4-Bromo-2,2''-bipyridine Chemical Properties

Melting point:

52 °C

Boiling point:

325.2±27.0 °C(Predicted)

Density 

1.493

storage temp. 

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

form 

powder to crystal

pka

3.70±0.22(Predicted)

color 

White to Almost white

InChI

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

InChIKey

SCOXFIBXWCCICG-UHFFFAOYSA-N

SMILES

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

Safety Information

RIDADR 

UN2811

HazardClass 

6.1

HS Code 

2933399990

4-Bromo-2,2''-bipyridine Usage And Synthesis

Uses

4-bromo-2,2'-bipyridine is a useful research chemical.

Uses

4-Bromo-2,2'-bipyridine can be used as electro-active compounds in flow batteries.

Synthesis

Under nitrogen protection, 4-bromo-[2,2'-bipyridine] 1-oxide (786 mg, 3.13 mmol) was dissolved in dry chloroform (10 mL) and the solution was cooled to 0 °C. Subsequently, phosphorus tribromide (PBr3, 1.0 mL, 10 mmol) was slowly added to the solution. The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the mixture was poured into ice water, the pH was adjusted to alkaline with 6N aqueous sodium hydroxide and extracted with chloroform (CHCl3). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give the white solid product 4-bromo-2,2'-bipyridine (728 mg, 3.09 mmol, 98.7% yield). The structure of the product was confirmed by 1H NMR, IR spectroscopy, melting point and ESI-MS.1H NMR (CDCl3): δ = 8.69 (d, J = 5.0 Hz, 1H), 8.63 (d, J = 1.8 Hz, 1H), 8.49 (d, J = 5.1 Hz, 1H), 8.39 (d, J = 8.0 Hz, 1H), 7.83 ( dt, J1 = 8.0 Hz, J2 = 1.6 Hz, 1H), 7.48 (dd, J1 = 5.1 Hz, J2 = 1.8 Hz, 1H), 7.34 (ddd, J1 = 7.5 Hz, J2 = 4.8 Hz, J3 = 1.6 Hz, 1H). ir (kbr): ν = 1565, 1545, 1452, 1386, 1280, 1066, 994, 833 1066, 994, 833, 787, 687 cm-1. Melting point: 51.5-53 °C. ESI-MS: m/z = 256.9, 258.9 [M + Na]+ (calculated values C10H7N2Br + Na = 256.9, 258.9).

References

[1] Patent: US2012/247546, 2012, A1. Location in patent: Page/Page column 29
[2] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5514 - 5517
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 28, p. 6295 - 6302
[4] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 10, p. 2281 - 2288
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, # 8, p. 1293 - 1302

4-Bromo-2,2''-bipyridine(14162-95-9)Related Product Information

• 4-BROMOPYRIDINE
• 2-Bromopyridine
• 2-Amino-4-bromopyridine
• 2,2'-Bipyridine
• 5-BROMO-2,2'-BIPYRIDINE
• 4'-CHLORO-2,2':6',2''-TERPYRIDINE
• 2,2'-BIPYRIDINE-5-CARBOXYLIC ACID
• 2,2'-DIPYRIDYL N,N'-DIOXIDE
• 2,2':6',2''-TERPYRIDINE-4,4',4''-TRICARBOXYLIC ACID
• 4,4'-Dimethyl-2,2'-bipyridyl
• 4‘-(4-hydroxyphenyl)-2, 2':6‘, 2“-terpyridine
• 1,3,5-Tris(m-iodophenyl)benzene
• 4'-BROMO-2,2':6',2''-TERPYRIDINE
• 4-Methyl-4'-(3-carboxypropyl)-2,2'-bipyridine
• 6-BROMO-2,2'-BIPYRIDINE