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
| Molecular Formula | C6H6ClN |
| Molecular Weight | 127.572 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Biodegradation of 2-chloroaniline, 3-chloroaniline, and 4-chloroaniline by a novel strain Delftia tsuruhatensis H1. | 2010-07-15 |
|
| Determination of aromatic amines in environmental water sample by hollow fiber-liquid phase microextraction and microemulsion electrokinetic chromatography. | 2010-06-25 |
|
| Investigating the mechanisms of aromatic amine-induced protein free radical formation by quantitative structure-activity relationships: implications for drug-induced agranulocytosis. | 2010-05-17 |
|
| 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. | 2010-05-14 |
|
| Competitive adsorption of naphthalene with 2,4-dichlorophenol and 4-chloroaniline on multiwalled carbon nanotubes. | 2010-04-15 |
|
| Dihydrogen phosphate mediated supramolecular frameworks in 2- and 4-chloroanilinium dihydrogen phosphate salts. | 2010-03 |
|
| Removal of direct azo dyes and aromatic amines from aqueous solutions using two beta-cyclodextrin-based polymers. | 2010-02-15 |
|
| An in vitro spectroscopic analysis to determine whether para-chloroaniline is produced from mixing sodium hypochlorite and chlorhexidine. | 2010-02 |
|
| Determination of 4-chloroaniline and its derivatives formed in the interaction of sodium hypochlorite and chlorhexidine by using gas chromatography. | 2010-02 |
|
| Sun light degradation of 4-chloroaniline in waters and its effect on toxicity. A high performance liquid chromatography - Diode array - Tandem mass spectrometry study. | 2010-02 |
|
| The role of hypoxia in 2-butoxyethanol-induced hemangiosarcoma. | 2010-01 |
|
| Continuous quinacrine treatment results in the formation of drug-resistant prions. | 2009-11 |
|
| Synthesis, growth, spectral, thermal, mechanical and optical properties of 4-chloro-4'dimethylamino-benzylidene aniline crystal: a third order nonlinear optical material. | 2009-09-15 |
|
| Using diazotization to characterize the effect of heat or sodium hypochlorite on 2.0% chlorhexidine. | 2009-09 |
|
| Off-resonance effects in two-dimensional exchange NMR at zero-field. | 2009-08-25 |
|
| Oxidation of 4-chloroaniline studied by on-line electrochemistry electrospray ionization mass spectrometry. | 2009-07-01 |
|
| 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. | 2009-07 |
|
| Monoarylamines in the general population--a cross-sectional population-based study including 1004 Bavarian subjects. | 2009-05 |
|
| Is the p-chloroaniline anion bound almost entirely by correlation? | 2009-03-28 |
|
| Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases). | 2009-03 |
|
| Toxicology laboratory analysis and human exposure to p-chloroaniline. | 2009-02 |
|
| Determination of aromatic amines in water samples by capillary electrophoresis with amperometric detection. | 2009-01 |
|
| Restoration of endodontically treated teeth review and treatment recommendations. | 2009 |
|
| Interaction between chlorhexidine digluconate and EDTA. | 2008-12 |
|
| Determination of para-chloroaniline and reactive oxygen species in chlorhexidine and chlorhexidine associated with calcium hydroxide. | 2008-12 |
|
| Aqueous adsorption of aniline, phenol, and their substitutes by multi-walled carbon nanotubes. | 2008-11-01 |
|
| Potent CCR4 antagonists: synthesis, evaluation, and docking study of 2,4-diaminoquinazolines. | 2008-09-01 |
|
| Determination of four aromatic amines in water samples using dispersive liquid-liquid microextraction combined with HPLC. | 2008-09 |
|
| A comparative study on the formation and characterization of aerobic 4-chloroaniline-degrading granules in SBR and SABR. | 2008-07 |
|
| 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. | 2008-05-07 |
|
| Mouse N-acetyltransferase type 2, the homologue of human N-acetyltransferase type 1. | 2008-04-01 |
|
| Analysis of primary aromatic amines using precolumn derivatization by HPLC fluorescence detection and online MS identification. | 2008-03 |
|
| A sweeping-micellar electrokinetic chromatography method for direct detection of some aromatic amines in water samples. | 2008-02 |
|
| Natural attenuation, biostimulation, and bioaugmentation in 4-chloroaniline-contaminated soil. | 2008-02 |
|
| Acridones circumvent P-glycoprotein-associated multidrug resistance (MDR) in cancer cells. | 2008-01-01 |
|
| Exclusive production of chloroaniline from chloronitrobenzene over Au/TiO2 and Au/Al2O3. | 2008 |
|
| Theoretical Raman and infrared spectra, and vibrational assignment for para-halogenoanilines: DFT study. | 2007-11 |
|
| Interaction between sodium hypochlorite and chlorhexidine gluconate. | 2007-08 |
|
| Characterization of sulfonated azo dyes and aromatic amines by pyrolysis gas chromatography/mass spectrometry. | 2007-08 |
|
| Proton-transfer compounds of 8-hydroxy-7-iodoquinoline-5-sulfonic acid (ferron) with 4-chloroaniline and 4-bromoaniline. | 2007-07 |
|
| Synthesis and antibacterial properties of new 8-nitrofluoroquinolone derivatives. | 2007-06-30 |
|
| Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms. | 2007-05-15 |
|
| Continuous-flow microextration coupled with HPLC for the determination of 4-chloroaniline in Chlamydomonas reinhardtii. | 2007-05 |
|
| Treatment of landfill leachate by electrochemical oxidation and anaerobic process. | 2007-05 |
|
| Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides. | 2007-04-26 |
|
| Urinary metabolites and health effects in workers exposed chronically to chloronitrobenzene. | 2007-04-19 |
|
| Biodegradation of 4-chloroaniline by bacteria enriched from soil. | 2007-03 |
|
| [A novel metabolism pathway for the biodegradation of chloroanilines]. | 2007-02 |
|
| Transcriptional profiling reveals barcode-like toxicogenomic responses in the zebrafish embryo. | 2007 |
|
| [Estimation of bioconcentration factor of benzene derivatives]. | 2006-12 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:25:03 GMT 2025
by
admin
on
Mon Mar 31 19:25:03 GMT 2025
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| Record UNII |
Z553SGH315
|
| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
17203
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300000053057
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C004658
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4-CHLOROANILINE
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20331
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Z553SGH315
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m3388
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203-401-0
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DTXSID9020295
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PARENT -> METABOLITE |
URINE
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PARENT -> IMPURITY |
TITRATION
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
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