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Home > Encyclopedia > 3-Chloroaniline

3-Chloroaniline

3-Chloroaniline structure

3-Chloroaniline 

structure
  • CAS No:

    108-42-9

  • Formula:

    C6H6ClN

  • Chemical Name:

    3-Chloroaniline

  • Synonyms:

    Benzenamine,3-chloro-;Aniline,m-chloro-;3-Chlorobenzenamine;m-Chloroaniline;Fast Orange GC Base;3-Chloroaniline;m-Aminochlorobenzene;m-Chlorophenylamine;Orange GC base;1-Amino-3-chlorobenzene;3-Chlorophenylamine;3-Amino-1-chlorobenzene;3-Chloro-1-aminobenzene;NSC 17581;5-Chloroaniline;1083238-51-0

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

clear pale yellow to brown liquidColorless to light amber liquid with a sweet odor.


M-chloroaniline is a colorless to light amber liquid with a sweet odor. (NTP, 1992)|LIGHT YELLOW LIQUID WITH CHARACTERISTIC ODOUR. TURNS DARK ON EXPOSURE TO AIR.


M-chloroaniline is a colorless to light amber liquid with a sweet odor. (NTP, 1992)

3-Chloroaniline Basic Attributes

127.57

127.57

605969

203-581-0

6GKR52SKIY

0130

17581

2019

DTXSID0024761

Colorless to light amber, tends to darken during storage

29214210

Characteristics

26

1.9

Clear pale yellow to brown Liquid

1.2150 g/cm3 @ Temp: 22 °C

-10.4 °C

230.5 °C

255 °F

n 20/D 1.594(lit.)

H2O: 6.8 g/L (20 ºC)

Store below +30°C.

1 mm Hg ( 63.5 °C)

Relative vapour density (air = 1): 4.4

Oral-rat LD50: 256 mg/kg; Oral-Mouse LD50: 334 mg/kg

Combustible in case of open flame; burning produces toxic nitrogen oxides and chloride fumes

Characteristic sweet odor

10.00e-07 atm-m3/mole|Henry's Law constant = 1.0X10-6 atm-cu m/mol at 25 °C

pKa = 3.521 at 25 °C (conjugate acid)

Heat of decomposition was determined as zero.|Hydroxyl radical reaction rate constant = 7.6X10-11 cu cm/molec-sec at 25 °C /Estimated/

Sensitive to prolonged exposure to air and light and tends to darken during storage. Insoluble in water.

Aryl Halides

M-CHLOROANILINE is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. (NTP, 1992)

>540 °C

Safety Information

II

6.1

UN 2019 6.1/PG 2

2

23/24/25-33-50/53

28-36/37-45-60-61-28A

BX0350000

T,N

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

Toxic

Tends to darken during storage.

P261-P273-P280-P301 + P310-P311-P501

H301-H311-H331-H373-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Sakamoto Y, Watanabe S; Bull Chem Soc Jpn 59 (10): 3033-8 (1986). The relation between chem structure and carcinogenicity was investigated in 38 polycyclic aromatic cmpd and 44 chlorinated aromatic hydrocarbons by means of (13)C-NMR.

This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H301 (72.34%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P314, P320, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 188 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear butyl rubber gloves, protective plastic clothing and self-contained breathing apparatus.

Water, dry chemical, foam or carbon dioxide. /4-Chloroaniline/

Immediately wash contaminated areas of body with concentrated soap solution. Remove contaminated clothing, dry, then wash with concentrated soap solution or dispose as waste. Contaminated shoes may be disposed of in an incinerator.|...Precaution should be taken to avoid inhalation of vapors.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chloroanilines, liquid; Chloroanilines, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chloroanilines, liquid; Chloroanilines, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Chloroanilines, liquid; Chloroanilines, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chloroanilines, liquid; Chloroanilines, solid/|For more DOT Emergency Guidelines (Complete) data for 3-CHLOROANILINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

...Irritant on skin and mucous membranes.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from food and feedstuffs. Keep in the dark. Well closed.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes and skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.

The substance may have effects on the blood. This may result in the formation of methaemoglobin.

