3-Amino-4-chlorobenzoic acid Chemical Properties

Melting point:

214-215 °C (lit.)

Boiling point:

250°C (rough estimate)

Density 

1.3246 (rough estimate)

vapor pressure 

0.001Pa at 25℃

refractive index 

1.5560 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Powder

pka

4.13±0.10(Predicted)

color 

Light beige to beige

BRN 

2085846

InChIKey

DMGFVJVLVZOSOE-UHFFFAOYSA-N

LogP

1.6 at 25℃

Dissociation constant

2.7-2.9 at 25℃

CAS DataBase Reference

2840-28-0(CAS DataBase Reference)

NIST Chemistry Reference

3-Amino-4-chlorobenzoic acid(2840-28-0)

EPA Substance Registry System

Benzoic acid, 3-amino-4-chloro- (2840-28-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

TSCA 

Yes

HS Code 

29224995

MSDS

• Language:English Provider:4-Chloro-3-aminobenzoic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Amino-4-chlorobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Amino-4-chlorobenzoic Acid is a useful reagent for preparation of novel bis-triazolyl-aryl-benzimidazole-thiol derivatives.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 3-amino-4-chlorobenzoic acid from methyl 3-amino-4-chlorobenzoate: to a stirred solution of methyl 3-amino-4-chlorobenzoate (0.300 g, 1.62 mmol) in tetrahydrofuran (20 mL) was added a solution of lithium hydroxide (0.340 g, 8.10 mmol) in water (5 mL). The reaction mixture was stirred at room temperature for 12 hours (the reaction progress was monitored by silica gel thin layer chromatography with ethyl acetate-hexane as the unfolding agent, 1:1, v/v). After completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting lithium salt was acidified with 1% (w/v) citric acid solution at 0 °C and extracted with ethyl acetate (2 × 20 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-amino-4-chlorobenzoic acid as a white solid (yield 0.200 g, 72.01%).

Purification Methods

Crystallise the acid from water. [Beilstein 14 IV 1115.]

References

[1] Patent: US2012/184548, 2012, A1. Location in patent: Page/Page column 43

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