4-AMINO-5-CHLORO-2-METHOXYBENZOIC ACID Chemical Properties

Melting point:

206 °C (dec.) (lit.)

Boiling point:

369.7±42.0 °C(Predicted)

Density 

1.3639 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Powder

pka

4.38±0.10(Predicted)

color 

White to slightly beige

InChI

InChI=1S/C8H8ClNO3/c1-13-7-3-6(10)5(9)2-4(7)8(11)12/h2-3H,10H2,1H3,(H,11,12)

InChIKey

RVEATKYEARPWRE-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(Cl)=C(N)C=C1OC

CAS DataBase Reference

7206-70-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29225090

MSDS

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

4-AMINO-5-CHLORO-2-METHOXYBENZOIC ACID Usage And Synthesis

Chemical Properties

WHITE TO SLIGHTLY BEIGE POWDER

Uses

4-Amino-5-chloro-2-methoxybenzoic Acid (Metoclopramide EP Impurity C) is a Metoclopramide (M338685) metabolite.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of 4-amino-5-chloro-2-methoxybenzoic acid using methyl 4-amino-5-chloro-2-methoxybenzoate as the raw material was as follows: (3) The above obtained methyl 4-amino-5-chloro-2-methoxybenzoate was mixed with potassium hydroxide at a molar ratio of 1:2.2, and stirred at reflux in a solvent mixture of 7 liters of methanol and water (in a ratio of 5:2, v/v) for more than 2 hours. Activated carbon was then added for decolorization and refluxing was continued for 30 minutes. After completion of the reaction, the activated carbon was removed by filtration. The filtrate was concentrated on a rotary evaporator to remove most of the solvent and then diluted by adding water. The pH was slowly adjusted to 5 with a 3 mol/L hydrochloric acid solution, at which point a white solid precipitated from the aqueous solution. The solid product was collected by filtration and dried to give 1.93 kg of 4-amino-5-chloro-2-methoxybenzoic acid in 91.4% yield. The structure of the product can be confirmed by hydrogen spectroscopy (Figure 1).

References

[1] Patent: CN105237422, 2016, A. Location in patent: Paragraph 0018; 0022
[2] Organic Preparations and Procedures International, 1992, vol. 24, # 1, p. 64 - 66
[3] Journal of Molecular Structure, 1988, vol. 172, p. 381 - 394

4-AMINO-5-CHLORO-2-METHOXYBENZOIC ACID(7206-70-4)Related Product Information

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