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Home > Encyclopedia > 2,4,6-Trimethylaniline

2,4,6-Trimethylaniline

2,4,6-Trimethylaniline structure

2,4,6-Trimethylaniline 

structure
  • CAS No:

    88-05-1

  • Formula:

    C9H13N

  • Chemical Name:

    2,4,6-Trimethylaniline

  • Synonyms:

    Benzenamine,2,4,6-trimethyl-;Aniline,2,4,6-trimethyl-;2,4,6-Trimethylbenzenamine;Aminomesitylene;Mesidine;Mesitylamine;Mesitylene,2-amino-;2,4,6-Trimethylaniline;2-Aminomesitylene;Mesidin;2,4,6-Trimethylphenylamine;1-Amino-2,4,6-trimethylbenzene;NSC 31

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

clear yellow to brown liquid Aniline, 2,4,6-Trimethyl-is a clear liquid.


Aniline, 2,4,6-trimethyl- appears as a liquid. (EPA, 1998)


Aniline, 2,4,6-trimethyl- appears as a liquid. (EPA, 1998)|2,4,6-Trimethylaniline is a substituted aniline.

2,4,6-Trimethylaniline Basic Attributes

135.206

135.21

201-794-3

YIR5CRL5BG

2810

DTXSID5043847

Liquid

2921430090

Characteristics

26.02000

2.3

Aniline, 2,4,6-trimethyl- appears as a liquid. (EPA, 1998)

96 g/cm3

-5 °C

232-234 °C

96.1±0.0 °C

1.553

IMMISCIBLE

Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.

pKa= 4.38

No rapid reaction with air. No rapid reaction with water.

Amines, Aromatic

ANILINE, 2,4,6-TRIMETHYL- 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

III

6.1

UN 2810 6.1/PG 2

3

R23/24/25;R33

S26-S28-S36/37-S45-S28A

BZ0700000

T:Toxic;

P260-P280-P284-P305 + P351 + P338-P310

H302 + H312-H315-H319-H330

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.

Small amounts of aromatic amines - aniline ignite on contact, while larger amounts exploded dangerously, probably owing to rapid formation of diazonium perchlorates.

When heated to decomposition, it emits toxic fumes of nitrogen oxides. Avoid decomposing heat. (EPA, 1998)

|Danger|H301 (44.21%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P284, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 129 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P271, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P314, P320, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

(Non-Specific -- Poisonous Liquid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. If water pollution occurs, notify appropriate authorities. (Non-Specific -- Poisonous Liquid, n.o.s.) Small fires: dry chemical, carbon dioxide, water spray or foam. Large fires: water spray, fog or foam. Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. (EPA, 1998)

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)

(Non-Specific -- Poisonous Liquid, n.o.s.) Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal. Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

A skin and severe eye irritant.

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Aniline, 2,4,6-trimethyl- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Toxicity

LD50 Rat oral 743 mg/kg|LD50 Mouse oral 590 mg/kg|LC50 Mouse ihl 290 mg/cu m/2 hr

