m-Toluidine
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m-Toluidine
structure -
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CAS No:
108-44-1
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Formula:
C7H9N
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Chemical Name:
m-Toluidine
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Synonyms:
Benzenamine,3-methyl-;m-Toluidine;3-Methylbenzenamine;3-Aminotoluene;3-Methylaniline;m-Aminotoluene;3-Toluidine;3-Aminophenylmethane;1-Amino-3-methylbenzene;m-Tolylamine;3-Methylphenylamine;(m-Methylphenyl)amine;m-Methylaniline;NSC 15349
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CAS No:
Description
Colorless liquid. Slightly soluble in water; soluble in alcohol or ether. Combustible.A clear colorless liquid. Flash point below 200°F. Vapors heavier than air. Toxic by inhalation, ingestion, and skin absorption in high concentrations or under prolonged exposures. Used in the manufacture of organic chemicals. Density about 8 lb / gal.
M-toluidine appears as a clear colorless liquid. Flash point below 200°F. Vapors heavier than air. Toxic by inhalation, ingestion, and skin absorption in high concentrations or under prolonged exposures. Used in the manufacture of organic chemicals. Density about 8 lb / gal.|Liquid|COLOURLESS-TO-YELLOW LIQUID. TURNS DARK ON EXPOSURE TO AIR AND LIGHT.|Colorless to light-yellow liquid with an aromatic, amine-like odor.|Colorless to light-yellow liquid with an aromatic, amine-like odor. [Note: Used as a basis for many dyes.]
M-toluidine appears as a clear colorless liquid. Flash point below 200°F. Vapors heavier than air. Toxic by inhalation, ingestion, and skin absorption in high concentrations or under prolonged exposures. Used in the manufacture of organic chemicals. Density about 8 lb / gal.
m-Toluidine Basic Attributes
107.15
107.15
635944
203-583-1
006FKQ96T3
0342
15349
1708
DTXSID1026792
Colorless to light yellow liquid
29171990
Characteristics
26
1.40
White Crystalline Solid or Liquid
0.9889 g/cm3 @ Temp: 20 °C
-31.2 °C
203.3 °C
186 °F
n 20/D 1.567(lit.)
H2O: 0.2 g/100 mL (20 ºC)
Refrigerator
Vapour pressure, Pa at 25°C: 17
Relative vapour density (air = 1): 3.7
Oral-rat LD50: 450 mg/kg; Oral-Mouse LD50: 740 mg/kg
Combustible in case of open flame; burning produces toxic nitrogen oxide fumes; reacts with oxidants
vol% in air: 1.1.6
Aromatic, amine-like odor
1.66e-06 atm-m3/mole|Henry's Law constant = 1.66X10-6 atm-cu m/mol at 25 °C
pKa = 4.69 at 25 °C (conjugate acid)
Heat of formation: -8.1 kJ/mol|Combustible|Hydroxyl radical reaction rate constant = 2.0X10-10 cu cm/molec-sec at 25 °C (est)
Slightly soluble in water.
Amines, Aromatic
M-TOLUIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. Can react vigorously with oxidizing reagents. Emits toxic fumes of oxides of nitrogen when heated to decomposition [Lewis, 3rd ed., 1993, p. 1253].
899 °F (USCG, 1999)|481 °C (898 °F)|480 °C
7.50 eV
Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.
As a result of flow, agitation, etc., electrostatic charges can be generated.
44.9 kJ/mol at 203.3 °C
Critical temperature = 709 K; critical pressure = 4.2 Mpa
Safety Information
II
6.1
UN 1708 6.1/PG 2
2
45-23/24/25-33-50
53-28-36/37-45-61-28A
XU2800000
T,N
The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives
Toxic
Stable under normal temperatures and pressures.
P261-P273-P280-P301 + P310-P305 + P351 + P338-P311
H301 + H311 + H331-H319-H373-H410
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Toluidine is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices). /Toluidine/|The following wastewater treatment technologies have been investigated for m-aminotoluene: concentration process: biological treatment.
