5-Amino-2-chlorobenzoic acid Chemical Properties

Melting point:

184-188 °C (lit.)

Boiling point:

250°C (rough estimate)

Density 

1.5

refractive index 

1.5570 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

479mg/l

pka

1.99±0.25(Predicted)

form 

powder to crystal

color 

White to Light yellow

BRN 

2090422

InChI

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

InChIKey

GVCFFVPEOLCYNN-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

89-54-3(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 5-amino-2-chloro- (89-54-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:5-Amino-2-chlorobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Amino-2-chlorobenzoic acid Usage And Synthesis

Chemical Properties

White solid

Uses

5-Amino-2-chlorobenzoic Acid is a reagent in the preparation of potent and selective benzothiazole hydrazone inhibitors of Bcl-XL.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 5-amino-2-chlorobenzoic acid from 2-chloro-5-nitrobenzoic acid: 75 g of 2-chloro-5-nitrobenzoic acid, 59 g of iron powder, 800 mL of ethanol, 150 mL of water, and 115 g of ammonium chloride were added to a reaction flask equipped with a stirrer. The mixture was heated to 78-80°C and the reaction was refluxed for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent was petroleum ether/ethyl acetate=1:3) during the reaction. Upon completion of the reaction, the reaction mixture was filtered while hot and the solids were washed with 150 mL of hot ethanol. The filtrate was dried at 60°C to obtain the crude product. Subsequently, the crude product was dissolved in 400 mL of ethyl acetate and heated to reflux pulping for 2 hours. The mixture was cooled to 0~5°C in a salt bath and then naturally reduced to room temperature and crystallized for more than 30 minutes. The crystals were separated by centrifugation and washed with 50 mL of ethyl acetate. Finally, it was dried under reduced pressure at 50°C to give 60.7 g of yellow solid 5-amino-2-chlorobenzoic acid with 99.1% purity and 95.1% yield.

References

[1] Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 3, p. 183 - 186
[2] Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 9, p. 3462 - 3467
[3] Patent: CN106748721, 2017, A. Location in patent: Paragraph 0029; 0030
[4] Angewandte Chemie - International Edition, 1999, vol. 38, # 18, p. 2777 - 2779
[5] Justus Liebigs Annalen der Chemie, 1868, vol. 147, p. 258

5-Amino-2-chlorobenzoic acid(89-54-3)Related Product Information

• POLYURETHANE
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• Glycine
• Ethyl 2-(Chlorosulfonyl)acetate
• Urethane
• ALTRENOGEST
• 4-Chlorobenzoic acid
• 4-Aminobenzoic acid
• Epichlorohydrin
• 2-Chlorobenzoic acid
• Difluorochloromethane
• Methyl 2-chloro-5-nitrobenzoate
• 2,6-DICHLORO-3-NITROBENZOIC ACID
• 2-Chloro-3,5-dinitrobenzoic acid
• 2,4-DICHLORO-3,5-DINITROBENZOIC ACID
• Chloroacetic acid
• Anthranilic acid
• Ethyl 2-chloro-5-nitrobenzoate