4-NITROISOPHTHALIC ACID Chemical Properties

Melting point:

258-259°C

Boiling point:

492.9±40.0 °C(Predicted)

Density 

1.671±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.86±0.25(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C8H5NO6/c10-7(11)4-1-2-6(9(14)15)5(3-4)8(12)13/h1-3H,(H,10,11)(H,12,13)

InChIKey

OCJFXVHDIVAONP-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=CC=C([N+]([O-])=O)C(C(O)=O)=C1

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-36

HazardClass 

IRRITANT

HS Code 

29173990

4-NITROISOPHTHALIC ACID Usage And Synthesis

Chemical Properties

Off-white powder

Synthesis

The general procedure for synthesizing 4-nitroisophthalic acid from 1,3-dimethyl-4-nitrobenzene was as follows: referring to Example 103, 1,3-dimethyl-4-nitrobenzene (10.0 g, 66.2 mmol) was dissolved in a mixed solvent of pyridine (65.0 mL) and water (130 mL), followed by batchwise addition of potassium permanganate (62.7 g, 0.397 mol) . The reaction mixture was stirred at room temperature for 30 min. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated by distillation under reduced pressure. The residue was acidified with 1N hydrochloric acid and subsequently extracted with ethyl acetate. After the extract was washed with water and dried with anhydrous magnesium sulfate, the solvent was removed by reduced pressure distillation to afford 4-nitroisophthalic acid (12.4 g, 89% yield) as yellow crystals. The obtained product could be directly used in the subsequent reaction without further purification.

References

[1] Patent: US6407116, 2002, B1
[2] Organic Letters, 2010, vol. 12, # 21, p. 4944 - 4947
[3] Patent: CN108164469, 2018, A. Location in patent: Paragraph 0094; 0095
[4] Tetrahedron, 1989, vol. 45, # 5, p. 1311 - 1322
[5] Patent: CN105384687, 2016, A. Location in patent: Paragraph 0394; 0395; 0396; 0397; 0398

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