4-Amino-2-chlorobenzoic acid Chemical Properties

Melting point:

211 °C (dec.) (lit.)

Boiling point:

250°C (rough estimate)

Density 

1.3246 (rough estimate)

refractive index 

1.5560 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Powder

pka

3.81±0.25(Predicted)

color 

Beige to light brown

BRN 

2803668

InChI

InChI=1S/C7H6ClNO2/c8-6-3-4(9)1-2-5(6)7(10)11/h1-3H,9H2,(H,10,11)

InChIKey

MBDUKNCPOPMRJQ-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(N)C=C1Cl

CAS DataBase Reference

2457-76-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-amino-2-chloro-(2457-76-3)

EPA Substance Registry System

Benzoic acid, 4-amino-2-chloro- (2457-76-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

DG1575000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29224995

MSDS

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4-Amino-2-chlorobenzoic acid Usage And Synthesis

Chemical Properties

beige to light brown powder

Uses

4-Amino-2-chlorobenzoic acid is the principal metabolite of 2-Chloroprocaine, a compound that is widely used for epidural analgesia in obstetrics.

Definition

ChEBI: 4-Aminobenzoic acid in which one of the hydrogens ortho- to the carboxylic acid group is substituted by chlorine.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of 4-amino-2-chlorobenzoic acid from 2-chloro-4-nitrobenzoic acid was as follows: firstly, NaBH4 (1 mmol) was added as a reducing agent to methanol at room temperature and the reaction was carried out for 2 h. Ag (+1) was reduced to Ag (0). Subsequently, the Ag/MMT catalyst was obtained by filtration separation. In a standard reaction procedure, 2-chloro-4-nitrobenzoic acid (0.1 mmol), KOH (0.15 mmol), isopropanol (3 mL) and 1.01 wt% of Ag/MMT catalyst (50 mg) were mixed and the reaction was stirred at room temperature until completion (the reaction progress was monitored by GC). Upon completion of the reaction, the catalyst was removed by filtration. The product was extracted with ethyl acetate and washed repeatedly (3-4 times) with water to remove residual KOH. finally, the solvent in the extract was evaporated to dryness under vacuum to afford the target product 4-amino-2-chlorobenzoic acid.

References

[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 27, p. 6730 - 6739
[2] Journal of the Iranian Chemical Society, 2018, vol. 15, # 2, p. 281 - 291
[3] Patent: US2014/18368, 2014, A1. Location in patent: Paragraph 0162; 0187
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 4154
[5] Chemische Berichte, 1891, vol. 24, p. 706

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