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Home > Encyclopedia > 4-Chloro-2-methylaniline

4-Chloro-2-methylaniline

4-Chloro-2-methylaniline structure

4-Chloro-2-methylaniline 

structure
  • CAS No:

    95-69-2

  • Formula:

    C7H8ClN

  • Chemical Name:

    4-Chloro-2-methylaniline

  • Synonyms:

    Benzenamine,4-chloro-2-methyl-;o-Toluidine,4-chloro-;4-Chloro-2-methylbenzenamine;Daito Red Base TR;Fast Red Base TR;Fast Red 5CT Base;Fast Red TR Base;Fast Red TRO Base;Kako Red TR Base;Mitsui Red TR Base;Red Base NTR;Red TR Base;Sanyo Fast Red TR Base;4-Chloro-o-toluidine;2-Methyl-4-chloroaniline;2-Amino-5-chlorotoluene;4-Chloro-2-toluidine;4-Chloro-2-methylaniline;p-Chloro-o-toluidine;4-Chloro-6-methylaniline;3-Chloro-6-aminotoluene;Fast Red TR-T Base;5-Chloro-2-aminotoluene;2-Methyl-4-chlorobenzenamine;NSC 4979;(4-Chloro-2-methylphenyl)amine

  • Categories:

    Analytical Chemistry  >  Standard

Description

clear brown liquid The chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.


4-chloro-o-toluidine is a gray to white solid with a weak fishy odor. Sinks in water. Freezing point is 77°F. (USCG, 1999)|COLOURLESS TO BROWN SOLID IN VARIOUS FORMS OR LIQUID


4-chloro-o-toluidine is a gray to white solid with a weak fishy odor. Sinks in water. Freezing point is 77°F. (USCG, 1999)|4-Chloro-ortho-toluidine is a member of monochlorobenzenes.|p-Chloro-o-toluidine is a yellowish to pinkish colored, synthetic leaflet material. p-Chloro-o-toluidine is used in industry in the manufacture of azo dyes and is used in the production of the pesticide chlordimeform. This substance is a possible mutagen and is reasonably anticipated to be a human carcinogen that may be associated with an increased risk of bladder cancer. (NCI05)

4-Chloro-2-methylaniline Basic Attributes

141.6

141.60

202-441-6

95NB978426

0630

4979

2239

DTXSID1041508

C44431

Crystalline, fused, grayish-white solid (commercial product)|LEAVES FROM ALCOHOL

2921430090

Characteristics

26

2.27

4-chloro-o-toluidine is a gray to white solid with a weak fishy odor. Sinks in water. Freezing point is 77°F. (USCG, 1999)

>1.1 (estimated)

30 °C

241 °C @ Press: 760 Torr

211 °F

1.585

Solubility in water, g/100ml at 25°C: 0.095 (very poor)

2-8°C

Vapour pressure, Pa at 25°C: 5.5

Relative vapour density (air = 1): 4.9

pKa = 3.85 @ 25 °C

May be sensitive to prolonged exposure to air and light. Insoluble in water.

Aryl Halides

4-CHLORO-O-TOLUIDINE is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. (NTP, 1992). A halide- and amine-substituted aromatic compound. 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.

560 °C

Safety Information

III

6.1(b)

UN 2239 6.1/PG 3

3

45-23/24/25-50/53-68

53-45-60-61

XU5000000

T,N

Cool. Separated from food and feedstuffs. See Chemical Dangers. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

Stable under normal temperatures and pressures.

P201-P261-P273-P280-P301 + P310-P311

H301-H311-H331-H341-H350-H410

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.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for 4-CHLORO-O-TOLUIDINE (6 total), please visit the HSDB record page.

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. p-Chloro-o-toluidine (95-69-2) and p-Chloro-o-toluidine Hydrochloride are listed as reasonably anticipated to be human carcinogens. /p-Chloro-o-toluidine and p-Chloro-o-toluidine Hydrochloride/[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s043pcot.pdf]

Special Hazards of Combustion Products: Toxic oxides of nitrogen and hydrochloric acid fumes may form. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H301 (97.78%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P280, P281, P301+P312, P302+P352, P307+P311, P308+P313, P312, P314, P321, P322, P330, P363, P405, and P501

Fire Extinguishing Agents: Water, dry chemical (USCG, 1999)|Use water spray, dry powder, carbon dioxide.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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. (NTP, 1992)

Dust respirator; goggles; rubber gloves; protective clothing. (USCG, 1999)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for 4-CHLORO-O-TOLUIDINE (9 total), please visit the HSDB record page.