Can react vigorously on contact with oxidizing materials.|Aromatic amines (e.g., aniline or toluidine) in triethylamine solution are ignited rapidly by red fuming nitric acid at a temperature of minus 76 °C or lower. /Toluidine, nitric acid plus aniline/|Oxidizers, acids.|Addition of potassium iodide solution to diazotised 3-toluidine was accompanied on 3 occasions by an erruption of the beaker content.
Organization for Economic Cooperation and Development; Screening Information Data Set for m-Toluidine (108-44-1) (September 2000). This OECD Initial Assessment of HPV Chemicals is part of a series of OECD SIDS documents published by UNEP Chemicals to facilitate the access to information needed for health and environmental risk assessments of chemicals.[Available from, as of April 30, 2010: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html]|European Commission, ESIS; IUCLID Dataset, m-Toluidine (108-44-1) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of April 30, 2010: http://esis.jrc.ec.europa.eu/]
UN 1708
Special Hazards of Combustion Products: Toxic oxides of nitrogen and flammable vapors may form in fire. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 85 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H301+H311+H331 (16.45%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P314, P321, P322, P330, P337+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 231 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P307+P311, P308+P313, P314, P321, P330, P332+P313, P337+P313, P362, P370+P378, P391, P403+P235, P405, and P501|P201, P202, P210, P260, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P235, P405, and P501
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)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|(See protection codes)
Flammable when exposed to heat or flame.
Lower explosive limit: 1.1% by volume; Upper explosive limit: 6.6% by volume|Above 86 °C explosive vapor/air mixtures may be formed.|Explosive limits , vol% in air: 1.1-6.6
To fight fire, use foam, carbon dioxide, dry chemical.|If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Toluidines, liquid or solid/|Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Toluidines, liquid or solid/
Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Toluidines, liquid or solid/|Personnel protection: Avoid breathing vapors. Keep upwind. /Toluidines, liquid or solid/|The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|For more Preventive Measures (Complete) data for 3-Aminotoluene (8 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. /Toluidines; Toluidines, liquid; Toluidines, 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. /Toluidines; Toluidines, liquid; Toluidines, 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. /Toluidines; Toluidines, liquid; Toluidines, 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. /Toluidines; Toluidines, liquid; Toluidines, solid/|For more DOT Emergency Guidelines (Complete) data for 3-Aminotoluene (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.
A skin and eye irritant.
Vacated 1989 OSHA PEL TWA 2 ppm (9 mg/cu m), skin designation, is still enforced in some states.
NIOSH questioned whether the PEL proposed for m-toluidine [TWA 2 ppm (skin)] was adequate to protect workers from recognized health hazards.
Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Provision to contain effluent from fire extinguishing. Separated from strong oxidants, strong acids and food and feedstuffs. Well closed. Ventilation along the floor. Keep in the dark. Store in an area without drain or sewer access.
Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.
The substance is irritating to the eyes. The substance is mildly irritating to the skin. 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.
The substance may have effects on the blood. This may result in the formation of methaemoglobin.
NO open flames. Above 85 °C use a closed system and ventilation.
STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety goggles.
