2-Chloro-5-aminophenol Chemical Properties

Melting point:

160 °C

Boiling point:

185.5°C (rough estimate)

Density 

1.2028 (rough estimate)

refractive index 

1.5618 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO, Methanol

form 

Powder

pka

8.55±0.10(Predicted)

color 

Gray

Sensitive 

Light Sensitive

InChIKey

JSCNCRWPXOTDDZ-UHFFFAOYSA-N

CAS DataBase Reference

6358-06-1(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 5-amino-2-chloro- (6358-06-1)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

RTECS 

SJ5720000

HazardClass 

6.1

HS Code 

29089990

2-Chloro-5-aminophenol Usage And Synthesis

Chemical Properties

White powder

Uses

5-Amino-2-chlorophenol is used in the synthesis of antimalarial quinolones. Also used in the synthesis of potent anti-HIV agents based upon pyrimidinylphenylamine 1.

Synthesis

Step 1: 2-Chloro-5-nitrophenol (20.0 g, 115.2 mmol) was dissolved in a solvent mixture of ethanol (150 mL) and water (150 mL). To this solution, iron powder (32.2 g, 576.2 mmol) and ammonium chloride (32.1 g, 599.3 mmol) were added sequentially. The reaction mixture was heated to reflux and kept for 2 hours. After completion of the reaction, it was cooled to room temperature and filtered to remove insoluble material. The filtrate was concentrated to dryness under reduced pressure. The residue was purified by fast column chromatography (eluent: hexane/ethyl acetate = 9:1) to afford 5-amino-2-chlorophenol (15.85 g, 96% yield) as a white solid.

References

[1] Patent: US2003/100580, 2003, A1
[2] Patent: US2010/160388, 2010, A1. Location in patent: Page/Page column 58
[3] Patent: US2010/160389, 2010, A1. Location in patent: Page/Page column 49
[4] Patent: US2011/28502, 2011, A1. Location in patent: Page/Page column 44-45
[5] Patent: US2011/71143, 2011, A1. Location in patent: Page/Page column 36

2-Chloro-5-aminophenol(6358-06-1)Related Product Information

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