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. 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. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. Ventilate enclosed areas. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|For more DOT Emergency Guidelines (Complete) data for 4-CHLORO-O-TOLUIDINE (8 total), please visit the HSDB record page.

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.|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.

Sweep spilled substance into covered containers. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.

Cool. Separated from food and feedstuffs. See Chemical Dangers. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

May cause mechanical irritation to the skin, respiratory tract and eyes (as a solid). The substance may cause effects on the bladder. This may result in haemorrhagic inflammation. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

May cause heritable genetic damage to human germ cells.

NO open flames.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection if powder.

An industrial process wastewater from a petrochemical complex in Japan(1) contained 110 mg/l 4-chloro-o-toluidine(1).

(14)C-LABELED 4-CHLORO-O-TOLUIDINE WAS ADDED TO NONAUTOCLAVED SOIL & INCUBATED FOR 6 WK. CARBON DIOXIDE COULD BE DETECTED IN AMT OF 20.0% OF ORIGINALLY APPLIED RADIOACTIVITY.|Residues of chlordimeform and its metabolites were measured in ... paddy soil following experimental field application (one to three treatments, with harvesting 42 days after the last treatment). Residue concentrations of para-chloro-ortho-toluidine were ... 2-68 ppb (ug/kg) in the upper layer of soil (0-5 cm) and from trace to 20 ppb in the lower layer of soil (5-10 cm) ... .

Toxicity

A bioassay of 4-chloro-o-toluidine hydrochloride for possible carcinogenicity was conducted by admin the test chemical in feed to F344 rats and B6C3F1 mice Groups of 50 rats of each sex were admin 4-chloro-o-toluidine in the diet at one of two doses, either 1,250 or 5,000 ppm, for 107 wk. Groups of 50 mice of each sex were admin the test chemical in the diet at one of two doses, either 3,750 or 15,000 ppm for the males and either 1,250 or 5,000 ppm for females, for 99 wk, except for the high dose females (92 wk). Matched controls consisted of 20 untreated rats and 20 untreated mice of each sex. All surviving animals were killed at the end of admin of the test chemical. It is concluded that under the conditions of this bioassay, 4-chloro-o-toluidine hydrochloride was not carcinogenic for F344 rats but was carcinogenic for B6C3F1 mice, including hemangiosarcomas and hemangiomas in both males and females. ... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Positive; Female Mice: Positive.

... para-chloro-ortho-toluidine can be formed from chlordimeform, an insecticide and acaricide, by enzymes present in the leaves of apple seedlings ... as well as those of cotton plants ... .|4-Chloro-o-toluidine is produced for use in the production of azo dyes. It is also used as an intermediate for the production of pigments and for chlordimeform, a pesticide(1). The occurrence of 4-chloro-o-toluidine in the environment can be attributed to microbial and/or chemical degradation and photo-decomposition of various pesticides(2). 4-Chloro-o-toluidine is a photochemical degradation product of the acaricide, N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine (Galedron)(3).