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. Toluidines are produced, as an intermediate or a final product, by process units covered under this subpart. /Toluidines/
| 4 - Materials that, under emergency conditions, can be lethal.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
Toxicity
highly toxic
Human Health. Although the metabolites, 2-amino-4-methylphenol and 4-amino-2-methylphenol were identified in the rat urine with a small amount of the parent compound, there is not sufficient information on metabolism and toxicokinetics. Acute toxicity of m-toluidine is low because the oral LD50 values in rat, mouse and rabbit are from 450 to 1,430 mg/kg. This chemical is slightly irritating to skin and moderately irritating to eyes. There is no information available on skin sensitization. In accordance with an OECD combined repeat dose and reproductive/developmental toxicity screening test [TG 422], m-toluidine was given to Crj: CD (SD) male and female rats by gavage at doses of 0, 30, 100, 300 mg/kg/day for at least 41 days. The critical effect at 100 and 300 mg/kg is a hemolytic anemia, revealed by reduction of erythrocyte counts and hemoglobin concentration, and histological changes such as pigment deposit and extramedullary hematopoiesis in liver and spleen. Other toxicity is renal tubular epithelium lesions accompanied with pigment deposit in kidney. As there is suggestive evidence of hemolytic anemia such as marginal pigment deposit and extramedullary hematopoiesis in spleen at the lowest dose of 30 mg/kg, probably caused by methemoglobin formation, LOAEL for repeat dose toxicity was 30 mg/kg/day. In the above screening test [OECD TG 422], m-toluidine was given from 14 days before mating to 14 days after mating in males and from 14 days before mating to day 3 of lactation in females. As implantation losses were found in all animals at 300 mg/kg and two of ten at 100 mg/kg but not at 30 mg/kg, NOAEL for reproductive toxicity is 30 mg/kg/day. The death of all pups or more than half the number of pups observed at 30 and 100 mg/kg/day is considered as the result of maternal toxicity because there is clear evidence of the lack of the nursing activity, probably due to anemia, and all live offsprings of 30 and 100 mg/kg had normally developed up to 4 days. Therefore the NOAEL for developmental toxicity is considered to be 100 mg/kg/day. Bacterial genotoxicity studies show negative results in S. typhimurium and E. coli with and without metabolic activation. In chromosomal aberration test conducted in cultured Chinese hamster lung (CHL/IU) cells by OECD TG 473, clastogenicity was not observed but significant increase of polyploidy (0.9 to 1.25 %) was found at the highest concentration. However, this result was considered not to be positive because it was within historical control and generally accepted criteria of significance (5 %). Two kinds of in vivo studies, sister chromatid exchange and inhibition of DNA-synthesis, also show negative results. Therefore m-toluidine is considered not to be genotoxic. Tumors were not observed in dietary study of male rats at 9,400 ppm and male and female mice at 14,700 and 20,400 ppm, respectively. However, the carcinogenicity in rodents is inconclusive because the experimental conditions were insufficient compared to a current carcinogenicity testing protocol. Environment. This chemical is mainly persistent in water and it will be transported to water compartment when released to other environmental compartments. The chemical is not readily biodegradable, and its bioaccumulation potential is low. This chemical has been tested in a limited number of aquatic species. For algae, 72 hr EC50 (biomass change in Selenastrum capricornutum) is 17.7 mg/L. For Daphnia, the lowest acute toxicity value is 0.73 mg/L (48 hr EC50 for immobilization), and the lowest chronic value is 0.01 mg/L (21d NOEC for reproduction). For fish, only acute data were available, the lowest of which is 34 mg/L (96 hr LC50, Oryzias latipes). PNEC of 0.0001 mg/L for the aquatic organisms was calculated from the lowest chronic value (NOEC for Daphnia; 0.01 mg/L) using an assessment factor of 100. Toxicity of this chemical to aquatic organisms, specially against Daphnia, is high. Exposure. The production volume of m-toluidine in Japan was less than 100 tonnes in 1990 - 1992, and imported volume was 97-285 tonnes/year in 1988-1992, however both the production volume and imported volume in Japan in 1998 was 0 ton. This chemical is used as intermediates for pigments, photography agents and others. This chemical is stable in neutral or alkaline solutions, and is classified as "not readily biodegradable". Direct photodegradation is expected. The half-life is estimated to be about 4 months. A generic fugacity model (Mackey level III) shows this chemical would be distributed mainly to water. In the monitoring study of the general environment in Japan in 1977, m-toluidine was detected from surface water and sediment, but in the monitoring study in 1999, it was not detected in water, sediment or air. According to a Japanese manufacturer, 400 kg/year (estimated) of m-toluidine are released with 1 x 10+7 tonnes/year of effluent into bay. Local predicted environmental concentration (PEClocal) is 4.0 x 10-5 mg/L, employing the calculation model. The highest exposure to the general population via the environment would be expected through drinking water processed from surface water. The concentration in drinking water is assumed to be less than 4.0 x 10-5 mg/L. Consumer exposure is negligible because m-toluidine is not contained in consumer products. As m-toluidine is mainly produced in a closed system, occupational exposures at production sites may occur by the inhalation and dermal route. Estimated human exposure for a worker who operates sampling (0.1 hr/day), drum filling (1.5 hr/day), and reaction vessel cleaning (2 day/year) without protective equipment is less than 0.21 mg/kg/day. By wearing chemical cartridge respirator during these operations, and ventilation systems during the filling process, exposure level is lower than the estimation.