NO open flames.

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or face shield.

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. m-chloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

In a comprehensive survey of wastewater from 4,000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, 3-chloroaniline was identified in discharges of the following industrial category (positive occurrences, median concn in ug/L): organics and plastics (5; 96.7), soaps and detergents (1; 28.0), pharmaceuticals (6; 58.7), organic chemicals (3; 13.8), publicly owned treatment works (14; 2.6)(3). The highest effluent concn was 612 ug/L in the pharmaceutical industry(3). Unspecified isomers of chloroaniline have been detected in the effluent from the publicly owned treatment works (POTW) of Sauget, IL(1). 3-Chloroaniline has been qualitatively detected in effluent water concentrates collected in 1974 and 1975 from advanced waste treatment facilities in Pomona, CA(2).

3-Chloroaniline, which is the main metabolite of chloropropham, corresponded to about 50% of the applied dosage of chloropropham in the 2nd of 3rd successive lettuce cultures(1). After the 3rd culture, the amount of chloropropham and 3-chloroaniline increased in soil and lettuce(1).

SOURCE DOMINATED: Chloroaniline (isomer not specified) was detected at 0.033 ug/cu m in 1 of 8 air samples from industrial sites in the New Jersey area near American Cyanamide plant in Bound Brook(1).

Toxicity

highly toxic

LD50 Guinea pig oral 250 mg/kg|LD50 Cat dermal 223 mg/kg|LC50 Mouse inhalation 550 mg/cu m/ 4hr|LD50 Mouse oral 334 mg/kg|For more Non-Human Toxicity Values (Complete) data for 3-CHLOROANILINE (7 total), please visit the HSDB record page.

/AQUATIC SPECIES/ 21 day Daphnia reproduction tests were conducted in line with the provisional procedure proposed by the Federal Environmental Agency, as of Jan 1, 1984. Groups of 20, 24-hr old Daphnia magna Straus were exposed to 6.3 to 800 ug/L 3-chloroaniline in semi-static test vessels. Parent animals in the test and control vessels had to be pipetted 3 times/wk in freshly prepared test and control media at the corresponding concentration level. The no observed effect concentration (NOEC) was determined from the parameters of mortality of the parent animals, reproduction rate and appearance of the first offspring during the test period. In preliminary acute Daphnia tests, the 24 hr EC50 was 0.9 mg/L for 3-chloroaniline, the EC0 was 0.40 mg/L. The nominal 21 day no observed effect concn was 0.013 mg/L, with the more sensitive parameters being reproductive rate and the appearance of first offspring.

