| Identification | Back Directory | [Name]
Biphenyl-3,3',5,5'-tetracarboxylic acid | [CAS]
4371-28-2 | [Synonyms]
DK7232
DK7660
Biphenyl-3,3',5,5'-tetracarboxylicaci
3,3',5,5'-Biphenyltetracarboxylic acid
Biphenyl-3,3',5,5'-tetracarboxylic acid
Biphenyl-3,3',5,5'-tetracarboxylic Acid >
[1,1'-biphenyl]-3,3',5,5'-tetracarboxylicacid
5-(3,5-dicarboxyphenyl)benzene-1,3-dicarboxylic acid | [Molecular Formula]
C16H10O8 | [MDL Number]
MFCD16621475 | [MOL File]
4371-28-2.mol | [Molecular Weight]
330.246 |
| Chemical Properties | Back Directory | [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 | [form ]
solid | [pka]
3.06±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [Uses]
| [General Description]
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here. | [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 |
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