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552224

Sigma-Aldrich

2-Amino-5-chlorophenol

97%

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Linear Formula:
H2NC6H3(Cl)OH
CAS Number:
28443-50-7
Molecular Weight:
143.57
EC Number:
249-020-3
MDL number:
MFCD02093863
PubChem Substance ID:
24879253
NACRES:
NA.22

Assay

97%

form

solid

mp

145-153 °C (lit.)

SMILES string

Nc1ccc(Cl)cc1O

InChI

1S/C6H6ClNO/c7-4-1-2-5(8)6(9)3-4/h1-3,9H,8H2

InChI key

FZCQMIRJCGWWCL-UHFFFAOYSA-N

General description

2-Amino-5-chlorophenol can be synthesized from 2-chloro-5-nitrophenol via reduction. It can also be obtained from 1-chloro-4-nitrobenzene by using a bacterial strain LW1. 2-Amino-5-chlorophenol participates in the condensation reaction with acetylferrocene to afford ferrocenyl Schiff bases bearing a phenol group.

Application

2-Amino-5-chlorophenol may be used to synthesize 2-amino-5-chloromuconic semialdehyde and benzoxazole derivatives.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Synthesis, characterization, and antimicrobial activity of cobalt (II), nickel (II), copper (II) and zinc (II) complexes with ferrocenyl Schiff bases containing a phenol moiety.
Abd-Elzaher MM.
Applied Organometallic Chemistry, 18(4), 149-155 (2004)
Anacardic acid derived salicylates are inhibitors or activators of lipoxygenases.
Wisastra R, et al.
Bioorganic & Medicinal Chemistry, 20(12), 5027-5032 (2012)
Synthesis and Crystal Structure of 1-Chloro-2-methyl-4-nitrobenzene.
Saeed A and Simpson J.
Crystals, 2(1), 137-143 (2012)
Jian-Feng Wu et al.
Archives of microbiology, 183(1), 1-8 (2004-12-08)
Comamonas strain CNB-1 was isolated from a biological reactor treating wastewater from a p-chloronitrobenzene production factory. Strain CNB-1 used p-chloronitrobenzene as sole source of carbon, nitrogen, and energy. A 2-aminophenol 1,6-dioxygenase was purified from cells of strain CNB-1. The purified
E Katsivela et al.
Applied and environmental microbiology, 65(4), 1405-1412 (1999-04-02)
Bacterial strain LW1, which belongs to the family Comamonadaceae, utilizes 1-chloro-4-nitrobenzene (1C4NB) as a sole source of carbon, nitrogen, and energy. Suspensions of 1C4NB-grown cells removed 1C4NB from culture fluids, and there was a concomitant release of ammonia and chloride.
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