3-Chloroaniline's production and use as an intermediate for azo dyes and pigments, pharmaceuticals, insecticides, and agricultural chemicals(1) may result in its release to the environment through various waste streams(SRC). Chloroanilines may also form in the environment as degradation products of various pesticides(2). 3-Chloroaniline has been identified as a major degradation product of the herbicide chlorpropham during soil field studies(3). Release may also occur from alkaline hydrolysis of the herbicide barban(4) or the anaerobic biodegradation of 3,4-dichloroaniline under methanogenic, but not sulfate-reducing conditions(5), both of which results in the formation of 3-chloroaniline.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 3-chloroaniline is expected to have moderate mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). 3-Chloroaniline may undergo covalent chemical bonding with humic materials which results in its chemical alteration and tight adsorption(6). There is evidence to suggest that this complexing may extend the residual life of these substances in soil for as much as 10 years(7). Due to this covalent bonding, significant leaching in soil systems is not generally expected to occur(SRC). The pKa of 3-chloroaniline is 3.52(10), indicating that this compound will primarily exist in its nonionic form in the environment. Volatilization of 3-chloroaniline from moist soil surfaces is expected to occur(SRC) given a Henry's Law constant of 1.0X10-6 atm-cu m/mole(8). However, adsorption to soil is expected to attenuate volatilization(SRC). 3-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.066 mm Hg(9). 3-Chloroaniline may degrade in soil by chemical and microbial processes(11). When 3-chloroaniline (30 ppm) was incubated in Guelph loam with water added to 60% water-holding capacity, levels declined rapidly for 2 weeks after which time the rate of loss decreased(11). The percent of 3-chlororaniline remaining in soil after 2 and 8 weeks were 38% and 18%, respectively(11).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 3-chloroaniline may adsorb to suspended solids and sediment(SRC). In addition, 3-chloroaniline may undergo chemical bonding with humic materials in the water column and in the sediment(4). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.0X10-6 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 42 and 310 days, respectively(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(13,14), and volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The pKa of 3-chloroaniline is 3.52(6), indicating that this compound will primarily exist in its nonionic form in the environment. According to a classification scheme(7), measured BCF values ranging from 0.8 to 11.5(8,9) suggests the potential for bioconcentration in aquatic organisms is low(SRC). In a 3-day cultivation test using 2 different river waters from Japan and two different sea waters, 50% of initial 3-chloroaniline was degraded; the degradation was paralleled by growth of microbes(9,10). A biotransformation half-life of 0.4 year was determined for 3-chloroaniline in laboratory studies using two pond and one river water samples obtained near Athens, GA(12). Irradiation of an aqueous solution of 3-chloroaniline in a quartz tube with a fluorochemical lamp (wavelengths above 300 nm) resulted in a photodegradation half-life of 2.6 hours(14).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-chloroaniline, which has a vapor pressure of 0.066 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-chloroaniline 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 5.1 hours(SRC), calculated from its rate constant of 7.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3-Chloroaniline absorbs light with wavelengths >290 nm(4) and may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 3-chloroaniline with photochemically-produced hydroxyl radicals has been estimated as 7.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.1 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3-Chloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 3-Chloroaniline absorbs light with wavelengths >290 nm(3) and may be susceptible to direct photolysis by sunlight(SRC). Irradiation of an aqueous solution of 3-chloroaniline in a quartz tube with a fluorochemical lamp (wavelengths above 300 nm) resulted in a photodegradation half-life of 2.6 hours(4). The quantum yield was measured to be 0.0429 at 292 nm in hexane solution with photodegradation to aniline(5). In another study in which 3-chloroaniline in water was irradiated in a photoreactor with a light source with radiation in the 250-300 nm region (Integrated intensity times extinction coefficient = 3512 L/mol-cm, 20 °C), the photohydrolysis rate constant and half-life was 0.393/min and 1.76 min respectively(6). The quantum yield was 0.212 and independent of wavelength(6).

2.24|The average BCFs in the whole body of carp exposed to 3-chloroaniline in flow-through experiments (25 °C, 12 L/hr) for 24 to 336 hr at high (14.7 ug/L) and low (0.67 ug/L) exposure levels were 0.8 and 2.2, respectively(1). Excretion was rapid with depuration rates and half-lives of 0.21/hr and 3.3 hr, respectively(1). This conclusion is supported by field data in which the concentration of 3-chloroaniline in water and fish were <0.02 - 0.02 ug/L and <2.0 ng/g(1). Uptake was rapid in static tests (0.17 umol/L, 26 °C) on zebrafish and a BCF of 11.5 was obtained for 100 hr exposure (2). Elimination was best described by a two compartment first order model(2). After 52 hr of depuration, the concn of 3-chloroaniline in the zebrafish declined to 10.3% of the steady state value. According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 3-chloroaniline is estimated as 250(SRC), using a log Kow of 1.88(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-chloroaniline is expected to have moderate mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). In laboratory persistence studies using non-sterilized Hagerstown silty clay loam soil, 73% of applied 3-chloroaniline remained chemically bound to soil particles after 64 days of incubation(6). A related chemical, 2-chloroaniline, has 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 followed by oxidation of the product to give an amino-substituted quinone(7).

The Henry's Law constant for 3-chloroaniline is 1.0X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that 3-chloroaniline 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 42 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 310 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). 3-Chloroaniline's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization is expected to be attenuated by adsorption to soil(SRC). 3-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.066 mm Hg(3). In laboratory persistence studies using non-sterilized Hagerstown silty clay loam soil, 2.5% of applied 3-chloroaniline volatilized over a 49 day period(4).

