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158631

Sigma-Aldrich

4′-Chloroacetanilide

97%

Synonym(s):

N-(4-Chlorophenyl)acetamide, Acetic acid 4-chloroanilide, NSC 40563, NSC 444

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About This Item

Linear Formula:
CH3CONHC6H4Cl
CAS Number:
539-03-7
Molecular Weight:
169.61
Beilstein:
509638
EC Number:
208-707-8
MDL number:
MFCD00000612
UNSPSC Code:
12352100
PubChem Substance ID:
24849769
NACRES:
NA.22

Assay

97%

form

solid

mp

176-178 °C (lit.)

functional group

amide
chloro

SMILES string

CC(=O)Nc1ccc(Cl)cc1

InChI

1S/C8H8ClNO/c1-6(11)10-8-4-2-7(9)3-5-8/h2-5H,1H3,(H,10,11)

InChI key

GGUOCFNAWIODMF-UHFFFAOYSA-N

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General description

4′-Chloroacetanilide is the main impurity present in acetaminophen and has been quantitated by new high-performance liquid chromatography method using a mixed-mode reversed-phase/cation exchange stationary phase.

Application

<ul>
<li><strong>High-performance liquid chromatography (HPLC) method validation:</strong> 4 chloroacetanilide is used as an internal standard for isosorbide dinitrate in the assay of sustained-release tablets or capsules containing nitroglycerin, isosorbide dinitrate, or pentaerythritol tetranitrate by high-performance liquid chromatography (Gelber and Papas, 1983).</li>
</ul>

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000377739
0000366289
0000366290
MKCW7365
0000366289

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Acetamide ~99% (GC)

Sigma-Aldrich

A0500

Acetamide

4-Aminophenol United States Pharmacopeia (USP) Reference Standard

USP

1021204

4-Aminophenol

Benzamide 99%

Sigma-Aldrich

135828

Benzamide

L Koymans et al.
Xenobiotica; the fate of foreign compounds in biological systems, 23(6), 633-648 (1993-06-01)
1. The general mechanism of metabolic oxidation of substrates by cytochromes P450 (P450s) appears to consist of sequential one-electron oxidation steps rather than of a single concerted transfer of activated oxygen species from P450 to substrates. 2. In case of
Tamas A Godany et al.
Chimia, 65(4), 253-255 (2011-06-18)
Lithiation of N-(4-chlorophenyl)-pivalamide (NCP) and two additional substituted acetanilides: 4-fluoroacetanilide (4-F) and 4-chloroacetanilide (4-Cl) has been monitored by means of calorimetry, on-line ATR-IR and UV/vis spectroscopy and endoscopy. The combined on-line monitoring revealed the differences between the reaction paths of
Jody A Shoemaker et al.
Journal of AOAC International, 89(1), 201-209 (2006-03-04)
U.S. Environmental Protection Agency (EPA) Method 535 has been developed in order to provide a method for the analysis of "Alachlor ESA and other acetanilide degradation products," which are listed on EPA's 1998 Drinking Water Contaminant Candidate List. Method 535
Anthony F Pizon et al.
Clinical toxicology (Philadelphia, Pa.), 47(2), 132-136 (2008-07-09)
p-Chloroaniline is more potent at producing methemoglobin than aniline in animal models. This case highlights the clinical presentation of an inhalation exposure to p-chloroaniline and associated laboratory analysis. An in-vitro study evaluating the metabolism of p-chloroaniline in human hepatocytes was
Octavian Călinescu et al.
Journal of chromatographic science, 50(4), 335-342 (2012-03-13)
Determination of acetaminophen and its main impurities: 4-nitrophenol, 4'-chloroacetanilide, as well as 4-aminophenol and its degradation products, p-benzoquinone and hydroquinone has been developed and validated by a new high-performance liquid chromatography method. Chromatographic separation has been obtained on a Hypersil
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