Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6ClN |
| Molecular Weight | 127.572 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=C(Cl)C=C1
InChI
InChIKey=QSNSCYSYFYORTR-UHFFFAOYSA-N
InChI=1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
4-Chloroaniline (4-ClA) is a chlorinated aromatic amine that is formed as an intermediate during the microbial decomposition of phenylurea and phenylcarbamate. The formation of various oligomers by polymerization of 4-ClA with guaiacol in an aqueous solution containing oxidoreductases has been reported. 4-Chloroaniline is used as an intermediate in the production of
a number of products, including agricultural chemicals,
azo dyes and pigments, cosmetics, and pharmaceutical
products. Reactive metabolites of 4-Chloroaniline bind covalently to
haemoglobin and to proteins of liver and kidney. In
humans, haemoglobin adducts are detectable as early as
30 min after accidental exposure, with a maximum level
at 3 h. Repeated exposure to 4-Chloroaniline leads to cyanosis and
methaemoglobinaemia, followed by effects in blood,
liver, spleen, and kidneys, manifested as changes in
haematological parameters, splenomegaly, and moderate
to heavy haemosiderosis in spleen, liver, and kidney,
partially accompanied by extramedullary haematopoiesis. The marketing and use of products containing 4-Chloroaniline based
azo dyes were banned by the European
Union (EU) (EC, 2000).
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Estimation of bioconcentration factor of benzene derivatives]. | 2006 Dec |
|
| Transcriptional profiling reveals barcode-like toxicogenomic responses in the zebrafish embryo. | 2007 |
|
| Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides. | 2007 Apr 26 |
|
| Interaction between sodium hypochlorite and chlorhexidine gluconate. | 2007 Aug |
|
| Characterization of sulfonated azo dyes and aromatic amines by pyrolysis gas chromatography/mass spectrometry. | 2007 Aug |
|
| [A novel metabolism pathway for the biodegradation of chloroanilines]. | 2007 Feb |
|
| Urinary metabolites and health effects in workers exposed chronically to chloronitrobenzene. | 2007 Jan-Feb |
|
| Proton-transfer compounds of 8-hydroxy-7-iodoquinoline-5-sulfonic acid (ferron) with 4-chloroaniline and 4-bromoaniline. | 2007 Jul |
|
| Synthesis and antibacterial properties of new 8-nitrofluoroquinolone derivatives. | 2007 Jun 30 |
|
| Biodegradation of 4-chloroaniline by bacteria enriched from soil. | 2007 Mar |
|
| Continuous-flow microextration coupled with HPLC for the determination of 4-chloroaniline in Chlamydomonas reinhardtii. | 2007 May |
|
| Treatment of landfill leachate by electrochemical oxidation and anaerobic process. | 2007 May |
|
| Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms. | 2007 May 15 |
|
| Theoretical Raman and infrared spectra, and vibrational assignment for para-halogenoanilines: DFT study. | 2007 Nov |
|
| Exclusive production of chloroaniline from chloronitrobenzene over Au/TiO2 and Au/Al2O3. | 2008 |
|
| Mouse N-acetyltransferase type 2, the homologue of human N-acetyltransferase type 1. | 2008 Apr 1 |
|
| Interaction between chlorhexidine digluconate and EDTA. | 2008 Dec |
|
| Determination of para-chloroaniline and reactive oxygen species in chlorhexidine and chlorhexidine associated with calcium hydroxide. | 2008 Dec |
|
| A sweeping-micellar electrokinetic chromatography method for direct detection of some aromatic amines in water samples. | 2008 Feb |
|
| Natural attenuation, biostimulation, and bioaugmentation in 4-chloroaniline-contaminated soil. | 2008 Feb |
|
| Acridones circumvent P-glycoprotein-associated multidrug resistance (MDR) in cancer cells. | 2008 Jan 1 |
|
| A comparative study on the formation and characterization of aerobic 4-chloroaniline-degrading granules in SBR and SABR. | 2008 Jul |
|
| Analysis of primary aromatic amines using precolumn derivatization by HPLC fluorescence detection and online MS identification. | 2008 Mar |
|
| Layered material gamma-ZrP supported platinum catalyst for liquid-phase reaction: a highly active and selective catalyst for hydrogenation of the nitro group in para-chloronitrobenzene. | 2008 May 7 |
|
| Aqueous adsorption of aniline, phenol, and their substitutes by multi-walled carbon nanotubes. | 2008 Nov 1 |
|
| Determination of four aromatic amines in water samples using dispersive liquid-liquid microextraction combined with HPLC. | 2008 Sep |
|
| Potent CCR4 antagonists: synthesis, evaluation, and docking study of 2,4-diaminoquinazolines. | 2008 Sep 1 |
|
| Restoration of endodontically treated teeth review and treatment recommendations. | 2009 |
|
| Toxicology laboratory analysis and human exposure to p-chloroaniline. | 2009 Feb |
|