DRINKING WATER: Unspecified drinking water in Germany has been reported to contain 3-chloroaniline(1). Maximum 3-chloroaniline levels of 1.0 ppb have been found in tapwater which uses bank-filtered Rhine River water as the source(2).|SURFACE WATER: 3-Chloroaniline was detected in 80% of all samples collected at a single site on the Rhine River in 1979 at mean, median, and maximum concns of 0.14, 0.06, and 1.8 ug/L, respectively(1). Mean, median, and maximum concns of 0.07-0.09, 0.05-0.06, and 0.21-0.45 ug/L, respectively, were found in two tributaries of the Rhine River in 1979(1). Mean, median, and maximum concns of 0.01-0.02, 0.02, and 0.06-0.09 ug/L, respectively, were found at two locations on the Meuse River in 1979(1). Concns of 3-chloroaniline in the Rhine River in 1982 have been reported to be below 0.1 ug/L(2). 3-Chloroaniline has been qualitatively identified in surface waters of the Rhine River Delta(3). 3-Chloroaniline was detected in 5 of 12 samples collected in 1992 from two sites on the River Elbe; concentrations ranged from 0.0022-0.0089 and 0.0032-0.01 ug/L at each site(4).|GROUNDWATER: 3-Chloroaniline was detected at 61 ug/L in only one sample of groundwater sampled from contaminated groundwater underneath a former industrial complex(1).

3-Chloroaniline was detected in several samples of potato peels, 0.18-0.36 ppb, from potatoes obtained from various geographic locations(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 851 workers (187 of these are female) are potentially exposed to 3-chloroaniline in the US(1). Occupational exposure to 3-chloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 3-chloroaniline is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 3-chloroaniline via ingestion of food and drinking water(SRC).

Drug Information

m-Chloroaniline is readily absorbed through the skin and also via the gastrointestinal tract and lung. .

3-Chloroaniline was excreted /by rats/ in urine as glucuronides and sulfate esters of 4-hydroxy-3-chloroacetanilide (a major metabolite) and 2-hydroxy-5-chloroacetanilide (a minor metabolite).|...In male albino rats after a single oral dose /of 3-chloroaniline/ urine was collected and analyzed. ...TLC showed the presence of 2-amino-4-chlorophenol and 4-amino-2-chlorophenol. ...Acetyl phenols were also identified /as were/ glucuronides and sulfates of the phenols and their acetyl derivatives. ...2-Amino-6-chlorophenol was not found but traces of the glucuronide and sulfate were. ...|Metabolites identified following oral administration of 150 mg/kg in rats: 2-amino-4-chlorophenyl-beta-d-glucuronide, 4-amino-2-chloro phenyl-beta-d-glucuronide, 4-acetylamino-2-chlorophenyl-beta-d-glucuronide, 2-acetylamino-4-chlorophenyl-beta-d-glucuronide, 2-amino-4-chlorophenylsulfate, 4-amino-2-chlorophenylsulfate, 2-acetylamino-4-chlorophenylsulfate, and 4-acetylamino-2-chlorophenylsulfate.|High performance liquid chromatography was used to quantify the metabolism of free chlorpham and its metabolites in isolated rat hepatocyte incubations. ... 10 percent was metabolized to 3-chloroaniline which was broken down to 3-chloroacetanilide. ...|For more Metabolism/Metabolites (Complete) data for 3-CHLOROANILINE (6 total), please visit the HSDB record page.

0.19 Days

SYMPTOMS: Symptoms of exposure to this chemical may include methemoglobinemia and, in large concentrations cyanosis; dermatitis, liver and kidney damage, and death. ACUTE/CHRONIC HAZARDS: This compound can cause allergic reactions. It is readily absorbed through the skin. When heated to decomposition it emits toxic fumes. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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.

