6-BROMO-2,2'-BIPYRIDINE Chemical Properties

Melting point:

72.0 to 76.0 °C

Boiling point:

133°C/2.2mmHg(lit.)

Density 

1.493±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform, Methanol

form 

powder to crystal

pka

3.70±0.22(Predicted)

color 

White to Almost white

BRN 

130238

InChI

InChI=1S/C10H7BrN2/c11-10-6-3-5-9(13-10)8-4-1-2-7-12-8/h1-7H

InChIKey

NCRIDSGPLISUEU-UHFFFAOYSA-N

SMILES

C1(C2=NC=CC=C2)=NC(Br)=CC=C1

CAS DataBase Reference

10495-73-5

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

UN 2811

WGK Germany 

3

HazardClass 

6.1

HS Code 

2933399990

6-BROMO-2,2'-BIPYRIDINE Usage And Synthesis

Uses

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

Synthesis

General procedure for the synthesis of 6-bromo-2,2'-bipyridine from 2,6-dibromopyridine and 2-tributylmethylstannylpyridine: 1.5 g (6.33 mmol) of 2,6-dibromopyridine, 3.48 g (9.48 mmol) of 2-tributylmethylstannylpyridine and 0.15 g (0.06 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were were dissolved in 15 mL of toluene in a two-necked round bottom flask. The reaction mixture was stirred at 80°C for about 24 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. The resulting residue was dissolved in dichloromethane and subsequently extracted with 6M hydrochloric acid solution. The aqueous layer was separated and collected, the pH was adjusted by adding ammonia to the aqueous layer and extracted with dichloromethane. The organic layer was separated and dried with anhydrous magnesium sulfate (MgSO4) followed by evaporation under reduced pressure to remove the solvent. Purification by column chromatography (eluent: hexane/ethyl acetate=5:1, v/v) afforded 0.9 g of 6-bromo-2,2'-bipyridine as a white solid (yield: 61%).

References

[1] Organic Letters, 2008, vol. 10, # 6, p. 1091 - 1094
[2] Chemical Communications, 2007, # 42, p. 4401 - 4403
[3] Organometallics, 2017, vol. 36, # 9, p. 1727 - 1735
[4] Patent: KR2015/142709, 2015, A. Location in patent: Paragraph 0473-0475
[5] Inorganic Chemistry, 2013, vol. 52, # 9, p. 5570 - 5580

6-BROMO-2,2'-BIPYRIDINE(10495-73-5)Related Product Information

• 6,6'-DIBROMO-2,2'-DIPYRIDYL
• 5-BROMO-[2,3']-BIPYRIDINE
• 6-BROMO-2,2':6',2''-TERPYRIDINE
• 6,6-DIBROMO-2,2:6,2-TERPYRIDINE
• 6-BROMO-2,2'-BIPYRIDINE
• 6-BROMO-[2,2'-BIPYRIDINE]-4-CARBOXYLIC ACID
• 6-BROMO-4,4'-DIMETHYL-2,2'-BIPYRIDINE
• 5-BROMO-2,2'-BIPYRIDINE
• 6,6'-DIBROMO-4,4'-DIMETHYL-2,2'-BIPYRIDINE-1,1'-DI-OXIDE
• 6-BROMO-4-NITRO-2,2'-BIPYRIDINE
• 6-BROMO-4-METHOXY-2,2'-BIPYRIDINE
• 6-BROMO-4-N,N-DIMETHYLAMINO-2,2'-BIPYRIDINE
• 6-BROMO-2,2'-BIPYRIDINE-5-CARBOXALDEHYDE
• 6,6'-DIBROMO-4,4'-DIMETHYL-2,2'-BIPYRIDINE-1-OXIDE
• 6-BROMO-4-AZIDO-2,2'-BIPYRIDINE
• 6-BROMO-2,2'-BIPYRIDINE N-OXIDE
• 6'-BROMO-5-METHYL-2,2'-BIPYRIDINE
• 6-BROMO-4-METHYL-2,2'-BIPYRIDINE