2,2'-Bipyridine-4,4'-dicarboxylic acid Chemical Properties

Melting point:

>310°C

Boiling point:

387.12°C (rough estimate)

Density 

1.3468 (rough estimate)

refractive index 

1.6360 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

1.67±0.10(Predicted)

form 

Powder

color 

White to white-gray

Water Solubility 

insoluble

BRN 

212894

InChI

InChI=1S/C12H8N2O4/c15-11(16)7-1-3-13-9(5-7)10-6-8(12(17)18)2-4-14-10/h1-6H,(H,15,16)(H,17,18)

InChIKey

FXPLCAKVOYHAJA-UHFFFAOYSA-N

SMILES

C1(C2=NC=CC(C(O)=O)=C2)=NC=CC(C(O)=O)=C1

CAS DataBase Reference

6813-38-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,2'-Bipyridine-4,4'-dicarboxylic acid Usage And Synthesis

Chemical Properties

white to white-grey powder

Uses

2,2'-Bipyridine-4,4'-dicarboxylic acid is used as an organic chemical synthesis intermediate.

Uses

2,2'-Bipyridine-4,4'-dicarboxylic acid can be used as an organic chemical synthesis intermediate

Synthesis

General procedure for the synthesis of 2,2'-bipyridine-4,4'-dicarboxylic acid from 4,4'-dimethyl-2,2'-bipyridine: 1.0 g (5.4 mmol) of 4,4'-dimethyl-2,2'-bipyridine was added to a reaction flask, and 18 mL of concentrated sulfuric acid was added slowly dropwise with stirring. This process was accompanied by a large amount of exothermic heat, and after the solution was cooled to room temperature, 3.3 g (11.3 mmol) of potassium dichromate was added, and the solution then changed to a dark green color. Subsequently, the reaction mixture was stirred at 65°C for 6 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction was poured into 1000 mL of water, which immediately produced a large white flocculent precipitate. The precipitate was collected by filtration and washed sequentially with water and methanol until the filtrate was clarified. Finally, the resulting white solid was dried under vacuum at 60 °C for 18 h to obtain the target product in 98% yield.

References

[1] Chemical Communications, 2010, vol. 46, # 13, p. 2197 - 2199
[2] Transition Metal Chemistry, 2011, vol. 36, # 8, p. 897 - 900
[3] Patent: CN107417737, 2017, A. Location in patent: Paragraph 0051-0054
[4] Helvetica Chimica Acta, 2018, vol. 101, # 5,
[5] Chemical Communications, 2006, # 1, p. 85 - 87

2,2'-Bipyridine-4,4'-dicarboxylic acid(6813-38-3)Related Product Information

• OXALIC ACID
• DIPIPERIDINOMETHANE
• 4,4'-Bipyridine
• 2-Picolinic acid
• Zinc picolinate
• Chromium picolinate
• Phthalic acid
• 2,2'-Bipyridine
• Bis(2-ethylhexyl) phthalate
• 2,2'-Bicinchoninic Acid
• 4,4'-Bis(ethoxycarbonly)-2,2'-bipyridine
• N719
• 2,2'-Bipyridine-4,4'-dicarboxylic acid dimethyl ester
• CIS-BIS(ISOTHIOCYANATO)BIS(2,2-BIPYRIDYL-4,4-DICARBOXYLATO)-RUTHENIUM(II)
• DIBUTYL 2,2'-BIPYRIDINE-4,4'-DICARBOXYLATE
• 2,2'-BIQUINOLINE-4,4'-DICARBOXYLIC ACID DIPOTASSIUM SALT TRIHYDRATE
• Bicinchoninic Acid Disodium Salt
• 2,2''-BIPYRIDINE-5,5''-DICARBOXYLIC ACID 97%