2,4,5-Trimethylaniline
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2,4,5-Trimethylaniline
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CAS No:
137-17-7
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Formula:
C9H13N
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Chemical Name:
2,4,5-Trimethylaniline
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Synonyms:
Benzenamine,2,4,5-trimethyl-;Aniline,2,4,5-trimethyl-;2,4,5-Trimethylbenzenamine;2,4,5-Trimethylaniline;Pseudocumidine;ψ-Cumidine;2,4,5-Trimethylphenylamine;NSC 37004;NSC 5297
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CAS No:
Description
white to light tan crystalline solidWhite crystals or beige powder.
2,4,5-trimethylaniline appears as white crystals or beige powder. (NTP, 1992)
2,4,5-trimethylaniline appears as white crystals or beige powder. (NTP, 1992)|2,4,5-Trimethylaniline is a substituted aniline.
2,4,5-Trimethylaniline Basic Attributes
135.21
135.21
205-282-0
00KUO98F97
37004|5297
DTXSID9021398
White crystals|NEEDLES OBTAINED FROM WATER AS SOLVENT
2921430090
Characteristics
26
2.27
2,4,5-trimethylaniline appears as white crystals or beige powder. (NTP, 1992)
0.957 g/cm3
68 °C
234.5 °C
-5 °C
1.5130 (estimate)
Sol in alcohol and ether; insol in water
2-8°C
1 mm Hg at 155.1° F ; 10 mm Hg at 228.2° F (NTP, 1992)
2.48e-06 atm-m3/mole|Henry's Law constant= 2.48X10-6 atm-cu m/mol @ 25 °C
pKa= 5.09
Insoluble in water.
Amines, Aromatic
2,4,5-TRIMETHYLANILINE 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. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Safety Information
UN16483/PG2
2
11-20/21/22-36-51/53-23/24/25-45
16-36/37-61-45-53
BZ0520000
F,Xn,N,T
Harmful
Stable. Combustible. Incompatible with strong oxidizing agents.
P210-P280-P305 + P351 + P338
H225-H302 + H312 + H332-H319
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.
DHEW/NCI; Bioassay of 2,4,5-Trimethylaniline for Possible Carcinogenicity (1979) Technical Rpt Series No. 160 DHEW Pub No. (NIH) 79-1716
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
|Danger|H301 (97.67%): 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 43 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 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 store this material under ambient temperatures. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxicity
LD50 Rat oral 1250 mg/kg
A bioassay of 2,4,5-trimethylaniline for possible carcinogenicity was conducted by admin the test chemical in feed to F344 rats and B6C3F1 mice. Groups of 50 rats and 50 mice of each sex were admin 2,4,5-trimethylaniline at one of two doses, either 200 or 800 ppm for the rats and either 50 or 100 ppm for the mice, for 101 wk. Matched controls consisted of 20 untreated rats and 20 untreated mice of each sex. All surviving animals were /sacrificed/ at the end of admin of the test chemical. It is concluded that under the conditions of this bioassay, 2,4,5-trimethylaniline was carcinogenic for male and female F344 rats and female B6C3F1 mice, inducing hepatocellular carcinomas or neoplastic nodules in the rats of each sex, alveolar/bronchiolar carcinomas in the female rats, and hepatocellular carcinomas in female mice. ... Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice: Equivocal; Female Mice: Positive.
2,4,5-Trimethylaniline's production and use in the production of dyes(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 198(SRC), determined from a structure estimation method(2), indicates that 2,4,5-trimethylaniline is expected to have moderate mobility in soil(SRC). However, aromatic amines (including anilines) bind to humic material found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humate carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). Also, a pKa value of 5.09(4) suggests that 2,4,5-trimethylaniline will partially exist in the protonated form in moist soils and the protonated form of 2,4,5-trimethylaniline is expected to bind strongly to soil surfaces. Volatilization of the neutral species from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.48X10-6 atm-cu m/mole(4). 2,4,5-Trimethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.0X10-3 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 198(SRC), determined from an estimation method(2), indicates that 2,4,5-trimethylaniline is expected to adsorb very little to sediment and suspended solids in water(SRC). Volatilization of the neutral species from water surfaces is expected(3) based upon a Henry's Law constant of 2.48X10-6 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 12 and 129 days, respectively(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(4). Aromatic amines (including anilines) bind to humic material found in water in two phases(4). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humate carbonyls(4). Subsequently, there is a slow reaction that is not readily reversed(4). A pKa value of 5.09(5), suggests that 2,4,5-trimethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of 2,4,5-trimethylaniline does not volatilize from water. According to a classification scheme(6), an estimated BCF of 11(SRC), from a log Kow of 2.27(5) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,5-trimethylaniline, which has a vapor pressure of 9.0X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4,5-trimethylaniline 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 2 hrs(SRC), from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3).
