Chemical Fact Sheet

Chemical Abstract Number (CAS #) 106478
CASRN 106-47-8
Benzenamine, 4-chloro-
Analytical Method EPA Method 8270
Molecular FormulaC6H6ClN

Link to the National Library of Medicine's Hazardous Substances
Database for more details on this compound.

Use DYE INT, PHARMACEUTICALS, AGRICULTURAL CHEMICALS CHEM INT FOR DYES, EG, VAT RED 32 CHEM INT FOR AZOIC COUPLING AGENTS 5 & 10 CHEM INT FOR UREA HERBICIDES, EG, MONURON CHEM INT FOR PIGMENTS, EG, PIGMENT GREEN 10 Reacts with anhydrous hydrogen chloride and phosgene at 70-75 deg C in dioxane to produce p-chlorophenyl isocyanate, an intermediate used for the production of urea herbicides.
Boiling Point 232 DEG C @ 760 MM HG
Melting Point 72.5 DEG C
Molecular Weight 127.58
Density 1.169 @ 77 DEG C/4 DEG C
Sensitivity Data Irritating to the eyes.
Environmental Impact p-Chloroaniline may be released to the environment during its production or use in the manufacture of dye intermediates, agricultural chemicals and pharmaceuticals. If released on soil, it will rapidly combine chemically with soil components and partially be mineralized by chemical and biological action. A few percent of the p-chloroaniline will volatilize from the soil. If released into water p-chloroaniline will be primarily lost due to volatilization (half-life 6.4 hr), photooxidation in surface layers (half-life 0.4 hr), and rapid chemical reactions with humic materials and clay in the water column and sediment. Degradation in air will primarily be due to reaction with hydroxyl radicals (half-life 4.6 hr), although direct photolysis is also possible. Human exposure will primarily be in the workplace from inhalation or dermal contact.
Environmental Fate The average concn of chemicals, 4-chloroaniline, hexachlorobenzene, & pentachloronitrobenzene, dosed in small experimental ponds in Southern Germany during the application period (4-6 wk) was about 50 ug/l. Residues were determined in water, sediment, & flora & fauna species up to 166 wk later. Decrease of all chemicals in water phase follows exponential functions & can be correlated to some extent with the physicochemical properties such as volatility & vapor pressure. The residual behavior of the model compounds followed a similar pattern resulting in high initial concentrations in biota & a slow buildup & subsequent decline of concentrations in sediment. Radioactivity could be found in some fauna species & sediment 3 yr after application. Anisols & azo compounds were found to be conversion products of pentachloronitrobenzene & 4-chloroaniline. Three short-term lab test systems were used to determine volatilization rates, mineralization rates, & conversion rates of 14 (14)C-labeled chemicals one of which was p-chloroaniline. In order to compare data obtained with the environmental behavior of the respective chemicals, data from an outdoor experimental setup which had been shown to give residue data within the range limits of field conditions were used. Volatilization rates, mineralization rates, & conversion rates obtained in the lab were correlated to those found under outdoor conditions. The predicted values for total field residues were comparable to those found experimentally, with the exception of di(2-ethylhexyl)phthalate & p-chloroaniline. (14)C labeled 4-chloroaniline was applied to soil in lysimeter, corresponding to 1.25 ppm to a depth of 10 cm, & barley was sown. After 20 wk, a total of 32.8% of the radiocarbon applied was recovered, in soil 32.4%, in plants 0.3% & in leaching water 0.1%. Radioactivity in soil consisted of 30.8% unextractable residues & 1.6% sol conversion products; that in plants consisted of 0.24% unextractable residues & 0.03% sol metabolites (% of applied (14)C). In the 2nd & 3rd yr after the application potatoes & carrots, respectively, were grown; total recoveries were 32.0% & 31.2% respectively. The soluble radioactive fractions in soil & plants of the first 2 yr contained 4-chloroformanilide, 4-chloroacetanilide, 4-chloronitrobenzene, 4-chloronitrosobenzene, 4,4'-dichloroazoxybenzene, and 4,4'-dichloroazobenzene. The radioactive substances unextractable in soil and those in leaching water were partially