2,4-Dichloranilin

log Kow= 2.91

2.78

1.567 at 68 °F (NTP, 1992) - Denser than water; will sink

1.567 @ 20 °C

1.57 g/cm³

less than 1 mg/mL at 73 °F (NTP, 1992)

Slightly soluble in water, alcohol, and ether.

Solubility in water: none

473 °F at 760 mmHg (NTP, 1992)

245 °C AT 760 mm Hg

245 °C

When heated to decomposition it emits toxic vapors of nitrogen oxides and /hydrogen chloride/.

370 °C. Decomposes on burning. This produces toxic fumes including nitrogen oxides and hydrogen chloride (see ICSC 0163).

145 to 147 °F (NTP, 1992)

63-64 °C

63-64 °C

Danger

H301 (96.4%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 55 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Chemical: Benzenamine, 2,4-dichloro-

Benzenamine, 2,4-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2,4-dichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 03-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1436

2,4-Dichloroaniline: Does not have an individual approval but may be used under an appropriate group standard

Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Heating will cause rise in pressure with risk of bursting.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,4-Dichlorobenzeneamine is included on this list.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 2,4-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

If material on fire or involved in fire: Use dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. use water in flooding quantities as fog. /Dichloroaniline/

Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Dichloroaniline/

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: chemical protection suit including self-contained breathing apparatus. Remove all ignition sources. Do NOT wash away into sewer. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

... ANILINE SHOULD BE REACTED IN CLOSED VESSELS AS FAR AS POSSIBLE. IN FACTORIES VENTILATION SHOULD BE SUFFICIENT TO KEEP ATMOSPHERIC ANILINE CONTENT WELL BELOW PERMITTED LEVEL. /ANILINE/

Eating and smoking should not be allowed in areas where liquid aniline is handled, processed, or stored. /Aniline/

Clothing which becomes soaked with aniline should be promptly removed. /Aniline/

For more Preventive Measures (Complete) data for 2,4-DICHLOROANILINE (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 525(2), indicates that 2,4-dichloroaniline is expected to have low mobility in soil(SRC). Volatilization of 2,4-dichloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2,4-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(4). Adsorption to soil is expected to attenuate volatilization(SRC). In shake-flask screening tests using soil microbes adapted to isopropyl N-phenylcarbamate, ring degradation of 86-100% was observed for 2,4-dichloroaniline over incubation periods of 8-22 days(5).

AQUATIC FATE: Based on a classification scheme(1),a Koc value of 525(2), indicates that 2,4-dichloroaniline is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 30 and 219 days, respectively(SRC), using an estimation method(3). However, this model underestimates the volatilization half-life of 2,4-dichloroaniline since it does not take into account the effects of adsorption. The Koc of 525(2) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half-life = 842 days in a model pond) and one in which adsorption was ignored (half-life = 317 days in a model pond)(5). A BCF of 94.7(6), suggests bioconcentration in aquatic organisms is moderate. The photochemical degradation process of 2,4-dichloroaniline in aquatic environments was linear according to the first-order decay rate(7). Photolysis rate constants of 0.071/hr and 0.033/hr in water were determined for summer and winter conditions, respectively, corresponding to respective half-lives of 10 and 21 hrs(8). No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semi-volatile organic compounds in the atmosphere(1), 2,4-dichloroaniline, which has an estimated vapor pressure of 1.5X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dichloroaniline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 42 hours(SRC) from its estimated rate constant of 9.2X10-12 cu cm/molecule sec(3). 2,4-Dichloroaniline absorbs light in the environmental spectrum (>290 nm) and may undergo direct photolysis(4,5); half-lives in water ranged from 10-21 hours(5).

Blue lips, fingernails and skin. Dizziness. Headache. Nausea. Shortness of breath. Confusion. Convulsions. Unconsciousness.

MAY BE ABSORBED! Redness. Further see Inhalation.

Redness. Pain.

Abdominal pain. Further see Inhalation.

2,4-Dichloroaniline was found to occur only once in over 4000 samples of waste waters from 46 industrial categories(1). It was detected in the wastewater effluent generated from the organic chemicals industry, concentration not specified(1). 2,4-Dichloroanilne was detected in sewage sludge from Brandenburg, Germany during the summer at 0.8 mg/kg (median) and 2 mg/kg (max) while during winter it was detected at 0.2 mg/kg (median) and 0.6 mg/kg (max) in sewer sludge dry matter(2).

The Koc of 2,4-dichloroaniline is 525(1). According to a classification scheme(2), this Koc value suggests that 2,4-dichloroaniline will have low mobility in soil. A Koc of 3930 was measured at pH 6.5 using a colloidal-sized fraction of dissolved organic carbon isolated from groundwater monitoring wells(3). In soil column leaching studies simulating waste leaching from landfill sites, 2,4-dichloroaniline exhibited moderate leaching when leached in combination with leachate from domestic landfill sites(4). Aromatic amines (such as various chloro- and dichloroaniline isomers) have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution. The initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures in humic material followed by oxidation of the product to give an amino-substituted quinone(5).