2,4,6-Trimethylaniline's production and use in the manufacture 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 2,4,6-trimethylaniline is expected to have moderate mobility in soil(SRC). However, aromatic amines (including anilines) bind to humate 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 4.38(4) suggests that 2,4,6-trimethylaniline will partially exist in the protonated form in moist soils and the protonated form of 2,4,6-trimethylaniline is expected to bind strongly to soil surfaces. Volatilization of 2,4,6-trimethylaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.7X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2,4,6-Trimethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.067 mm Hg(SRC), determined from a fragment constant method(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 198(SRC), determined from an estimation method(2), indicates that 2,4,6-trimethylaniline is expected to slightly adsorb to sediment and suspended solids in water(SRC). In a biodegradation study of 2,4,6-trimethylaniline in a mixed domestic/industrial treatment plant, 0-9% degraded at a concentration of 20 mg/l after 6 hours and 25 °C(3). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 2.7X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 11 and 120 days, respectively(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humate material in the water column(6). However, aromatic amines (including anilines) bind to humate found in water in two phases(6). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humate carbonyls(6). Subsequently, there is a slow reaction that is not readily reversed(6). A pKa of 4.38(7) suggests that 2,4,6-trimethylaniline will partially exist in the protonated form in the aqueous environments and the protonated form of 2,4,6-trimethylaniline is not expected to volatilize from water. According to a classification scheme(8), an estimated BCF of 25(SRC), from an estimated log Kow of 2.72(9) and a regression-derived equation(10), 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), 2,4,6-trimethylaniline, which has an estimated vapor pressure of 0.067 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4,6-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 6.7 hrs(SRC), calculated from its rate constant of 5.7X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 2,4,6-trimethylaniline with photochemically-produced hydroxyl radicals has been estimated as 5.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.7 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,4,6-Trimethylaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

An estimated BCF of 25 was calculated for 2,4,6-trimethylaniline(SRC), using an estimated log Kow of 2.72(1,SRC) 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 2,4,6-trimethylaniline can be estimated to be 198(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,4,6-trimethylaniline is expected to have moderate mobility in soil. However, primary amines(including anilines) bind to humate 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).

The Henry's Law constant for 2,4,6-trimethylaniline is estimated as 2.7X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4,6-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 11 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 120 days(SRC). However, aromatic amines (including anilines) bind to humate found in water 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). A pKa of 4.38(4) suggests that 2,4,6-trimethylaniline will partially exist in the protonated form in the aqueous environments and the protonated form of 2,4,6-trimethylaniline is not expected to volatilize from water. 2,4,6-Trimethylaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,4,6-Trimethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.067 mm Hg(SRC), determined from a fragment constant method(5).

Occupational exposure to 2,4,6-trimethylaniline may occur through inhalation and dermal contact with this compound at workplaces(1) where 2,4,6-trimethylaniline is produced or used(SRC).

Drug Information

This material is moderately toxic orally. It is also considered highly toxic by unspecified routes. It is a skin and eye irritant. Suspect occupational carcinogen. (Non-Specific -- Aromatic Amines) The danger of acute poisoning is represented by methemoglobinemia leading to adverse effects on the red cells. A number of the amines may act as skin sensitizers. (EPA, 1998)

Signs and Symptoms of Aniline, 2,4,6-Trimethyl- Exposure: Acute exposure to aniline, 2,4,6-trimethyl- may result in eye and skin irritation and cyanosis. Headache, nausea, dizziness, and weakness may also occur. Repeated exposure to aniline, 2,4,6- trimethyl- may cause a decrease in the peripheral vision and photosensitivity of the eye. Emergency Life-Support Procedures: Acute exposure to aniline, 2,4,6-trimethyl- may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to aniline, 2,4,6-trimethyl-. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to aniline, 2,4,6-trimethyl-. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Remove and isolate contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 2. DO NOT induce vomiting or attempt to neutralize! 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)

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/

...WORKERS WHO HAD BEEN ENGAGED FOR ELEVEN TO TWENTY YR IN MFR OF MESIDINE & ANILINE WERE REPORTED TO HAVE NARROWING OR PERIPHERAL VISUAL FIELDS, INCR IN SIZE OF BLIND SPOT, & DECR IN "PHOTOSENSITIVITY," FOR WHICH MESIDINE WAS THOUGHT TO BE RESPONSIBLE.

2,4,6-trimethylaniline

2,4,6-Trimethylaniline Use and Manufacturing

Methods of Manufacturing

Produced by reduction of 1,3,5-trimethyl-2-nitrobenzene, which is obtained by nitration of mesitylene under special conditions.

Uses

Dyes

Acid Blue 80, Acid Blue 129

Benzenamine, 2,4,6-trimethyl-: ACTIVE

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:99.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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