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Sigma-Aldrich

4-Amino-2-chlorophenol

98%

Synonym(s):

3-Chloro-4-hydroxyaniline

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About This Item

Linear Formula:
H2NC6H3(Cl)OH
CAS Number:
3964-52-1
Molecular Weight:
143.57
MDL number:
MFCD00128891
UNSPSC Code:
12352100
PubChem Substance ID:
24867364
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

150-153 °C (lit.)

SMILES string

Nc1ccc(O)c(Cl)c1

InChI

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

InChI key

ZYZQSCWSPFLAFM-UHFFFAOYSA-N

General description

4-Amino-2-chlorophenol (4A2CP) is a chlorinated aniline. Nephrotoxic potential of 4-amino-2-chlorophenol and its comparison with 4-aminophenol, 4-amino-2-chlorophenol, 4-amino-3-chlorophenol and 4-amino-2,6-dichlorophenol using isolated renal cortical cells from male Fischer 344 rats has been investigated.

Application

4-Amino-2-chlorophenol may be used in the synthesis of the following compounds:
  • N-(3-chloro-4-hydroxyphenyl)-N′,N′-dimethylurea
  • 1,4-diketo-3-((4-[N-(3-chloro-4-hydroxyphenyl)amino]sulfonyl)phenyl)-6-phenylpyrrolo[3,4-c]pyrrole, a novel fluorescent pH-indicator
  • 4-(4-aminophenoxy)-N-(4-(4-aminophenoxy) benzylidene)-3-chloroaniline
  • 4-(4-amino-3-methylphenoxy)-N-(4-(4-amino-3-methylphenoxy)benzylidene)-3-chloroaniline
  • 4-(4-amino-2-methylphenoxy)-N-(4-(4-amino-2-methylphenoxy)benzylidene)-3-chloroaniline

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fluorescent materials for pH sensing and imaging based on novel 1,4-diketopyrrolo-[3,4-c] pyrrole dyes.
Aigner D, et al.
Journal of Material Chemistry C, 1(36), 5685-5693 (2013)
Gary O Rankin et al.
Chemico-biological interactions, 222, 126-132 (2014-12-03)
Chlorinated anilines are nephrotoxicants both in vivo and in vitro. The mechanism of chloroaniline nephrotoxicity may occur via more than one mechanism, but aminochlorophenol metabolites appear to contribute to the adverse in vivo effects. The purpose of this study was
S K Hong et al.
Toxicology, 110(1-3), 47-58 (1996-06-17)
Aminophenols and halogenated anilines induce nephrotoxicity and mild hepatotoxicity in rats. In this study, the in vivo and in vitro nephrotoxic potential of 4-amino-2-chlorophenol and 2-amino-4-chlorophenol, monochlorinated aminophenols and potential metabolites of 3-chloroaniline, was evaluated. Hepatotoxicity of both compounds was
C Tixier et al.
Environmental toxicology and chemistry, 20(7), 1381-1389 (2001-07-04)
The degradation products of diuron (photoproducts and metabolites), already described in the literature, were synthesized in order to carry out further investigations. Their ecotoxicity was determined using the standardized Microtox test, and most of the derivatives presented a nontarget toxicity
Synthesis and Characterization of Novel Processable and Flexible Polyimides Containing 3, 6-Di(4-carboxyphenyl) pyromellitic Dianhydride.
Khosa MK, et al.
Advances in Chemistry, 2014 (2014)
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