• Density: 1.494 g/cm³
• LogP: 2.90610
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform, Methanol

Purity/Quality:

99% ^*data from raw suppliers

6-Bromo-2,2’-bipyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6-Bromo-2,2’-bipyridine is a reagent used in the synthesis of electron transporting layers for OLEDs.

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

There total 20 articles about 6-Bromo-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: 93.0%

6-Chloro-[2,2']bipyridinyl (13040-77-2) → 2-bromo-6-(pyridin-2-yl)pyridine (10495-73-5)

Guidance literature:

With phosphorus tribromide; at 165 ℃; for 5h;

DOI:10.1139/v97-020

Reference yield: 88.0%

2,6-Dibromopyridine (626-05-1) + 2-tri-n-butylstannylpyridine (17997-47-6) → 2-bromo-6-(pyridin-2-yl)pyridine (10495-73-5)

Guidance literature:

2,6-Dibromopyridine; 2-tri-n-butylstannylpyridine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 15.5h; Reflux;

With ammonium hydroxide; In water; for 1.5h; Cooling with ice;

DOI:10.1021/ol703029d

Reference yield: 88.0%

6,6'-Dibromo-2,2'-bipyridine (49669-22-9) → 2-bromo-6-(pyridin-2-yl)pyridine (10495-73-5)

Guidance literature:

With phenyllithium; In tetrahydrofuran; diethyl ether; cyclohexane; at -85 - -80 ℃; for 1h;

upstream raw materials:

[2,2]bipyridinyl

2,6-Dibromopyridine

2-methylsulfinylpyridine

(+/-)-2-(ethylsulfinyl)pyridine

Downstream raw materials:

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

(2,2':6',2'':6'',2''':6''',2'''':6'''',2'''''-sexipyridine)

6-amino-2-2’-pyridylbipyridine

6-(4-bromophenyl)-2,2’-bipyridine

Refernces

• 1、 Uenishi,Tanaka,Wakabayashi,Oae,Tsukube. "Ipso substitution of 2-alkylsulfinylpyridine by 2-pyridyllithium; a new preparation of oligopyridine and their bromomethyl derivatives". . p. 4625 - 4628. Retrieved 1990.
• 2、 Brunner, Fabian,Graber, Stefan,Baumgartner, Yann,H?ussinger, Daniel,Prescimone, Alessandro,Constable, Edwin C.,Housecroft, Catherine E.. "The effects of introducing sterically demanding aryl substituents in [Cu(N^N)(P^P)]+ complexes". . p. 6379 - 6391. Retrieved 2017.
• 3、 Hammerland, Lance G.,Johansson, Martin,Malmstroem, Jonas,Mattsson, Jan P.,Minidis, Alexander B. E.,Nilsson, Karolina,Peterson, Alecia,Wensbo, David,Wallberg, Andreas,Oesterlund, Krister. "Structure-activity relationship of thiopyrimidines as mGluR5 antagonists". . p. 2467 - 2469. Retrieved 2006.
• 4、 Wang, Hongqiao,Wu, Nan,Zheng, Jing,Zheng, Chunyang,Wang, Dunjia. "Synthesis and structures of two mononuclear iron(ii) complexes derived from polypyridine ligands". . p. 100 - 102. Retrieved 2020.
• 5、 Boettger, Matthias,Wiegmann, Bjoern,Schaumburg, Steffen,Jones, Peter G.,Kowalsky, Wolfgang,Johannes, Hans-Hermann. "Synthesis of new pyrrole-pyridine-based ligands using an in situ Suzuki coupling method". . p. 1037 - 1047. Retrieved 2012.
• 6、 Parks,J.E. et al.. "-". . p. 53 - 66. Retrieved 1973.
• 7、 Duong, Vincent K.,Horan, Alexandra M.,McGarrigle, Eoghan M.. "Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines". . p. 8451 - 8457. Retrieved 2020/11/12.