The rate constant for the vapor-phase reaction of 2,4,5-trimethylaniline 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 2 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,4,5-Trimethylaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). In general, anilines absorb light in the environmental UV spectrum(>290 nm)(3). Based on this, 2,4,5-trimethylaniline is expected to absorb light and may potentially undergo direct photolysis(SRC).
An estimated BCF of 11 was calculated for 2,4,5-trimethylaniline(SRC), using a log Kow of 2.27(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.
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,4,5-trimethylaniline can be estimated to be 198(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,4,5-trimethylaniline is expected to have moderate mobility in soil. However, aromatic amines(including anilines) bind to humic material found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). Also, a pKa value of 5.09(4) suggests that 2,4,5-trimethylaniline will exist partially in the protonated form in moist soils and the protonated form of 2,4,5-trimethylaniline is expected to bind strongly to soil surfaces(SRC).
The Henry's Law constant for 2,4,5-trimethylaniline is 2.48X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that the neutral species of 2,4,5-trimethylaniline 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 12 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 129 days(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(3). Aromatic amines (including anilines) bind to humic material found in water in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). 2,4,5-Trimethylanilne's Henry's Law constant(1) indicates that volatilization of the neutral species from moist soil surfaces may occur(SRC). A pKa value of 5.09(1), suggests that 2,4,5-trimethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of 2,4,5-trimethylaniline does not volatilize from water or moist soil surfaces(SRC). 2,4,5-Trimethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.0X10-3 mm Hg(1).
Occupational exposure to 2,4,5-trimethylaniline may occur through inhalation and dermal contact with this compound at workplaces where 2,4,5-trimethylaniline is produced or used in the production of dyes(1,SRC).
Drug Information
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (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. 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)
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/
SYMPTOMATOLOGY: 1. GRAYISH BLUE CYANOSIS, WITHOUT SIGNS OF CARDIAC OR PULMONARY INSUFFICIENCY. 2. SEVERE HEADACHE, NAUSEA, SOMETIMES VOMITING, DRYNESS OF THROAT. 3. CNS SYMPTOMS: CONFUSION, ATAXIA, VERTIGO, TINNITUS, WEAKNESS, DISORIENTATION, LETHARGY, DROWSINESS, & FINALLY COMA. CONVULSIONS...UNCOMMON. /ANILINE/|SYMPTOMATOLOGY: 4. CARDIAC EFFECTS: HEART BLOCKS, ARRHYTHMIAS, & SHOCK. 5. DEATH, ALTHOUGH UNCOMMON, IS USUALLY DUE TO CARDIOVASCULAR COLLAPSE & NOT RESPIRATORY PARALYSIS. 6. URINARY SIGNS & SYMPTOMS...PAINFUL MICTURITION, HEMATURIA, HEMOGLOBINURIA (& METHEMOGLOBINURIA), OLIGURIA, & RENAL INSUFFICIENCY... /ANILINE/|MODERATELY TOXIC.
2,4,5-TMA
2,4,5-Trimethylaniline Use and Manufacturing
PROBABLY BY NITRATION OF PSEUDOCUMENE FOLLOWED BY REDUCTION
Manufacture of dyes, organic synthesis.
(1972) NOT PRODUCED COMMERCIALLY IN US|(1975) NOT PRODUCED COMMERCIALLY IN US
OSW Method 8270B. Determination Semivolatile Organic compounds by Gas Chromatography/Mass Spectrometry (GC/MS): Capillary Column Technique.|EPA Method EAD 1625. Semivolatile Organic Compounds by Isotope Dilution GCMS.
Computed Properties
Molecular Weight:135.21
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:135.104799419
Monoisotopic Mass:135.104799419
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:111
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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