Biphenyl-3,3',5,5'-tetracarboxylic acid Chemical Properties

Melting point:

>400℃

Boiling point:

772.3±60.0 °C(Predicted)

Density 

1.612±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.06±0.10(Predicted)

form 

solid

color 

White to Almost white

InChI

InChI=1S/C16H10O8/c17-13(18)9-1-7(2-10(5-9)14(19)20)8-3-11(15(21)22)6-12(4-8)16(23)24/h1-6H,(H,17,18)(H,19,20)(H,21,22)(H,23,24)

InChIKey

QURGMSIQFRADOZ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

N

Risk Statements 

50

Safety Statements 

61

RIDADR 

UN 3077

WGK Germany 

3

HS Code 

29173990

Biphenyl-3,3',5,5'-tetracarboxylic acid Usage And Synthesis

Uses

Selected Applications of MOFs in Sustainable Energy Technologies

General Description

This product has been enhanced for energy efficiency.

Synthesis

A mixture of 3,3',5,5'-tetrakis(methoxycarbonyl)biphenyl (12) (0.96 g, 2.5 mmol) was dissolved in water (40 mL) with THF (40 mL) and NaOH (1.6 g, 40 mmol) and reacted at reflux for 1 hour. Subsequently, the organic solvent was evaporated under reduced pressure and the remaining aqueous solution was continued to reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled and acidified with 50% H2SO4 until the precipitation was complete. The precipitate was collected by filtration and dried to give the target product 3,3',5,5'-biphenyltetracarboxylic acid (9) as a white powder in 89% yield. Product melting point > 350°C. 1H-NMR (400 MHz, DMSO-d6): δ = 8.44 (d, 4H, J = 1.5 Hz), 8.53 (t, 2H, J = 1.5 Hz), 13.48 (bs, 4H). 13C-NMR (100 MHz, DMSO-d6): δ = 129.5, 131.4, 132.3 , 139.2, 166.3. MS-EI, m/z (%): 330 (100) [M+], 313 (40), 285 (15), 240 (5).

References

[1] Journal of Organic Chemistry, 2006, vol. 71, # 20, p. 7854 - 7857
[2] European Journal of Organic Chemistry, 2007, # 20, p. 3271 - 3276
[3] Patent: EP1972338, 2008, A1. Location in patent: Page/Page column 14
[4] Journal of the Chemical Society, 1923, vol. 123, p. 1045

Biphenyl-3,3',5,5'-tetracarboxylic acid(4371-28-2)Related Product Information

• 3,7-dibromo-10H-phenothiazine
• 1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE
• biphenyl-3,3',5,5'-tetracarbaldehyde
• Biphenyl-4,4'-dicarboxylic acid
• Biphenyl-4,4'-dithiol
• Biphenyl-3,4′,5-tricarboxylic acid
• BIFENAZATE
• Oleic acid