LD50 Rat oral 450 mg/kg|LD50 Rat oral 974 mg/kg|LD50 Rat oral 1160 mg/kg|LD50 Rat oral 1430 mg/kg|For more Non-Human Toxicity Values (Complete) data for 3-Aminotoluene (12 total), please visit the HSDB record page.
3-Aminotoluene's production and use in the manufacture of photographic agents(1), various dyes and other organic chemicals(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an average Koc value of 44 measured in four silt loam soils(2), indicates that 3-aminotoluene is expected to have very high mobility in soil(SRC). The pKa of 3-aminotoluene is 4.69(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of 3-aminotoluene from moist soil surfaces is expected to be an important fate process for the neutral species(SRC) given a Henry's Law constant of 1.66X10-6 atm-cu m/mole(5). 3-Aminotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.303 mm Hg at 25 °C(6). Complete degradation of 3-aminotoluene was obtained within 8 days with a soil inoculum(7), suggesting that 3-aminotoluene will be readily biodegradable in the terrestrial environment. Additionally, aromatic amines undergo soil- and clay-catalyzed free radical oxidations(8,9). They are also readily oxidized by metal ions that may occur in soil(10).|AQUATIC FATE: Based on a classification scheme(1), an average Koc value of 44 measured in four silt loam soils(2), indicates that 3-aminotoluene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is expected(3) based upon a Henry's Law constant of 1.66X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 23 and 170 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3.9(SRC), from a log Kow of 1.40(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 3-Aminotoluene reached 50% of its theoretical BOD in 5 days using water inoculum(8) and 97.7% degradation occurred in 5 days using activated sludge inoculum(9), suggesting that 3-aminotoluene will be readily biodegradable in the aquatic environment. Additionally, aromatic amines are readily oxidized by metal ions that may occur in natural waters(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-aminotoluene, which has a vapor pressure of 0.303 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-aminotoluene 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 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3-Aminotoluene has a UV absorption band at 286 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 3-aminotoluene with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3-Aminotoluene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 3-Aminotoluene has a UV absorption band at 286 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC). Colored degradation products are formed in the presence of light and oxygen with the reaction rate being first order with respect to oxygen and proportional to the intensity of irradiation(3). Photochemical half-lives of approximately 5.1 and 68 hours were measured for irradiation with a germicidal UV lamp and a fluorochemical lamp operating at 300-400 nm, respectively(4). Aromatic amines are sensitive to oxidation by air and undergo soil- and clay-catalyzed free radical oxidation(5,6). They are also readily oxidized by metal ions that may occur in soil or natural waters(5). In four hours, 13-27% of aminotoluene (isomer unspecified) was oxidized after being mixed with 20 ppm of ferric ion(7).
An estimated BCF of 3.9 was calculated for 3-aminotoluene(SRC), using a log Kow of 1.40(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
33.88 L/kg|The mean Koc of 3-aminotoluene in 4 silt loam soils was 44 over a pH range of 6.1 to 7.5(1). According to a classification scheme(2), this Koc value suggests that 3-aminotoluene is expected to have very high mobility in soil. The pKa of 3-aminotoluene is 4.69(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility of the neutral species may be much lower in some soils(SRC).