2,4-Dichloroaniline's production and use as an intermediate in the production of dyestuffs, pesticides or pharmaceuticals(1,2) may result in its release to the environment through various waste streams(SRC). Aromatic amines (such as 2,4-dichloroaniline) are introduced into the environment directly as industrial effluents and indirectly as transformation products(1). Dichloroanilines arise from corresponding nitrodichloroanilines when the latter are metabolized by fungi(3).

AEROBIC: Biodegradation of 2,4-dichloroaniline was not observed in freshwater samples if no sunlight was present. Photolysis of 2,4-dichloroaniline increased bacterial numbers presumably due to the utilization of the degradation products formed(1). Incubation of 2,4-dichloroaniline in covered beakers containing a sandy loam soil for 14 days yielded the azo compound 2,2',4,4'-tetrachloroazobenzene(2). No azo compounds were detected in control incubations using sterilized soil. Products other than azo compounds were not isolated or analyzed for(2). In shake-flask screening tests using soil microbes adapted to isopropyl N-phenylcarbamate, ring degradation of 86-100% was observed for 2,4-dichloroaniline over incubation periods of 8-22 days(3). No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia(4).

ANAEROBIC: In unacclimated sediment slurries spiked with 10 mg/l of 2,4-dichloroaniline, dechlorination to the monochlorophenol intermediates began after a lag period of 4 weeks and was complete within the following 10 days. In acclimated sediments, dechlorination to monochlorophenol intermediates began immediately and was complete in 9 days. 2,4-Dichloroaniline was reductively dechlorinated in dichlorophenol acclimated sediments without lag(1).

A BCF of 94.7 was experimentally determined for 2,4-dichloroaniline under static conditions in a closed basin with 60 male zebra fish and 5000 ml of carbon filtered tap water(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Henry's Law constant for 2,4-dichloroaniline is estimated as 1.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4-dichloroaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 711 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 219 days(SRC). However, the volatilization half-life does not take into account the effects of adsorption. A Koc value of 525(3) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 842 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 317 days in a model pond 2 m deep(4). 2,4-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,4-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(5).

TWENTY-ONE HALO-SUBSTITUTED ANILINES WERE COMPARED WITH ANILINE FOR THEIR ABILITY TO STIMULATE METHEMOGLOBIN FORMATION IN CATS. HALO SUBSTITUTIONS IN THE 4-POSITION INCREASED THE ACTIVITY OF ANILINE, WHILE SUBSTITUTIONS IN THE 2 AND 3 POSITIONS DID NOT CHANGE OR REDUCE THE ACTIVITY. POLYHALO SUBSTITUENTS (SUCH AS 2,6-DICHLOROANILINE) REDUCED THE ACTIVITY COMPARED TO ANILINE. /DICHLOROANILINES/

IN GUELPH LOAM, 2,4-DICHLOROANILINE, AT CONCN OF 5-100 UG/G SOIL, WAS INHIBITORY AGAINST THE OXIDN OF THE NITROGEN OF AMMONIA TO NITRITE NITROGEN BY NITROSOMONAS, BUT NOT NITRITE NITROGEN TO NITRATE. THE DICHLOROANILINES SHOWED INCREASED TOXICITY AGAINST NITROSOMONAS.

Ten substances were tested to compare two methods that can be used in chronic toxicity studies with the cladoceran Daphnia magna. In semistatic experiments with cohorts (life-table studies) survival appeared to be a dominant factor in exponential population growth. Specific inhibition of reproduction as a result of toxic stress was observed in tests with 2,4-dichloroaniline.

