ChemicalBook--->CAS DataBase List--->6358-06-1

6358-06-1

6358-06-1 Structure

6358-06-1 Structure
IdentificationMore
[Name]

2-Chloro-5-aminophenol
[CAS]

6358-06-1
[Synonyms]

2-CHLORO-5-AMINOPHENOL
5-AMINO-2-CHLOROPHENOL
3-amino-6-chlorophenol
5-amino-2-chloro-pheno
4-Chloro-3-hydroxyaniline
2-ch1oro-5-aminophenol
[Molecular Formula]

C6H6ClNO
[MDL Number]

MFCD01707858
[Molecular Weight]

143.57
[MOL File]

6358-06-1.mol
Chemical PropertiesBack Directory
[Melting point ]

160 °C
[Boiling point ]

185.5°C (rough estimate)
[density ]

1.2028 (rough estimate)
[refractive index ]

1.5618 (estimate)
[storage temp. ]

Keep in dark place,Inert atmosphere,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]

6358-06-1(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Safety Statements ]

24/25
[RTECS ]

SJ5720000
[HazardClass ]

6.1
[HS Code ]

29089990
Hazard InformationBack Directory
[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]

2-Chloro-5-nitrophenol

619-10-3

2-Chloro-5-aminophenol

6358-06-1

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
Spectrum DetailBack Directory
[Spectrum Detail]

2-Chloro-5-aminophenol(6358-06-1)1HNMR
Well-known Reagent Company Product InformationBack Directory
[TCI AMERICA]

5-Amino-2-chlorophenol,>98.0%(GC)(T)(6358-06-1)
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