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CAS NUMBER: 106-47-8
EC NUMBER: 203-401-0
MOLECULAR FORMULA: C6H6ClN
MOLECULAR WEIGHT: 127.57
4-chloroaniline is a chloroaniline in which the chloro atom is para to the aniline amino group.
4-chloroaniline is a chloroaniline and a member of monochlorobenzenes.
4-Chloroaniline is an organochlorine compound with the formula ClC6H4NH2.
4-chloroaniline is one of the three isomers of chloroaniline.
4-Chloroaniline is not prepared from aniline, which tends to overchlorinate.
4-chloroaniline is prepared by reduction of 4-nitrochlorobenzene, which in turn is prepared by nitration of chlorobenzene.
4-Chloroaniline is a white or pale yellow solid with a sweet odor.
4-chloroaniline is used to make dyes, other chemicals, insecticides and many other industrial products.
4-chloroaniline 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-chloroaniline 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.
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.
4-Chloroaniline has been released into the environment due to extensive use in chemical industries and intensive agriculture; hence, it becomes one of the hazardous pollutants in the priority pollutant list.
In this study, three gram-negative bacteria were enriched and isolated from agricultural soil as 4-chloroaniline-degrading bacteria.
4-chloroanilines were identified as Acinetobacter baumannii CA2, Pseudomonas putida CA16 and Klebsiella sp. CA17.
4-chloroanilines were able to utilize 4-chloroaniline as a sole carbon and nitrogen source without stimulation or cocultivation with aniline or another cosubstrate. The biodegradation in these bacteria was occurred via a modified ortho-cleavage pathway of which the activity of chlorocatechol 1, 2-dioxygenase was markedly induced.
4-chloroanilines grew well on 0.2-mM 4-chloroaniline exhibiting a 60–75% degradation efficiency and equimolar liberation of chloride.
The isolates were able to survive in the presence of 4-chloroaniline at higher concentrations (up to 1.2 mM).
4-chloroaniline 3-chloroaniline and aniline, but not 3, 4-dichloroaniline, were also growth substrates for these isolates.
The results of cosubstrate supplementation illustrated the suitable conditions of each isolate to improve growth rate and 4-chloroaniline biodegradation efficiency.
These results suggest that these isolates have a potential use for bioremediation of the site contaminated with 4-chloroaniline.
4-Chloroaniline is one of the chlorinated aromatic amines that have been extensively used in the industrial production of dyes, cosmetics, pharmaceutical products and herbicides.
4-chloroaniline has been registered in the high production volume chemical program of the Organization for Economic Co-operation and Development.
Not only distributed through the industrial production, 4-chloroaniline is also one of the primary intermediates predominantly generated by microbial transformation of phenylurea, acylanilide and phenylcarbamate herbicides.
As a consequence of 4-chloroanilines intensive applications, 4-chloroaniline has been ubiquitous and accumulated in the environment including industrial effluent, sludge as well as agricultural soil. Due to its toxicity and recalcitrant properties, it has been considered as one of the important environmental pollutants.
To dissimilate the toxic compound, bioremediation can be applied as one of the remediation technologies in which a decontamination process depends on the microbial biodegradability.
Therefore, 4-chloroaniline many efforts have been undertaken to isolate bacteria capable of biodegradation of chloroanilin.
Although some microorganisms have been reported to have biodegradability towards 4-chloroanilines, their limitation is that they are unable to grow on chloroanilines as sole sources of carbon and nitrogen.
4-chloroaniline-degrading Comamonas testosteroni strain I2gfp capable of utilizing 3-chloroaniline as a sole source of carbon and nitrogen was isolated.
Nonetheless, under certain growth conditions, a few microorganisms have been reported to be able to grow on 4-chloroaniline as a sole carbon and nitrogen source.
For instance, previous studies stated that the bacterial isolations were successful only after they were cocultivated or induced in the presence of aniline or another cosubstrate, e.g. glucose, for some periods of time
4-Chloroaniline, also known as p-chloroaniline, is an organochlorine compound used for the production of drugs, and dyestuffs in the chemical industry.
Ungraded products supplied by TCI America are generally suitable for common industrial uses or for research purposes but typically are not suitable for human consumption or therapeutic use.
The 2D chemical structure image of 4-chloroaniline is also called skeletal formula, which is the standard notation for organic molecules.
The carbon atoms in the chemical structure of 4-chloroaniline are implied to be located at the corner(s) and hydrogen atoms attached to carbon atoms are not indicated – each carbon atom is considered to be associated with enough hydrogen atoms to provide the carbon atom with four bonds.
The 3D chemical structure image of 4-chloroaniline is based on the ball-and-stick model which displays both the three-dimensional position of the atoms and the bonds between them. The radius of the spheres is therefore smaller than the rod lengths in order to provide a clearer view of the atoms and bonds throughout the chemical structure model of 4-CHLOROANILINE.
4-chloroaniline molecule contains a total of 14 bond(s).
There are 8 non-H bond(s), 6 multiple bond(s), 6 aromatic bond(s), 1 six-membered ring(s) and 1 primary amine(s) (aromatic).
4-chloroaniline molecule shown in the visualization screen can be rotated interactively by keep clicking and moving the mouse button.
The information of the atoms, bonds, connectivity and coordinates included in the chemical structure of 4-chloroaniline can easily be identified by this visualization.
By right-clicking the visualization screen, various other options are available including the visualization of van der Waals surface and exporting to a image file.
4-Chloroaniline is a colourless to slightly amber-coloured crystalline solid with a mild aromatic odour.
4-chloroaniline is Soluble in hot water and organic solvents.
4-Chloroaniline has a moderate vapour pressure and n-octanol/ water partition coefficient.