TERRESTRIAL FATE: Photolysis of 4-chloro-o-toluidine on soil surfaces may occur; 4-chloro-o-toluidine spotted onto silica gel plates and exposed to sunlight resulted in 10 photolytic degradation products(1). An estimated Koc value of 410(2,SRC) indicates that 4-chloro-o-toluidine should have moderate mobility in soil(SRC), based upon a recommended classification scheme(3). In an experimental soil system, however, it was shown that a considerable portion, about 50%, of this compound bound very strongly to the soil medium and that this was possibly due to interactions between the aromatic amine and humic/organic materials in the soil(4,5); soils with very little organic matter may not bind 4-chloro-o-toluidine strongly(5,SRC). Biodegradation of 4-chloro-o-toluidine may occur and may be a major fate process of this compound in soil; 20% mineralization of 4-chloro-o-toluidine in soil was reported over a 6 week time period(6). A polymerizing transformation of 4-chloro-o-toluidine to the corresponding azobenzene was shown in the presence of pure enzymes derived from a soil fungus(7).|AQUATIC FATE: As 4-chloro-o-toluidine has an absorption maximum at a wavelength of 296 nm(1), it will absorb radiation from natural sunlight and may degrade photolytically(SRC). 4-Chloro-o-toluidine in ethanol solution exposed to short wavelength UV light gave a mixture of photolytic degradation products(2). Volatilization of 4-chloro-o-toluidine from water surfaces will be slow based on an estimated Henry's Law constant of 2X10-6 atm-cu m/mole(3,SRC). Sorption of this compound to organic material in the water column may be a significant fate process; soil with added 4-chloro-o-toluidine retained about 50% of this compound as a strongly bound residue following Soxhlet extraction(4,5). Interaction of the aromatic amine with organic matter in the soil was believed to be responsible for this binding(4,5). Biodegradation of this compound in water may be possible; from an industrial wastewater 7% removal of TOC was seen but with GC analysis, structural changes to this compound were also detected resulting in higher levels of measured biodegradation of the parent compound(6). Bioconcentration of 4-chloro-o-toluidine in aquatic organisms is not an important fate process(7).|ATMOSPHERIC FATE: Based on an estimated vapor pressure of 0.04 mm Hg at 25 °C(1,SRC), 4-chloro-o-toluidine will exist primarily in the vapor phase in the ambient atmosphere(2,SRC). 4-Chloro-o-toluidine will degrade by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 9 hours(3,SRC). Direct photolysis of 4-chloro-o-toluidine in the atmosphere may be possible(SRC) as indicated by experiments where 4-chloro-o-toluidine spotted onto silica gel plates and exposed to sunlight resulted in about 10 photolytic degradation products(4).

4-Chloro-o-toluidine was spotted onto a silica gel plate and irradiated with sunlight for 10 hours; radioautography revealed at least 10 products which were not identified(1). 4-Chloro-o-toluidine in solution with 95% ethanol was exposed to short wavelength UV light (253.7 mu at 23 cm with an intensity of 260 uw/sq cm) for time intervals up to 48 hours. A pronounced change in the UV-visible absorption spectrum occurred with the intense absorption throughout the visible region indicative of the formation of numerous decomposition products(1). The rate constant for the vapor-phase reaction of 4-chloro-o-toluidine with photochemically produced hydroxyl radicals has been estimated as 41.4X10-12 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2,SRC). An experimental pKa of 3.85 was measured for 4-chloro-o-toluidine(3). For most environmental pH conditions 4-chloro-o-toluidine will exist in the dissociated form(SRC).

34.67|Bioconcentration of 4-chloro-o-toluidine was measured in carp over a 6 week time period. At concentrations of 0.34 mg/ml and 0.034 mg/ml 4-chloro-o-toluidine, BCF values of 7.7-12 and <35 respectively, were reported(1). These values suggest that bioconcentration of 4-chloro-o-toluidine in aquatic organisms is not an important fate process for this compound(SRC).

The Koc for 4-chloro-o-toluidine was estimated as 410(SRC), using a recommended regression-derived equation(1) and an estiamted log Kow of 2.27(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that 4-chloro-o-toluidine has moderate mobility in soil(SRC). 14C labelled 4-chloro-o-toluidine was added to autoclaved soil (pH 7.5, and organic matter, sand, silt, and clay contents of 3.4, 36.6, 28.2, and 35.2%, respectively) and incubated for several weeks; 12.2% of the radioactive label was removed as volatiles, 25% was recovered in a Soxhlet extract, and 55.1% of the radioactive label was obtained after Soxhlet extraction using Bleidner distillation (bound residue fraction)(4). This suggests that a significant portion of the 4-chloro-o-toluidine is bound strongly by this soil(4). Over a 24 hour time period, 34% of applied 4-chloro-o-toluidine was found in the bound residue fraction(5). Binding due to the high reactivity of the aromatic amino group to humus or soil organic matter rather than to clay particles is proposed as a reason for the soil binding ability of anilines(4,5). Low adsorption is observed at a neutral pH with pure clay minerals or soils for substituted anilines(5).

