4-Aminophthalic acid Chemical Properties

Melting point:

344 °C (dec.)(lit.)

Boiling point:

465.1±40.0 °C(Predicted)

Density 

1.551±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

3.41±0.10(Predicted)

color 

White to Gray to Brown

BRN 

2723405

InChI

InChI=1S/C8H7NO4/c9-4-1-2-5(7(10)11)6(3-4)8(12)13/h1-3H,9H2,(H,10,11)(H,12,13)

InChIKey

OXSANYRLJHSQEP-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=CC=C(N)C=C1C(O)=O

CAS DataBase Reference

5434-21-9(CAS DataBase Reference)

EPA Substance Registry System

4-Aminophthalic acid (5434-21-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Aminophthalic acid Usage And Synthesis

Chemical Properties

Beige powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of 4-amino phthalic acid from 4-nitrophthalic acid was as follows: 1 g (4.73 mmol) of 4-nitrophthalic acid was dissolved in 10 ml of anhydrous ethanol. The solution was stirred and degassed at room temperature and under argon protection. Subsequently, 50 mg of 5% palladium/carbon catalyst was added at once and hydrogen was passed into the solution for hydrogenation reaction. After 3 hours of reaction, the reaction mixture was filtered through diatomaceous earth to remove the catalyst. The filtrate was concentrated by evaporation to give an orange oily product with a mass of 820 mg and a yield of 96%. The structure of the product was confirmed by 1H NMR (DMSO-d6) with the following chemical shifts: 3.32 (1H, s), 5.95 (1H, s), 6.49-6.53 (2H, m), 7.46-7.50 (1H, d, J = 8.8 Hz), 12.33 (2H, COOH, s).

References

[1] Patent: US6689922, 2004, B1. Location in patent: Page column 20
[2] Patent: US6706725, 2004, B1. Location in patent: Page column 11
[3] Chemical Communications, 2017, vol. 53, # 62, p. 8751 - 8754
[4] Justus Liebigs Annalen der Chemie, 1881, vol. 208, p. 230
[5] Journal of the American Chemical Society, 1908, vol. 30, p. 1143

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