4,4'-DIAMINO-2,2'-BIPYRIDINE Chemical Properties

Melting point:

>270°C (dec.)

Boiling point:

521.0±50.0 °C(Predicted)

Density 

1.277±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

8.14±0.50(Predicted)

form 

Solid

color 

Off-White to Pale Green

InChI

InChI=1S/C10H10N4/c11-7-1-3-13-9(5-7)10-6-8(12)2-4-14-10/h1-6H,(H2,11,13)(H2,12,14)

InChIKey

WTHJTVKLMSJXEV-UHFFFAOYSA-N

SMILES

C1(C2=NC=CC(N)=C2)=NC=CC(N)=C1

Safety Information

Risk Statements 

20/21/22-36/38

Safety Statements 

20/21-51-36/37/39-44

HS Code 

29333990

4,4'-DIAMINO-2,2'-BIPYRIDINE Usage And Synthesis

Uses

4,4''-Diamino-2,2''-bipyridine is a bidendate chelator.

Synthesis

General procedure for the synthesis of 4,4'-diamino-2,2'-bipyridine N,N'-dioxide from 4,4'-dinitro-2,2'-bipyridine N,N'-dioxide: first, a 38 mL ethanol mixture containing 350 mg of 4,4'-dinitro-2,2'-bipyridine N,N'-dioxide and 630 mg Pd/C (5%) was purged with nitrogen. Subsequently, the suspension was heated to reflux under nitrogen protection. After the reactants were completely dissolved, 2.7 mL of a 10 mL ethanol solution of hydrazine hydrate was added slowly and dropwise over a period of 20 min. The reaction mixture was kept at reflux for 15 hours. Immediately after completion of the reaction, the mixture was filtered under reduced pressure and washed with boiling ethanol. After solvent removal, the resulting yellow precipitate was ground in 20 mL of water and allowed to stand overnight at 2°C. The white solid was isolated by vacuum filtration, washed with cold water and dried at 50 °C. A final 195 mg of white powdery product was obtained in 83% yield.

References

[1] Chemical Communications, 1999, # 24, p. 2521 - 2522
[2] New Journal of Chemistry, 2001, vol. 25, # 12, p. 1553 - 1566
[3] RSC Advances, 2016, vol. 6, # 20, p. 16482 - 16488
[4] European Journal of Inorganic Chemistry, 2014, vol. 2014, # 31, p. 5322 - 5330
[5] Dalton Transactions, 2004, # 24, p. 4130 - 4138

4,4'-DIAMINO-2,2'-BIPYRIDINE(18511-69-8)Related Product Information

• 4,4'-DIBROMO-2,2'-BIPYRIDINE
• 2,2'-bipyridin-4-amine
• 4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl
• 4,4'-diethynyl-2,2'-bipyridine
• 4,4'-DICHLORO-2,2'-BIPYRIDINE
• 5,5'-bis-ethynyl-2,2'-bipyridine
• 2,2'-Bipyridine, 4,4'-bis[(trimethylsilyl)ethynyl]-
• 4-ethynyl-2,2'-bipyridine
• 5-[(trimethylsilyl)ethynyl]-2,2'-bipyridine
• 5-Ethynyl-2,2'-bipyridine
• 4-[2-(trimethylsilyl)ethynyl]-2,2'-bipyridine
• 4-chloro-2,2'-bipyridine
• 4-chloro-4'-nitro-2,2'-bipyridine
• 5,5'-bis[2-(trimethylsilyl)ethynyl]-2,2'-bipyridine
• 4,4'-DICYANO-2,2'-BIPYRIDINE
• 4,4'-DINITRO-2,2'-BIPYRIDINE
• 4,4'-DIAMINO-2,2'-BIPYRIDINE
• 4,4-dinitro-2,2-bipyridine N,N-dioxide