hydrolyzable and gave 4-chloroaniline. TERRESTRIAL FATE: If released on soil, p-chloroaniline will bind tightly to soil although in the first few hours after a spill, a small amount will volatilize. The p-chloroaniline will undergo both biological and chemical transformation. Mineralization occurs most rapidly in the early weeks of incubation with as much as 7.5% degradation to CO2 occurring in 6 weeks and 17% occuring in 16 weeks. Most (70-90%) of the p-chloroaniline is transformed into inextractable residues and there is no significant leaching out either vertically or horizontally into surrounding layers of soil. A three year field test in which (14)C labeled p-chloroaniline was applied to 60X60X60 cm box cultivated with barley and later with potatoes and carrots under outdoor conditions resulted in approximately 30% of the applied radioactivity being retained at the application site in the upper layer of soil after the first year and 67% being lost to the atmosphere . Uptake by plants, migration into deeper soil layers or into leaching water was low . From previous experiments, it is known that the bulk of the atmospheric loss is not volatilized 4-chloroaniline or conversion products, but rather CO2 resulting from mineralization . The situation after the second and third year did not alter appreciably . No free unchanged 4-chloroaniline could be detected in either soil or plants . Conversion products isolated under these environmental conditions included 4-chloroformanilide, 4-chloroacetanilide, 4-chloronitrobenzene, 4-chloronitrosobenzene, and the condensation products 4,4'-dichloroazoxybenzene and 4,4'-dichloroazobenzene . It is hypothecized that phenolic and hydroxylamine metabolites were not identified although they were found in laboratory experiments because of their chemical instability . In summary, it is clear that free 4-chloroaniline is not presistent in soil; it is subject to various acylation and oxidation reactions and finally to total biodegradation and incorporation into soil and plant constituents(1,SRC). AQUATIC FATE: If released into water, p-chloroaniline will volatilize (half-life 6.4 hrs in a typical river), photooxidize in surface layers (half-life 0.4 hr), biodegrade (half-life several days in well acclimated water), and chemically bind to clays and humus in sediment and particulate matter in the water column. When (14)C labeled p-chloroaniline was added to an experimental pond, the (14)C label disappeared from the water phase in two phases with half-lives of about 3 and 11 days, respectively . It was assumed that the initial loss results from volatilization. After a day, a thin brown film of decomposition products was formed. The reduced loss rate after the first few days is probably a result of lower volatility of the decomposition products . In estuarine water, photolysis was also an important process, but no biodegradation occurred in 3 days . The half-life estimated by sampling at points along the Rhine River in the Netherlands is 0.3 to 3 days . ATMOSPHERIC FATE: If released into air, p-chloroaniline will degrade by reacting with photochemically produced hydroxyl radicals (half-life 4.6 hr) and possibly also by photolysis in the vapor phase or while adsorbed on airborne particulate matter. The rates for vapor phase photolysis are not available. A highly soluble chemical, p-chloroaniline will probably be scavenged by rain.
Drinking Water Impact DRINKING WATER: Germany (treated Rhine water source) 7 parts per trillion, annual average . The Netherlands; maximum from bank-filtered Rhine water 1 ppb, including m-isomer . SURFACE WATER: Not detected in Lakes Ontario (1 location), Erie (2 locations), Michigan (5 locations), and Superior (1 location). Rhine River (Germany) - 80 ppt, yearly average . Rhine River and two tributaries (The Netherlands) 130-220 ppt, average; 240-740 ppt maximum with 96-100% frequency of detection . Meuse River (The Netherlands) 20-30 ppt, average, 80-120 ppt maximum, 44-50% frequency of detection . While detected in Rhine Delta water, not found in surface waters from agricultural areas in the Netherlands .

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