| Determination of aromatic amines in water samples by capillary electrophoresis with amperometric detection. | 2009 Jan |
|
| The spectroscopic (FTIR, FT-IR gas phase and FT-Raman), first order hyperpolarizabilities, NMR analysis of 2,4-dichloroaniline by ab initio HF and density functional methods. | 2009 Jul |
|
| Oxidation of 4-chloroaniline studied by on-line electrochemistry electrospray ionization mass spectrometry. | 2009 Jul 1 |
|
| Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases). | 2009 Mar |
|
| Is the p-chloroaniline anion bound almost entirely by correlation? | 2009 Mar 28 |
|
| Monoarylamines in the general population--a cross-sectional population-based study including 1004 Bavarian subjects. | 2009 May |
|
| Continuous quinacrine treatment results in the formation of drug-resistant prions. | 2009 Nov |
|
| Using diazotization to characterize the effect of heat or sodium hypochlorite on 2.0% chlorhexidine. | 2009 Sep |
|
| Synthesis, growth, spectral, thermal, mechanical and optical properties of 4-chloro-4'dimethylamino-benzylidene aniline crystal: a third order nonlinear optical material. | 2009 Sep 15 |
|
| Competitive adsorption of naphthalene with 2,4-dichlorophenol and 4-chloroaniline on multiwalled carbon nanotubes. | 2010 Apr 15 |
|
| An in vitro spectroscopic analysis to determine whether para-chloroaniline is produced from mixing sodium hypochlorite and chlorhexidine. | 2010 Feb |
|
| Determination of 4-chloroaniline and its derivatives formed in the interaction of sodium hypochlorite and chlorhexidine by using gas chromatography. | 2010 Feb |
|
| Sun light degradation of 4-chloroaniline in waters and its effect on toxicity. A high performance liquid chromatography - Diode array - Tandem mass spectrometry study. | 2010 Feb |
|
| Removal of direct azo dyes and aromatic amines from aqueous solutions using two beta-cyclodextrin-based polymers. | 2010 Feb 15 |
|
| Off-resonance effects in two-dimensional exchange NMR at zero-field. | 2010 Feb-Apr |
|
| The role of hypoxia in 2-butoxyethanol-induced hemangiosarcoma. | 2010 Jan |
|
| Biodegradation of 2-chloroaniline, 3-chloroaniline, and 4-chloroaniline by a novel strain Delftia tsuruhatensis H1. | 2010 Jul 15 |
|
| Determination of aromatic amines in environmental water sample by hollow fiber-liquid phase microextraction and microemulsion electrokinetic chromatography. | 2010 Jun 25 |
|
| Dihydrogen phosphate mediated supramolecular frameworks in 2- and 4-chloroanilinium dihydrogen phosphate salts. | 2010 Mar |
|
| A new on-line solid phase extraction high performance liquid chromatography tandem mass spectrometry method to study the sun light photodegradation of mono-chloroanilines in river water. | 2010 May 14 |
|
| Investigating the mechanisms of aromatic amine-induced protein free radical formation by quantitative structure-activity relationships: implications for drug-induced agranulocytosis. | 2010 May 17 |
Sample Use Guides
The lowest-observed-adverse effect
levels (LOAELs; no-observed-effect levels, or
NOELs, are not derivable) for a significant increase in
methaemoglobin levels in rats and mice are, respectively,
5 and 7.5 mg/kg body weight per day for a 13-
week oral administration of PCA by gavage (5 days/
week) and 2 mg/kg body weight per day for rats
administered PCA by gavage (5 days/week) at 26, 52,
78, and 103 weeks` exposure. Fibrotic changes of the
spleen were observed in male rats, with a LOAEL of
2 mg/kg body weight per day, and hyperplasia of bone
marrow was observed in female rats, with a LOAEL of
6 mg/kg body weight per day (103-week gavage).
Route of Administration:
Oral
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EPA PESTICIDE CODE |
17203
Created by
admin on Fri Dec 15 18:54:05 UTC 2023 , Edited by admin on Fri Dec 15 18:54:05 UTC 2023
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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C004658
Created by
admin on Fri Dec 15 18:54:05 UTC 2023 , Edited by admin on Fri Dec 15 18:54:05 UTC 2023
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4-CHLOROANILINE
Created by
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20331
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Z553SGH315
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106-47-8
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1111908
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7812
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2047
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m3388
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203-401-0
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DTXSID9020295
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36941
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PARENT (METABOLITE)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