The Henry's Law constant for 3-aminotoluene is 1.66X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that the neutral species of 3-aminotoluene 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 23 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 170 days(SRC). 3-Aminotoluene's Henry's Law constant indicates that volatilization of the neutral species from moist soil surfaces may occur(SRC). 3-Aminotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.303 mm Hg(3).
GROUNDWATER: 3-Aminotoluene was found in a shallow aquifer 205 m from the site of a former coal-tar distillation plant in St. Louis Park, MN at a concn of 297 ppb(1). It was found in 2 of 3 samples of groundwater at the site of the Hoe Creek coal gasification project in northeastern WY, 15 mo after gasification was completed, but not in a nearby control well (detection limit 0.5 ppb)(2). The concn of 3-aminotoluene in these wells ranged from 1.5-3.3 ppb(2).
In a German survey of primary and secondary amines in the human environment, no 3-aminotoluene was reported in samples of preserved vegetables, maize, salad, rhubarb, and apples, pickles, fish, cheese, bread, coffee, tea, cocoa, wine, malt, hops, barley, or animal feed(1).
According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 3-aminotoluene is 1000 or greater; the data may be greatly underestimated(1).|Occupational exposure to 3-aminotoluene may occur through dermal contact with this compound at workplaces where 3-aminotoluene is produced or used. Use data indicate that the general population may be exposed to 3-aminotoluene via dermal contact with this compound or other products containing 3-aminotoluene. (SRC)
Drug Information
After a single oral administration of 500 mg m-toluidine to rats (strain not given), only 2.5% of the unchanged compound was recovered from the urine for 24 hrs and two metabolites, 2-amino-4-methylphenol and 4-amino-2-methylphenol were identified after hydrolysis of the urine extract. However, there is no information on the quantitative metabolism and excretion. After dermal application to rats, m-toluidine was dose-dependently detected in the blood. In the case of a single iv injection of 111.1 mg m-toluidine-HCl/kg bw to dogs, the metabolite, m-nitrosotoluene in blood reached to a maximum concentration of 3.5 ug/mL at 30 min and still remained at approx. 1 ug/mL at 5 hrs.|m-Toluidine was detected in the blood plasma of rats after dermal application (tail). The plasma levels correlated with the dose-level.|... Absorbed by skin.|Absorbed via respiratory tract.|Urinary levels in rats of o-, m-, and p-toluidine (20, 100, or 200 mg/kg, intragastric administration) were positively correlated with the toluidine dose; 26, 10, and 10% of the unchanged toluidines, respectively, were excreted after 24 hr. After chronic administration of m-toluidine, excretion rate of the unchanged toluidine increased with duration of the experiment.