The Henry's Law constant for 4-chloro-o-toluidine was estimated as 2X10-6 atm-cu m/mole using a structure estimation method(1,SRC). This value indicates that volatilization of 4-chloro-o-toluidine from water proceeds slowly(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec with a wind velocity of 3 m/sec) is 22 days(2,SRC). The volatilization half-life from a model environmental lake (1 m deep) is estimated as 163 days(2,SRC).

Exposures were reported to occur during the charging of mixing vats and the basification stage at a para-chloro-ortho-toluidine purification plant in the UK ... Workers in a batch-operated chemical processing plant ... in the USA were reported to be exposed by inhalation and dermal contact ... Workers were also reported to be exposed ... during its production and processing at a plant in the Federal Republic of Germany ... .|Routes of exposure to aromatic amines include respiratory exposure and direct skin contact(1).

4-Chloro-o-toluidine was detected in the urine of workers in Australia exposed to N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine, as a metabolic breakdown product of the acaricide; reverse-phase HPLC with UV detection has a detection limit of 0.4 to 10 ug/ml of 4-chloro-o-toluidine(1).

Drug Information

Colorless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into colored compounds; used in biochemical assays and in diagnosis as indicators, especially in the form of enzyme substrates. Synonym: chromogens (not to be confused with pigment-synthesizing bacteria also called chromogens). (See all compounds classified as Chromogenic Compounds.)

(14)C-LABELED 4-CHLORO-O-TOLUIDINE, WHEN ORALLY ADMIN TO WHITE RATS, WAS DEGRADED AND ELIMINATED PRIMARILY IN URINE ALONG WITH RADIOACTIVE METABOLITES. RATE OF ABSORPTION & DEGRADATION WAS SLOWER THAN FOR CHLORDIMEFORM.|para-Chloro-ortho-toluidine has been detected in the urine of workers exposed to chlordimeform ... .|Following oral administration of ((14)C-methyl)-para-chloro-ortho-toluidine to male and female white rats, 71% of the administered radioactivity was eliminated in the urine and 24% in the faeces within 72 hr ... .|Binding of para-chloro-ortho-toluidine to hemoglobin was observed after oral administration of 85 mg/kg bw to female Wistar rats ... .|RADIOACTIVITY FROM 4-CHLORO-2-METHYLANILINE-METHYL-(14)C WAS EXTENSIVELY BOUND TO PROTEIN, DNA, AND RNA OF RAT LIVER. ENZYMIC ACTIVITY DEPENDENT UPON NADH & LEADING TO IRREVERSIBLE BINDING OF RADIOACTIVITY FROM LABELED CMPD TO MACROMOLECULES WAS PRESENT IN MICROSOMES.

...CAN BE FORMED FROM CHLORDIMEFORM, AN INSECTICIDE AND ACARICIDE, BY ENZYMES PRESENT IN THE LEAVES OF APPLE SEEDLINGS...AS WELL AS THOSE OF COTTON PLANTS...|OVER 97% OF (14)C-LABELED CHLORDIMEFORM APPLIED TO PRIMARY HUMAN EMBRYONIC LUNG CELLS IN CULTURE WAS CHANGED AFTER 72 HR OF INCUBATION, WITH MAJOR METABOLITES APPEARING AS N-FORMYL-4-CHLORO-O-TOLUIDINE (81.9%) AND 4-CHLORO-O-TOLUIDINE (2.3%).|RATS DEGRADED CHLORDIMEFORM INTO N-(4-CHLORO-2-METHYLPHENYL)-N'-METHYLFORMAMIDINE, N-FORMYL-4-CHLORO-2-METHYLANILINE, 4-CHLORO-2-METHYLANILINE, AND 5 OTHER UNKNOWN METABOLITES.|FORMS 4,4'-DICHLORO-2,2'-DIMETHYLAZOBENZENE IN HORSERADISH. /FROM TABLE/|For more Metabolism/Metabolites (Complete) data for 4-CHLORO-O-TOLUIDINE (7 total), please visit the HSDB record page.