Methylene blue, alone or in combination with oxygen, is indicated as treatment in nitrite-induced methemoglobinemia.|Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

/HUMAN EXPOSURE STUDIES/ In the United Kingdom between 1961 and 1980, chloroaniline, p-toluidine, nitrobenzene, and nitrochlorobenzene were the most common industrial causes of methemoglobinemia. Dermal exposure was a more frequent route of toxicity than inhalation with these compounds. /Chloroaniline/|/SIGNS AND SYMPTOMS/ Symptomatology: Lips, tongue and mucous membranes navy blue to black; skin slate gray, all without signs of cardiac or pulmonary insufficiency. Severe headache, nausea, sometimes vomiting, dryness of throat. Central nervous symptoms: confusion, ataxia, vertigo, tinnitus, weakness, disorientation, lethargy, drowsiness, and finally coma. Convulsions may occur but appear to be uncommon. Cardiac effects: heart blocks, arrhythmias, and shock. Death, although uncommon, is usually due to cardiovascular collapse and not resp paralysis. Urinary signs and symptoms may incl painful micturition, hematuria, hemoglobinuria, and renal insufficiency (usually mild). A late acute hemolytic episode should be anticipated at 6 to 8 days after ingestion. /Aniline/|/SIGNS AND SYMPTOMS/ Acute and long term exposure to m-chloroaniline leads to methemoglobin formation in humans... .

3-chloroaniline

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

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


MAY BE ABSORBED! Redness. Burning sensation. Further see Inhalation.


Redness. Pain.

3-Chloroaniline Use and Manufacturing

Methods of Manufacturing

The preparation method is obtained by reduction of m-chloronitrobenzene. The reducing agent can be sodium sulfide or zinc powder and hydrochloric acid. In the reaction kettle, sodium sulfide is dissolved in water, stirred and heated to boiling, and gradually added human chloronitrobenzene, refluxed for 5 h Afterwards, distill the oily liquid to get the finished product.

Uses

3-Chlorobenzenamine is used in the synthesis of pyrimidoazepine analogs as serotonin 5-HT2A and 5-HT2C receptor ligands for the treatment of obesity. Also used in the synthesis of novel COX-2 inhibitors.

GRADES: Technical

Benzenamine, 3-chloro-: ACTIVE

THIS METHOD DETECTS ANILINE DERIVATIVES FORMED AS DEGRADATION PRODUCTS FROM CERTAIN PESTICIDES USING THIN-LAYER CHROMATOGRAPHY.|HPLC METHOD WITH UV DETECTION WAS DEVELOPED FOR THE DETECTON OF SUB-NG QUANTITIES OF HALOGENATED ANILINE DERIVATIVES.|SEPARATION OF UREA HERBICIDES & CHLORANILINES BY HPLC. IT IS POSSIBLE TO SEPARATE UREA CMPD FROM CHLORANILINE, OCCURRING OFTEN AS METABOLITES OF FORMER, BY HIGH-PRESSURE LIQ CHROMATOGRAPHY.|AN ANALYTICAL METHOD WAS PRESENTED FOR THE GAS CHROMATOGRAPHIC DETERMINATION OF MONOCHLOROANILINES AND THEIR DERIVATIVES IN SURFACE WATER.|Method: 8131; Procedure: gas chromatography with nitrogen-phosphorus detector; Analyte: 3-chloroaniline; Matrix: aqueous matrices; Detection Limit: 1.8 ug/L.

DETERMINATION OF HALOGENATED ANILINES IN URINE BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY WITH AN ELECTROCHEMICAL DETECTOR.|A simple gas liquid chromatographic method has been developed which provides sensitivity and specificity for the analysis of complex mixtures of the commonly occurring herbicide metabolites aniline, 3-chloroaniline, 4-chloroaniline, 4-bromoaniline, and 3-chloro-4-methylaniline. All of these anilines react with acetic anhydride directly in basified aqueous solution. Further reaction of the acetylated anilines with trifluoroacetic anhydride gave diacyl derivatives which were readily resolved by gas chromatography. The technique was applied to the determination of anilines added to urine samples.

Computed Properties

Molecular Weight:127.57
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:127.0188769
Monoisotopic Mass:127.0188769
Topological Polar Surface Area:26
Heavy Atom Count:8
Complexity:74.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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