Two metabolites, 2-amino-4-methylphenol and 4-amino-2-methylphenol, were identified after hydrolysis of the urine extract /from rats (strain not given)/..|The binding of monocyclic aromatic amines to hemoglobin was studied in vivo. Female Wistar rats were administered aniline, N-methylaniline, N,N-dimethylaniline, o-toluidine, m-toluidine, p-toluidine, 2,4-dimethylaniline, 2,4,5-trimethylaniline, p-chloroaniline 3,4-dichloroaniline, 4-chloro-o-toluidine, 5-chloro-o-toluidine, or 6-chloro-o-toluidine by gavage. Blood samples were collected 24 hr later and the hemoglobin was isolated. The hemoglobin samples were extracted with hexane, hydrolyzed with sodium hydroxide, and the amount of each amine recovered was determined by gas chromatography. The extent of amine/hemoglobin binding was determined by computing hemoglobin binding indices (HBIs) from the administered doses and the amount of amine recovered. Female B6C3F1 mice were administered aniline, o-toluidine, p-chloroaniline, 4-chloro-o-toluidine, or 5-chloro-o-toluidine. The extent of amine/hemoglobin binding was determined as before. Rats were given 2,4-dimethylaniline, aniline, 5-chloro-o-toluidine, 4-aminobiphenyl, or p-chloroaniline, and the extent of methemoglobin formation was determined. In rats hydrolysis of the hemoglobin yielded only one cleavage product, the parent amine, in each case. An additional signal was seen in the chromatogram in the case of 6-chloro-o-toluidine. The hemoglobin binding indices ranged from 0.7 for 2,4,5-trimethylaniline to 569 for p-chloroaniline. The binding of aniline, o-toluidine, p-chloroaniline, 4-chloro-o-toluidine, and 5-chloro-o-toluidine in mice was significantly lower than in rats. The extent of amine/hemoglobin binding in rats correlated well with the maximum concentrations of methemoglobin. /Results indicate/ that determining hemoglobin adducts may be useful for monitoring occupational exposure to amines.|30 min after a single intravenous administration of 0.77 mmol (= 111.1 mg) m-toluidine-HCl/kg bw to dogs, a maximum concentration of 3.5 ug m-nitrosotoluene/mL blood was reached. 5 hours after the injection the concentration of m-nitrosotoluene was still about 1 ug/mL blood. /m-Toluidine hydrochloride/|In vitro, the p-hydroxylation of m-toluidine by rabbit liver microsomes was measured with a specific activity of 0.43 nmol/min and mg microsomal protein.|For more Metabolism/Metabolites (Complete) data for 3-Aminotoluene (8 total), please visit the HSDB record page.
Absorption of toxic quantities by any route causes cyanosis (blue discoloroation of lips, nails, skin); nausea, vomiting, and coma may follow. Repeated inhalation of low concentrations may cause pallor, low-grade secondary anemia, fatigability, and loss of appetite. Contact with eyes causes irritation. (USCG, 1999)
Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)
Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.
Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.
Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. 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. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/
/HUMAN EXPOSURE STUDIES/ An exposure of 40 ppm (176 mg/cu m) in atmosphere for 60 min produced severe intoxication in persons.|/SIGNS AND SYMPTOMS/ Inhalation: Blue lips or finger nails. Blue skin. Dizziness. Headache. Laboured breathing. Shortness of breath. Weakness. Skin: May be absorbed. Redness. Blue lips or fingernails. Blue skin. Eyes: Redness. Pain. Ingestion: Blue lips or fingernails. Blue skin. Dizziness. Headache. Labored breathing ... The substance may have effects on the blood, resulting in formation of methemoglobin.|/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/|/EPIDEMIOLOGY STUDIES/ Epidemiological aspects of aromatic amine cancers are discussed. Industrial exposure to aromatic amines has been linked with occupational bladder cancer since the end of the last century. Aromatic amines of industrial importance such as 1-naphthylamine, 1-naphthylthiourea, benzidine, 4-biphenylamine, 4,4'-methylenedianiline, 3,3'-dichlorobenzidine, diphenylamine, toluidine, o-toluidine, and p-toluidine are discussed. The epidemiology of bladder cancer is reviewed. Data for the United States in 1981 showes age adjusted incidence rates of bladder cancer per 100,000 of the male population ranging from 7.5 in Puerto Rico to 17.1 in Connecticut. It is noted that the incidence of bladder cancer has been increasing. The epidemiology of industrial bladder cancer is discussed. The historical development of bladder cancer epidemiology is summarized. Studies in the United Kingdom have indicated that 2-naphthylamine is the major carcinogenic amine in the British dyestuffs industry. ... Screening as a means of protecting workers at risk is discussed.|For more Human Toxicity Excerpts (Complete) data for 3-Aminotoluene (11 total), please visit the HSDB record page.