Dichloroaniline produces methemoglobinemia in rats & mice. /Dichloroaniline/

Like other chloroanilines, the primary toxic effect of 2,4-, 2,5-, and 3,4-dichloroaniline is methemoglobin formation, which is attributed to the intermediate formation of hydroxylated metabolites. Acute intoxication is indicated by the symptoms of methemoglobinemia (cyanosis, fatigue, dyspnoea, muscle weakness). Judging by doses which had an effect in animal experiments, dichloroanilines showed moderate acute toxicity. After occlusive application to experimental animals, 2,4-dichloroaniline was moderately irritant on skin. 3,4-dichloroaniline was not irritant on rabbit skin, and the results for irritancy in the eye varied from not irritant to irritant. The 2,5-isomer was not irritant on rabbit skin, but caused irritant effects in the eye; the effects were severe and not completely reversible. The hyperkeratogenous and acnegenic effects documented in the literature were attributed to 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene, impurities formerly present in industrial 3,4-dichloroaniline. 3,4-dichloroaniline had no photoallergic effect on the mouse. The maximization test on the guinea pig revealed that 3,4- and 2,5-dichloroaniline had skin sensitizing potential. There are no data on the sensitizing effect of the 2,4-isomer. Like after acute application, hematological changes become evident after repeated application of dichloroanilines. An increase in both haemoglobin break-down and hematopoiesis was observed in the rat after subacute oral administration of 2,5-dichloroaniline at doses of 150 mg/kg body weight and above. The NOEL was 30 mg/kg body weight per day. After repeated administration of 3,4-dichloroaniline by inhalation (6 h/d, 5 d/w over 2 weeks), there was evidence of slight methemoglobin formation at an exposure concentration of 10 mg/cu m and above, histopathological changes in the spleen (hemosiderin deposits) at 45 mg/cu m and above and extramedullary hematopoiesis at 200 mg/cu m. Most of the mutagenicity tests carried out did not indicate any genotoxic effects of dichloroanilines. None of the isomers considered here was mutagenic in the numerous Ames tests, either with or without metabolic activation, or when Norharman was added. 2,5-dichloroaniline did not cause any chromosomal damage to V79 cells in the chromosome aberration test, it was not mutagenic in E. coli WP2uvrA, and it did not damage DNA in the UDS test on hepatic cells. Similarly, 3,4-dichloroaniline did not have any mutagenic activity in mammalian cells in the HGPRT test. A positive result was recorded in the fungus Aspergillus nidulans and in the pol A1- -test on E. coli. Several UDS tests on hepatic cells showed that 3,4-dichloroaniline did not damage DNA; one UDS test recorded a weak positive result. There was no increase in the frequency of sister chromatid exchanges in lymphocytes without metabolic activation, but an increase was observed when S9 mix was added. There was no indication of chromosomal damage in Allium cepa, in mammalian cells during the chromosome aberration test and in vivo in the mouse during the micronucleus test for 3,4-dichloroaniline. There are no studies on carcinogenicity. 3,4-dichloroaniline was not teratogenic inanimal experiments and was embryotoxic only at distinctly maternotoxic doses.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,4-Dichlorobenzeneamine is included on this list.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 2,4-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

The metabolism of four (14)C-labeled thiobis(formamidine) insecticides was studied in Sprague Dawley rats & ICR mice. The insecticides were derived from a series of 2,4-disubstituted anilines. The compounds studied included 2,4-dichloroaniline. Each compound was orally admin in corn oil solution to 2 female rats & 4 female mice in doses of 10-13 mg/kg. In every case, the corresponding anilines were detected as free aniline, in minor amounts except for the dichloro series. There were no significant differences observed between the compounds studied. The general metabolism schemes for all 4 compounds were similar. Metabolism of these compounds involves rapid hydrolysis of the parent compound in the stomach to simple formamidine, which is then converted to an N-formylaniline that has various metabolic fates, particularly through oxidation of methyl groups.

In order to reveal the urinary metabolites of p-chloronitrobenzene (CNB), an investigation was conducted to separate and identify urinary metabolites by gas chromatography/mass spectrometry following the administration of the compound to rats. Six male Sprague-Dawley-rats were given a single dose of 100 mg/kg CNB diluted in olive-oil and injected intraperitoneally. Urine was collected from the six rats at from 8 to 24 hours after exposure. Trace amounts of unchanged CNB were detected in the urine of the rats, but most of the CNB appeared to have been metabolized prior to excretion. Nine substances were identified: p-chloroaniline, 2,4-dichloroaniline, p-nitrothiophenol, 2-chloro-5-nitrophenol, 2-amino-5-chlorophenol, p-chloroformanilide, 4-chloro-2-hydroxyacetanilide, a small amount of p-chloroacetanilide and traces of unchanged CNB.

The urinary metabolites of p-chloronitrobenzene (p-CNB) in humans were determined using urine samples from acutely poisoned subjects. The six subjects were longshoremen hospitalized after being exposed to p-CNB while loading torn bags of the substance. Moment analysis and compartment model analysis of the urinary excretion rate of metabolites of p-CNB versus time curves were used for the pharmacokinetic evaluation. The findings suggest that the average values of the ratio of excreted amount of each metabolite to the total amount of the five metabolites and mean residence time in the six subjects were, respectively, 12.2% and 6.7 days for 2-chloro-5-nitrophenol (619103), 48.0% and 7.0 days for N-acetyl-S-(4-nitrophenyl)-L-cysteine, 1.2% and 3.7 days for 2,4-dichloroaniline, 29.9% and 10.0 days for p-chloroaniline, and 8.7% and 6.0 days for 2-amino-5-chlorophenol. The rates of transformation of p-CNB to 2-chloro-5-nitrophenol and p-chloroaniline appeared to be slow, but the resulting p-chloroaniline was metabolized relatively rapidly in the human body. The authors note that the ratio of the excretion amounts of the five metabolites was nearly constant among the subjects, whereas the rate of metabolism of the parent compound and the mean residence time varied widely among the individuals.

CHEM INTERMED FOR CI PIGMENT YELLOW 16; LABORATORY REAGENT

Intermediate in the production of pesticides, plastics, and dyes /Chlorinated anilnes/

2023: 500,000 - <1,000,000 lb

(1977) AT LEAST 4.54X10+5 G

(1981) NO EVIDENCE OF COMMERCIAL PRODUCTION IN USA

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Benzenamine, 2,4-dichloro-: ACTIVE