3-AMINOPHTHALIC ACID HYDROCHLORIDE Chemical Properties

Melting point:

182 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Very Slightly)

form 

Crystalline Powder

color 

Off-white to yellow-beige

Stability:

Hygroscopic

InChI

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

InChIKey

ZBZAVEORKXFUQB-UHFFFAOYSA-N

SMILES

C1(C(=O)O)C(N)=CC=CC=1C(=O)O.Cl

CAS DataBase Reference

6946-22-1(CAS DataBase Reference)

EPA Substance Registry System

1,2-Benzenedicarboxylic acid, 3-amino-, hydrochloride (6946-22-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

24/25

TSCA 

Yes

HS Code 

29242998

MSDS

• Language:English Provider:ACROS

3-AMINOPHTHALIC ACID HYDROCHLORIDE Usage And Synthesis

Chemical Properties

off-white to yellow-beige crystalline powder

Uses

3-Aminophthalic Acid Hydrochloride is a reactant used in the preparation of local anesthetics.

Synthesis

The general procedure for the synthesis of 3-aminophthalic acid hydrochloride from 3-nitrophthalic acid was as follows: an ethanol solution (600 mL) of 3-nitrophthalic acid (100 g) and 10% Pd/C catalyst (3.2 g) was added to an autoclave. A hydrogen pressure of 4.0 kg was applied at 20-25 °C and the reaction was carried out for 3.0 hours. Upon completion of the reaction, the reaction mixture was cooled to 20 °C and filtered through a Hyflo bed. The filtrate was concentrated by distillation under reduced pressure and acetone was added to the residue. The mixture was cooled to 10 °C and concentrated hydrochloric acid was added slowly with continuous stirring. After removing the solvent under reduced pressure, acetonitrile was added. The mixture was again cooled to 10°C and the precipitated solid was filtered. Finally, the product was dried under vacuum at 45-50 °C for 6 h to give 3-aminophthalic acid hydrochloride (65.0 g).

References

[1] Patent: US5103057, 1992, A
[2] Patent: EP434145, 1991, A2
[3] Patent: WO2017/33116, 2017, A1. Location in patent: Paragraph 00114; 00132
[4] Patent: CN106986783, 2017, A. Location in patent: Paragraph 0008

3-AMINOPHTHALIC ACID HYDROCHLORIDE(6946-22-1)Related Product Information

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