Inhalation, ingestion, or skin contact causes bluish tint in fingernails, lips, and ears. Headache, drowsiness, and nausea also occur. Contact with eyes causes irritation. (USCG, 1999)|Carcinogens

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)


Fresh air, rest. Refer immediately for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.


Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.

...HEMATURIA MAY BE OBSERVED IN MEN HANDLING...CHLORTOLUIDINES. ...MAY BE A HEMORRHAGIC CYSTITIS WITH PAINFUL & FREQUENT MICTURITION. THIS ACUTE PROBLEM IS OF NO LONG-TERM SIGNIFICANCE & CLEARS...ON CESSATION... IF HEMATURIA PERSISTS...OTHER PATHOLOGICAL URINARY TRACT PHENOMENA...CONSIDERED. /CHLOROTOLUIDINES/|...GROUP OF 35 MEN WHO PREPARED PARA-CHLORO-ORTHO-TOLUIDINE FROM ORTHO-TOLUIDINE DURING THE YEARS 1924-1953; NO BLADDER TUMORS WERE FOUND AMONG THESE MEN...|PARA-CHLORO-ORTHO-TOLUIDINE INHIBITED RNA SYNTHESIS IN HELA CELLS...|THE TOLUIDINES...MAY PRODUCE TRANSIENT HEMATURIA AS WELL AS METHEMOGLOBINEMIA AFTER HEAVY EXPOSURES, BUT THE CHLORO-DERIVATIVES ARE MORE POTENT IN THIS RESPECT... /CHLORO-TOLUIDINES/|For more Human Toxicity Excerpts (Complete) data for 4-CHLORO-O-TOLUIDINE (8 total), please visit the HSDB record page.

4-chloro-2-methylaniline

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

Cough. Red urine. Frequent, sudden and painful urination. Abdominal pain. Blue lips, fingernails and skin. Headache. Dizziness. Nausea. Drowsiness.


Redness. MAY BE ABSORBED! See Inhalation.


Redness. Pain.

4-Chloro-2-methylaniline Use and Manufacturing

Methods of Manufacturing

It is derived from o-toluidine through chlorination. There are many chlorination methods. O-toluidine hydrochloride uses chlorobenzene as the solvent, and reacts with chlorine at 50-60℃ to obtain 4-chloro-o-toluidine. It can also be obtained by acylation first, followed by chlorination and hydrolysis. Mix the o-toluidine and chlorobenzene with stirring, add dropwise acetic anhydride, stir and react at 70-80°C for 1.5h, cool, and pass chlorine at about 50°C. At this time, a large amount of white solid is suddenly formed. Stop the chlorine flow, add concentrated hydrochloric acid and water, stir and reflux for 2h at 95°C. Cool to room temperature and neutralize it with lye. The yield is more than 70%. Another method is to react o-toluidine hydrochloride with a mixed gas of hydrogen chloride and oxygen (or chlorine and oxygen) in an acid medium.

Uses

Used as pesticide and pharmaceutical intermediate

Production

(1972) GREATER THAN 4.54X10+5 GRAMS|(1975) GREATER THAN 4.54X10+5 GRAMS

PARA-CHLORO-ORTHO-TOLUIDINE IS AVAILABLE IN THE US AS A TECHNICAL GRADE WITH A MIN PURITY OF 99%...

Benzenamine, 4-chloro-2-methyl-: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.

RESIDUES OF CHLORPHENAMIDINE IN PLANT & SOIL MATERIAL WERE DETERMINED BY COLORIMETRY & THIN-LAYER & ELECTRON CAPTURE GC. 4-CHLORO-O-TOLUIDINE WAS HYDROLYSIS PRODUCT OF CHLORPHENAMIDE.|Air: GC/MS (limit of detection not reported) & HPLC/UV (3 ug/sample); plants & soil: colorimetric (0.02-0.05 ppm); soil: GC/FID & GC/MS (limits of detection not reported); rice: GC/FID (0.02 ppm) /from table/

Solid waste: GC/MS (limit of detection 1 ppm); urine & faeces: HPLC (5 ng/ml); urine: TLC (6 ng/ml) & HPLC/UV (0.2 mg/l) /from table/

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:141.60
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:141.0345270
Monoisotopic Mass:141.0345270
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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