2,5-Dichloroaniline

log Kow= 2.92

2.75

1.54 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.01

Light brown or amber-colored crystalline mass

NEEDLES FROM PETROLEUM ETHER

less than 1 mg/mL at 72.5 °F (NTP, 1992)

Sol in dilute hydrochloric acid

Slightly soluble in water; soluble in ethanol, ethyl ether, banzene

Solubility in water: none

235 °F (NTP, 1992)

139 °C

139 °C

484 °F at 760 mmHg (NTP, 1992)

251 °C

251 °C

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

380 °C. Decomposes on burning. This produces toxic fumes including nitrogen oxides and hydrogen chloride (see ICSC 0163).

120 to 124 °F (NTP, 1992)

50 °C

50 °C

This chemical does not meet GHS hazard criteria for 0.5% (1 of 201) of reports.

Danger

H301+H311+H331 (19.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

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 201 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: Benzenamine, 2,5-dichloro-

Status: Active Update: 10-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/6125

2,5-Dichloroaniline: Does not have an individual approval but may be used under an appropriate group standard

This chemical is 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.

Causes flaccid paralysis, cyanosis, and convulsions in lethal-dose studies of guinea pigs and rabbits; [RTECS] Emergency treatment: Methemoglobinemia; [HSDB] A severe eye irritant; Can induce methemoglobinemia; May cause skin sensitization; [ICSC] A skin, eye, and mucous membrane irritant; [CAMEO]

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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,5-Dichlorobenzeneamine is included on this list.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. 2,5-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

Fires involving this compound should 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. NO direct contact 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, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol 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 alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate 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. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

... 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/

In the case of /skin/ contact it should be washed for a long time with soap & tepid water. When eyes are /exposed to aniline/ copious irrigation with water is immediately necessary. ... /Aniline/

For more Preventive Measures (Complete) data for 2,5-DICHLOROANILINE (8 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 355(2) indicates that 2,5-dichloroaniline is expected to have moderate mobility in soil(SRC). However, when released to soil containing humic material, 2,5-dichloroaniline may undergo a covalent chemical bonding resulting in its chemical alteration to a latent form resulting in strong adsorption(3). 2,5-Dichloroaniline demonstrated almost a linear rate of decomposition in Guelph loam over a 12 week period, with a half-life of 8 weeks(4). Volatilization of 2,5-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(5). 2,5-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(6).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 355(2) indicates that 2,5-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 2,5-dichloroaniline since it does not take into account the effects of adsorption. The Koc of 355(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, yielding an estimated half-life of 662 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(5). According to a classification scheme(6), an estimated BCF of 35(3,SRC), from a log Kow value of 2.92(2), suggests the potential for bioconcentration in aquatic organisms is moderate.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semi-volatile organic compounds in the atmosphere(1), 2,5-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 2,5-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 17 hours(SRC) from its estimated rate constant of 2.2X10-12(3).

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

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain. Blurred vision.

Abdominal pain. Further see Inhalation.

The Koc for 2,5-dichloroaniline is 355(1). According to a classification scheme(2), this Koc value suggests that 2,5-dichloroaniline is expected to have moderate mobility in soil. However, when released to soil containing humic material, 2,5-dichloroaniline may undergo a covalent chemical bonding resulting in its chemical alteration to a latent form resulting in strong adsorption(3).

2,5-Dichloroaniline's production and use as a dye intermediate(1) may result in its release to the environment through various waste streams(SRC). Aromatic amines such as 2,5-dichloroaniline are introduced into the environment directly as industrial effluents and indirectly as transformation products from pesticides or pharmaceuticals(2). 2,5-Dichloroaniline has been identified as a degradation product of Acid Dye 13155(3).

The effects of dichlorine-substituted anilines on Guelph loam were studied. 2,5-Dichloroaniline at concentrations of 5 to 100 ug/g soil was inhibitory against the oxidation of the nitrogen of ammonia to nitrite nitrogen, but not nitrite nitrogen to nitrate nitrogen. It showed almost a linear rate of decomposition over the 12 wk period of the expt. The dichloroanilines were more persistent than aniline or the monochloroanilines.

2,5-Dichloroaniline demonstrated almost a linear rate of decomposition in Guelph loam over a 12 week period, with a half-life of 8 weeks(1). 2,5-Dichloroaniline has been classified as resistant to biodegradation (theoretical BOD of less than 30% over a 14-day incubation period using an activated sludge inocula) using the Japanese MITI test protocol(2-4). 2,5-Dichloroaniline, present at 100 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(5). Using the modified OECD Screening Test (activated sludge inocula, 28 days aerobic incubation), less than 25% of initial 2,5-dichloroaniline was degraded based on DOC analysis(6). Using the modified AFNOR Test (28 days of incubation), 7% of initial 2,5-dichloroaniline was degraded based on DOC analysis(6).

An estimated BCF of 35 was calculated for 2,5-dichloroaniline(SRC), using log Kow of 2.92(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.

The Henry's Law constant for 2,5-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 2,5-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 30 days(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 of 355(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 662 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). 2,5-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,5-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).

IN GUELPH LOAM, 2,5-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.

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/

Dichloroaniline produces methemoglobinemia in rats & mice. /Dichloroaniline/

The rate constant for the vapor-phase reaction of 2,5-dichloroaniline with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 2,5-dichloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum.

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. 2,5-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. 2,5-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

The metabolic fate of propanil in plants was studied. The conversion of this compound in soil to 3,3',4,4'-tetrachloroazobenzene is catalyzed by soil peroxidases. This reaction also occurs in the presence of crystalline horseradish peroxidase. In some plants propanil is rapidly hydrolyzed to give 3,4-dichloroaniline. Crude extracts of barnyard grass, fresh horseradish root, rice & commercially purified crystalline horseradish enzyme were prepared. It was inferred that the differences in substrate specificity among peroxidases may account for the failure of some plants to convert the aniline to azo compounds such as in the conversion to 3,4-dichloroaniline to 3,3',4,4'-tetrachloroazobenzene. ... Enzymatically catalyzed products of mono- & dichloroanilines were prepared by mixing barnyard grass supernatants or horseradish peroxidase with an acetic buffer, hydrogen peroxide & various aniline substrates & allowed to react for 30 min. Preparations made from fresh horseradish & from horseradish peroxidase gave products with all anilines except 2,5- & 2,6-dichloroanilines. Barnyard grass & rice plants gave products only with 2,3-dichloroaniline of the dichloroaniline substrates studied. /Dichloroanilines/

Used as a chemical intermediate for dyes and pigments and to make dyed fibers more color-fast; [HSDB]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Dye intermediate

CHEM INT FOR PIGMENTS (SUCH AS CI PIGMENT RED 2 & 9), AND FOR AZOIC DIAZO COMPONENT 3, SALT

Used in the after treatment process to dye fibers making them more color-fast by coupling with direct dyes after the direct dye has become exhausted.

(1979) 1.63X10+8 G (PRINCIPAL CUSTOMS DISTRIBUTORS)

(1981) 1.02X10+8 G (PRINCIPAL CUSTOMS DISTRIBUTORS)

(1983) 8.1X10+4 lb

Nitration of para-dichlorobenzene with subsequent reduction.

NITRATION & REDUCTION OF 1,4-DICHLOROBENZENE USING EITHER IRON & HYDROCHLORIC ACID OR CATALYTIC HYDROGENATION

Hydrogenation of halide-substituted nitro compounds using sulfide-poisoned metal catalysts.