2,3-Dichloroaniline

Nitrogen Compounds -> Amines, Aromatic

Textile

log Kow= 2.78

2.78

2.51

1.383 @ 25 °C

Relative density (water = 1): 1.383

VERY SOL IN ETHER; SLIGHTLY SOL IN PETROLEUM ETHER, BENZENE

Sol in alcohol, acetone

Solubility in water: none

>112 °C (closed cup)

>112 °C c.c.

252 °C

252 °C

24 °C

24 °C

0.02 [mmHg]

Vapor pressure, Pa at 25 °C:

Danger

H301+H311+H331 (34.9%): 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, P332+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 83 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Danger

Chemical: Benzenamine, 2,3-dichloro-

Status: Active Update: 14-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/11877

Benzenamine, 2,3-dichloro-: Does not have an individual approval but may be used under an appropriate group standard

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

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

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Causes somnolence, tremor, and weight loss in inhalation lethal-concentration studies of rats; [RTECS] Eye contact can cause redness and pain; May induce methemoglobinemia; Can be absorbed through skin; [ICSC] An irritant that may cause serious eye injury; May cause skin sensitization; Toxic by ingestion, inhalation, and skin absorption (may induce methemoglobinemia); Suspected mutagen and carcinogen; [ECHA REACH Registrations] An irritant; May induce methemoglobinemia; Highly toxic by ingestion, inhalation, and skin absorption; [Alfa Aesar MSDS] See 3,4-Dichloroaniline.

3442 153

1590 153

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. 2,3-Dichlorobenzeneamine is included on this list.

A halogenated aromatic amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

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 .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

General First Aid:

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

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/

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. Collect leaking and spilled liquid in sealable containers as far as possible. 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 2,3-DICHLOROANILINE (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 2,3-dichloroaniline is expected to have high mobility in soil(SRC). When released to soil, 2,3-dichloroaniline may undergo covalent chemical bonding with humic materials, which can result in its chemical alteration to a latent form and tight adsorption. When covalently bound in this latent form, leaching in soil systems is not generally expected to occur. This covalent bonding proceeds in two steps; a rapid and reversible bonding followed by a slower and much less reversible reaction(3). The effects of dichlorine-substitued anilines on guelph loam were studied under aerobic conditions. It was shown that a linear rate of decomposition over a 12 week period existed for these compounds(4). Volatilization of 2,3-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). 2,3-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-2 mm Hg(SRC), determined from a fragment constant method(6). Due to the strong adsorption to humic material in the soil, 2,3-dichloroaniline volatilization is expected to be attunuated(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 2,3-dichloroaniline is not expected to adsorb to suspended solids and sediment in water(SRC). By analogy to other chloro- and dichloroaniline isomers(3), 2,3-dichloroaniline may undergo covalent bonding with humic materials in the water column and in sediment; partitioning from the water column to sediment and suspended material may therefore be important(3). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC) developed using a fragment constant estimation method(5). Volatilization half-lives for a model river and model lake are 30 and 219 days, respectively(SRC), using an estimation method(4). 2,3-Dichloroaniline may undergo a covalent chemical bonding with suspended soil particles resulting in its chemical alteration to a latent form resulting in strong adsorption, attenuating volatilization(6). According to a classification scheme(7), an estimated BCF of 76(4,SRC) suggests the potential for bioconcentration in aquatic organisms is moderate. The first-order rate constant for 2,3-dichloroaniline degradation a sediment slurry was 0.013 day-1 with a half-life of 54 days under anaerobic conditions(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-dichloroanilne, which has an estimated vapor pressure of 2.5X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3-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 2.2X10-2 cu cm/molecule sec(3).

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

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

Abdominal pain. Further see Inhalation.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,3-dichloroaniline can be estimated to be about 120(SRC). According to a classification scheme(2), this Koc value suggests that 2,3-dichloroaniline is expected to have high mobility in soil(SRC). 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 structure followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(3).

2,3-Dichloroaniline's production and use as intermediates in dyestuffs, pesticides, and pharmaceuticals(1) may result in its release to the environment through various waste streams. The chemical and biological reduction of azo dyes and halogenated nitroaromatic herbicides, explosives, and nitropyrenes could result in the formation of chloroaniline compounds in the environment(2).

The effects of dichlorine-substituted anilines on guelph loam were studied. Several dichloroanilines 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 experiment. The dichloroanilines were more persistent than aniline or the monochloroanilines. /Dichloroanilines/

AEROBIC: The effects of dichlorine-substitued anilines on guelph loam were studied under aerobic conditions. It was shown that a linear rate of decomposition over a 12 week period existed for these compounds(1). Incubation of 2,3-dichloroaniline in covered beakers containing a sandy loam soil for 14 days yielded the azo compound 3,4'-dichloroazobenzene; no azo compounds were detected in control incubations using sterilized soil(2). Products other than azo compounds were not isolated or analyzed(2). ANAEROBIC: A study of a sediment slurry taken from an anaerobic estuary collected from the mouth of the Tsuiami River, Japan, revealed that 2,3-dichloroaniline degraded to 3-chloroaniline and further to aniline(3). The first-order rate constant for 2,3-dichloroaniline degradation slurry was 0.013 day-1 with a half-life of 54 days under anaerobic conditions(3). This site has been well characterized and designated as a sulfate-reducing environment based on its sulfate concentration. This supports the idea that dechlorination of chloroanilines occurred under sulfate-reduction(3).

An estimated BCF of 76 was calculated for 2,3-dichloroaniline(SRC), using the log Kow of 2.78(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 2,3-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 2,3-dichloroaniline is expected to volatilize from water surfaces(2). 2,3-Dichloroaniline may undergo a covalent chemical bonding with suspended humic material resulting in its chemical alteration to a latent form resulting in strong adsorption, attenuating volatilization(3). 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). 2,3-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,3-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-2 mm Hg(SRC), determined from a fragment constant method(4).

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, 3,5-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. /DICHLOROANILINES/

Dichloroaniline produces methemoglobinemia in rats & mice. /Dichloroaniline/

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. 2,3-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. 2,3-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 dichloroaniline to 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.

Byproduct of 3,4-dichloroaniline production; Used in dyestuffs, pesticides, pharmaceuticals, and as a research chemical; [HSDB] Used as an intermediate; [ECHA REACH Registrations]

RESEARCH CHEMICAL

Dyestuffs, pesticides and pharmaceuticals.