4,4'-BIS(DIHYDROXYPHOSPHORYL)-2,2'-BIPYRIDINE Chemical Properties

Boiling point:

741.1±70.0 °C(Predicted)

Density 

1.78±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

0.06±0.10(Predicted)

Appearance

Off-white to light yellow Solid

4,4'-BIS(DIHYDROXYPHOSPHORYL)-2,2'-BIPYRIDINE Usage And Synthesis

Uses

2,2'-Bipyridine-4,4'-bisphosphonic acid is an organic intermediate that can be used to prepare two-dimensional proton-conducting MOF materials, etc.

Synthesis

Diethyl 2,2'-bipyridine-4,4'-bisphosphonate (1.26 g, 2.94 mmol, 1.00 eq.) was dissolved in anhydrous dichloromethane under argon protection. To this solution was added bromotrimethylsilane (4.50 g, 29.4 mmol, 10.0 eq.), and the resulting yellow solution was stirred and reacted at room temperature for 24 hours. Upon completion of the reaction, methanol was slowly added dropwise until the color of the reaction mixture changed from yellow to colorless. Subsequently, extraction was carried out with water and 2,2'-bipyridine-4,4'-bisphosphonic acid (Compound 7) was isolated as a light yellow solid (0.93 g, 4.49 mmol, quantitative yield). The structure of the product was confirmed by nuclear magnetic resonance hydrogen (1H NMR, 400 MHz, DMSO-d6) and phosphorus spectra (31P NMR, 500 MHz, CDCl3): 1H NMR δ 8.85 (t, J = 4.5 Hz, 2H), 8.67 (d, J = 13.6 Hz, 2H), 7.73 (dd, J = 12.4, 4.8 Hz, 2H); 31P NMR δ 8.45 (s).

References

[1] Dyes and Pigments, 2014, vol. 104, p. 24 - 33
[2] Tetrahedron Letters, 1998, vol. 39, # 22, p. 3689 - 3692
[3] Inorganic Chemistry, 2015, vol. 54, # 2, p. 460 - 469

4,4'-BIS(DIHYDROXYPHOSPHORYL)-2,2'-BIPYRIDINE(194800-56-1)Related Product Information

• 2,2'-bipyridine-4-carboxylic acid
• 5,5'-Dibromo-2,2'-bipyridyl
• 4',4''''-(1,4-PHENYLENE)BIS(2,2':6',2''-TERPYRIDINE)
• 2,2'-Bipyridine-4,4'-dicarboxylic acid
• 4,4'-DIMETHOXY-2,2'-BIPYRIDINE
• 5,5'-DIMETHYL-2,2'-DIPYRIDYL
• 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine
• 6,6'-Dimethyl-2,2'-dipyridyl
• 2,2-bipyridine-6-carboxylic acid
• 4'-(9-Anthracenyl)-2,2':6',2''-terpyridine
• 2,6-BIS(2-PYRIDYL)-4(1H)-PYRIDONE
• 2,2':6',2''-TERPYRIDINE-4'-CARBALDEHYDE
• 4'-(4-BROMOPHENYL)-2,2':6',2''-TERPYRIDINE
• 2,2':6',2''-TERPYRIDINE
• 2,2':6',2''-TERPYRIDINE-4'-CARBOXYLIC ACID
• 4,4'-DIBROMO-2,2'-BIPYRIDINE
• 4,4'-BIS(DIHYDROXYPHOSPHORYL)-2,2'-BIPYRIDINE
• TETRAETHYL 2,2'-BIPYRIDINE-4,4'-BISPHOSPHONATE