4-chloroaniline decomposes in the presence of light and air and at elevated temperatures.
4-Chloroaniline is an important building block used in the chemical industry for the production of drugs and dyestuffs.
Some benzodiazepine drugs use 4-chloroaniline in their manufacture.
4-Chloroaniline(is also called PCA) is used as an intermediate in the production of a number of products, including agricultural chemicals, azo dyes and pigments, cosmetics, and pharmaceutical products.
4-Chloroaniline is incompatible with oxidizing agents.
4-chloroaniline is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates.
Subject to exothermic decomposition during high-temperature distillation.
Incompatible with nitrous acid.
4-chloroaniline was applied to a soil at a depth of 10 cm.
4-Chloroaniline covalently bonds with humates in soils to form quinoidal structures followed by oxidation to yield a nitrogen-substituted quinoid ring.
USES:
4-Chloroaniline is used in the industrial production of pesticides, drugs, and dyestuffs.
4-chloroaniline is a precursor to the widely used antimicrobial and bacteriocide chlorhexidine and is used in the manufacture of pesticides, including pyraclostrobin, anilofos, monolinuron, and chlorphthalim.
4-Chloroaniline exhibits antimicrobial action against some bacteria and molds.
APPLICATION:
4-Chloroaniline can undergo:
-Allylation in the presence of ultrasonication to form N-allyl-4-chloroaniline, a precursor for bioactive compounds containing indole and dihydroindole nucleus.
-Povarov reaction with cyclopentadiene to form C-2 aliphatic substituted tetrahydroquinolines.
-Mannich reaction with aldehydes and cyclic ketones to form β-amino carbonyl compounds.
-Nitration to form 4-chloro-3-nitroaniline in the presence of guanidinium nitrate.
PROPERTIES:
-Quality Level: 200
-vapor pressure: 0.07 hPa ( 20 °C)
-assay: ≥99.0% (GC)
-form: solid
-autoignition temp.: 685 °C
-potency: 256 mg/kg LD50, oral (Rat), 360 mg/kg LD50, skin (Rabbit)
-pH: 6.9 (20 °C, 1 g/L in H2O)
-Boiling point: 232 °C/1013 hPa
-Melting point: 66-69 °C
-transition temp: flash point 132 °C
PHYSICAL AND CHEMICAL PROPERTIES:
-Boiling point: 232 °C (1013 hPa)
-Density: 1.17 g/cm3 (70 °C)
-Flash point: 120.0 °C DIN 51758
-Ignition temperature: 685 °C
-Melting Point: 66 - 69 °C
-pH value: 6.9 (1.00000 g/l, H₂O, 20.0 °C)
-Vapor pressure: 0.4 hPa (38.0 °C)
-Bulk density: 790 kg/m3
-Solubility: 2.2 g/l
SPECIFICATION:
-Color: Beige to Brown-Purple
-Melting Point: 68.0°C to 72.0°C
-Boiling Point: 232.0°C
-Flash Point: >188°C
-Assay Percent Range: 97.5% min. (GC)
-Linear Formula: ClC6H4NH2
-Beilstein: 12,607
CHEMICAL PROPERTIES:
-Melting point: 67-70 °C (lit.)
-Boiling point: 232 °C (lit.)
-density: 1,43 g/cm3
-vapor density: 4.4 (vs air)
-vapor pressure: 0.15 mm Hg ( 25 °C)
-refractive index: 1.5546
-Fp: 120°C
-storage temp.: Store below +30°C.
-solubility: 2.2g/l
-form: Crystalline Solid
-pka: 4.15(at 25℃)
-color: Beige to brown-purple
-Specific Gravity: 1.2417
-Odor: Sweetish
-PH: 6.9 (1g/l, H2O, 20℃)
-PH Range: 6.9 at 1.00000 g/l at 20 °C
-Water Solubility: 0.3 g/100 mL (20 ºC)
-Merck: 14,2118
-BRN: 471359
-Henry's Law Constant: 1.07 at 25 °C
TECHNICAL INFORMATION:
-Solubility: Soluble in water (within almost transparency), methanol (almost transparency), and DMSO.
-Storage: Store at room temperature
-Melting Point: >230° C (subl.)
-Boiling Point: 232° C at 760 mmHg (Predicted)
-Refractive Index: n20D 1.60 (Predicted)
STORAGE:
Store below +30°C.
SYNONYM:
p-Chloroaniline
4-Chlorobenzenamine
p-Chloraniline
Benzenamine, 4-chloro-
para-Chloroaniline
p-Chlorophenylamine
4-Chlorophenylamine
1-Amino-4-chlorobenzene
p-Aminochlorobenzene
4-Aminochlorobenzene
4-Amino-1-chlorobenzene
4-Chloro-1-aminobenzene
Aniline, p-chloro-
4-Chloro-phenylamine
4-Chloranilin
p-CA
4-Chlorobenzeneamine
Aniline, 4-chloro-
Benzeneamine, 4-chloro
4-chloro aniline
RCRA waste number P024
NCI-C02039
NSC 36941
UNII-Z553SGH315
CHEBI:20331
IUPAC NAME:
4-Chloroaniline
4-chloroaniline
4-Chloroaniline
4-chloroaniline
Benzenamine, 4-chloro
p-Chloranilin
TRADE NAME:
4-Chlorophenylamine
Aniline, p-chloro- (8CI)
Benzenamine, 4-chloro- (9CI)
p-Aminochlorbenzene
p-Aminochlorobenzene
p-Chloranilin
p-Chloroaniline
p-chloroaniline
p-Chlorophenylamine
para-Aminochlorobenzene
