1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID Chemical Properties

Melting point:

239 °C(Solv: methanol (67-56-1))

Boiling point:

563.1±45.0 °C(Predicted)

Density 

1.585±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

0.61±0.30(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C14H8N2O4/c17-13(18)9-5-3-7-1-2-8-4-6-10(14(19)20)16-12(8)11(7)15-9/h1-6H,(H,17,18)(H,19,20)

InChIKey

FXSVCROWUPWXBP-UHFFFAOYSA-N

SMILES

N1C2C(=CC=C3C=2N=C(C(O)=O)C=C3)C=CC=1C(O)=O

CAS DataBase Reference

57709-61-2

Safety Information

Risk Statements 

36/38

Safety Statements 

26

MSDS

• Language:English Provider:ALFA

1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID Usage And Synthesis

Uses

1,10-Phenanthroline-2,9-dicarboxylic acid hydrate is used to produce 1,10-phenanthroline-2,9-dicarbonyl chloride.

Synthesis

General procedure for the synthesis of 2,9-dicarboxy-1,10-phenanthroline from 2,9-bis(trichloromethyl)-1,10-phenanthroline: 2,9-bis(trichloromethyl)-1,10-phenanthroline (540 mg, 1.3 mmol, 1.0 eq.) was dissolved in a concentrated aqueous sulfuric acid solution (95-98%, 17 mL), and the reaction was stirred for 7 hr at 85 °C. Upon completion of the reaction, the brown reaction solution was cooled to room temperature and slowly poured onto crushed ice. After the ice was completely melted, the resulting white suspension was filtered under vacuum, washed thoroughly with water and dried in air to obtain the pure 2,9-dicarboxy-1,10-phenanthroline (360 mg, quantitative yield). The product characterization data were as follows: 1H NMR (300 MHz, DMSO-d6): δ= 8.22 (s, 2H), 8.42 (d, 3J = 8.4 Hz, 2H), 8.74 (d, 3J = 8.4 Hz, 2H); melting point 215-216 °C (decomposition).

References

[1] Synlett, 2018, vol. 29, # 10, p. 1362 - 1366
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1996, # 1, p. 75 - 82
[3] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 599 - 602

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