3-aminotoluene
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact
irritation eyes, skin; dermatitis; hematuria (blood in the urine), methemoglobinemia; cyanosis, nausea, vomiting, low blood pressure, convulsions; anemia, lassitude (weakness, exhaustion)
Blue lips, fingernails and skin. Confusion. Dizziness. Headache. Shortness of breath. Weakness. Convulsions. Nausea. Unconsciousness.
Redness. Further see Inhalation.
Redness. Pain.
Eyes, skin, blood, cardiovascular system
m-Toluidine Use and Manufacturing
By reduction of m-nitrotoluene with iron powder.
Dyes, manufacture of organic chemicals. m-Toluidine is an intermediate in the manu facture of dyes and other chemicals.
Intermediates
25,000 - 100,000 lb|(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS|Benzenamine, 3-methyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3813]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzenamine, 3-methyl-. Aggregated National Production Volume: 500,000 to < 1 million pounds.
All other basic organic chemical manufacturing|Benzenamine, 3-methyl-: ACTIVE
Method: OSHA 73; Procedure: gas chromatography using an electron capture detector; Analyte: m-toluidine; Matrix: air; Detection Limit: 0.18 ppb (0.79 ug/cu m).|GAS CHROMATOGRAPHIC ANALYSIS OF AROMATIC AMINES AS N-PERMETHYLATED DERIVATIVES. /AROMATIC AMINES/|GAS CHROMATOGRAPHIC DETERMINATION OF TOLUIDINE ISOMERS IN THE AIR OF INDUSTRIAL INSTALLATIONS. /TOLUIDINE ISOMERS/
Fire Hazards -> Flammable - 2nd degree|Environmental transformation -> Pesticide transformation products (metabolite, successor)
3-aminotoluene is a known environmental transformation product of phenmedipham.|M-toluidine is a known environmental transformation product of Phenmedipham.
Analysis Methods
| Name | Column Shape | Active Phase(℃) | Retention index | Temperature Control | Method | Comments | Reference |
|---|---|---|---|---|---|---|---|
| Kovats' RI, non-polar column, isothermal | Packed | SE-30 | 1088. | 180. | isothermal | N2, Chromosorb A AW; Column length: 3. m | Oszczapowicz, J.Osek, J.Ciszkowski, K.Krawczyk, W.Ostrowski, M.Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar ColumnJ. Chromatogr.1985, 330, 79-85. |
| Kovats' RI, non-polar column, isothermal | Packed | SE-30 | 1088. | 180. | isothermal | N2, Chromosorb W AW; Column length: 3. m | Oszczapowicz, J.Osek, J.Dolecka, E.Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar columnJ. Chromatogr.1984, 315, 95-100. |
| Kovats' RI, non-polar column, isothermal | Packed | Carbowax 20M | 1840.0 | 150. | isothermal | Chromosorb W, AW-DMCS | Ellis, T.S.Still, R.H.Thermal degradation of polymers. XXI. Vacuum pyrolysis of poly(m-N,N-dimethylaminostyrene); the products volatile at pyrolysis temperature, liquid at room temperatureJ. Appl. Polym. Sci.1979, 23, 10, 2837-2854. |
| Kovats' RI, non-polar column, isothermal | Packed | PEG-2000 | 1835. | 179. | isothermal | He, Celite 545 (44-60 mesh); Column length: 3. m | Anderson, A.Jurel, S.Shymanska, M.Golender, L.Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phasesLatv. PSR Zinat. Akad. Vestis Kim. Ser.1973, 1, 51-63. |
| Kovats' RI, non-polar column, isothermal | Packed | PEG-2000 | 1840. | 180. | isothermal | He, Celite 545 (44-60 mesh); Column length: 3. m | Anderson, A.Jurel, S.Shymanska, M.Golender, L.Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phasesLatv. PSR Zinat. Akad. Vestis Kim. Ser.1973, 1, 51-63. |
Computed Properties
Molecular Weight:107.15
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:107.073499291
Monoisotopic Mass:107.073499291
Topological Polar Surface Area:26
Heavy Atom Count:8
Complexity:70.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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