4-HYDROXYPHTHALIC ANHYDRIDE Chemical Properties

Melting point:

171-173 °C(Solv: acetic acid (64-19-7))

Boiling point:

407.8±28.0 °C(Predicted)

Density 

1.624±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

6.52±0.20(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C8H4O4/c9-4-1-2-5-6(3-4)8(11)12-7(5)10/h1-3,9H

InChIKey

PXHIYFMTRHEUHZ-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=C(O)C=C2)C(=O)O1

4-HYDROXYPHTHALIC ANHYDRIDE Usage And Synthesis

Uses

4-Hydroxyphthalic anhydride is a derivative of 3-hydroxyphthalic anhydride and can be used to modify proteins for in vitro biologics studies.

Synthesis

The sublimation reaction was carried out at 220 °C and under vacuum conditions (~10 mbar) using 4-hydroxyphthalic acid (1 g, 5.49 mmol) as the raw material. Upon completion of the reaction, the resulting white solid 5-hydroxyisobenzofuran-1,3-dione (675 mg, 4.11 mmol, 74.9% yield, MS/ESI+ 164.9 [MH]+) was collected. The product is to be stored under vacuum and used directly in subsequent reaction steps.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4427 - 4431
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 342 - 353
[3] Patent: CN104910113, 2017, B. Location in patent: Page/Page column 0041; 0044-0046
[4] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
[5] Patent: US2013/102576, 2013, A1. Location in patent: Paragraph 0607

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