2,4,6-トリメチルアニリン

2,4,6-Trimethylaniline

HCID 6913CAS 88-05-1

基本情報

標準SMILES
Cc1cc(C)c(N)c(C)c1
InChIKey
KWVPRPSXBZNOHS-UHFFFAOYSA-N
分子式
C9H13N
平均分子量
135.21 g/mol
単同位体質量
135.10479942

名称と識別子

優先名称
2,4,6-Trimethylaniline
IUPAC
2,4,6-trimethylaniline
現地名
2,4,6-トリメチルアニリン
英語名
2,4,6-Trimethylaniline
分子式
C9H13N
分子量
135.21

名称と別名

2,4,6-TRIMETHYLANILINE88-05-1MesidineAminomesityleneMesitylamineBenzenamine, 2,4,6-trimethyl-2-Aminomesitylene2,4,6-TrimethylbenzenamineMesidin2-Amino-1,3,5-trimethylbenzeneAniline, 2,4,6-trimethyl-Mesitylene, 2-amino-
名称をさらに表示
2,4,6-トリメチルアニリン2,4,6-トリメチルベンゼン-1-アミン2-アミノメシチレンアミノメシチレン2-アミノ-1,3,5-トリメチルベンゼンメシジン2,4,6-トリメチルベンゼンアミンメシチルアミン2,4,6トリメチルアニリン2,4,6‐トリメチルアニリン2,4,6-TrimethylanilinehydrochlorideMezidineMESIDENEIsotritoluidine
2,4,6-TrimethylphenylamineYIR5CRL5BG1-Amino-2,4,6-trimethylbenzen1-Amino-2,4,6-trimethylbenzeneNSC-31DTXSID5043847RefChem:82142DTXCID3023847

データベース識別子

CAS
88-05-1
PubChem CID
6913
DTXSID
DTXSID5043847
ChEBI
CHEBI:82545
UNII
YIR5CRL5BG
EC Number
201-794-3
Nikkaji
J4.286B

物性

構造計算による物性

XLogP
2.3
極性表面積
26 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
10

実験および物理化学的性質

Density · 3 件

0.9633 (EPA, 1998) - Less dense than water; will float

0.96 kg/l

0.96 @25 °C

Color/FormLiquid
SolubilityInsoluble in water
Boiling Point · 3 件

450 to 451 °F at 760 mmHg (EPA, 1998)

232-234 °C

232 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits toxic fumes of nitroxides.
Melting Point · 3 件

23 °F (EPA, 1998)

-5 °C

-5 °C

物理化学的性質

融点
-5 °C · -5 °C
沸点
108 · 108-110 °C11 mm Hg(lit.)
比重(密度)
0.963 g/mL · 0.963 g/mL at 25 °C(lit.)
屈折率
20 · n20/D 1.551(lit.)
闪点
205 °F · 205 °F
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature

化学的性質

化学的特性clear yellow to brown liquid. Insoluble in water, soluble in organic solvents such as ethanol and ether.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 36.9% (38 of 103) of reports.

Danger

H301 (10.7%): Toxic if swallowed [Danger Acute toxicity, oral];H302 (52.4%): Harmful if swallowed [Warning Acute toxicity, oral];H311 (12.6%): Toxic in contact with skin [Danger Acute toxicity, dermal];H312 (48.5%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (57.3%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (59.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H330 (51.5%): Fatal if inhaled [Danger Acute toxicity, inhalation];H335 (16.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H373 (12.6%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 103 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 38 of 103 reports by companies.;There are 15 notifications provided by 65 of 103 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 4 件

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

Status: Active Update: 24-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22322

2,4,6-Trimethylaniline: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits toxic fumes of nitrogen oxides. Avoid decomposing heat. (EPA, 1998)
Health Hazards · 1 件

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)

Hazards Summary · 1 件

Irritating to skin; Severely irritating to eyes; Oral LD50 (rat) = 743 mg/kg; Causes liver injury in high-dose animal experiments; [HSDB] An irritant; Effects in high-dose animal studies include lacrimation, toxic hepatitis, and methemoglobinemia; [MSDSonline] See 2,4,5-Trimethylaniline.

Reactive GroupAmines, Aromatic

安全と保護具

Fire Fighting · 1 件

(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)

First Aid · 1 件

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.

Nonfire Spill Response · 1 件

(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)

Disposal Methods · 1 件

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.

Preventive Measures · 1 件

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.

Isolation and Evacuation · 1 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:;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 the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank 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, 2024)

毒性情報

Environmental Fate · 3 件

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).

Adverse Effects · 1 件

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Soil Adsorption/Mobility · 1 件

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).

Human Toxicity Excerpts · 1 件

...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.

Artificial Pollution Sources2,4,6-Trimethylaniline's production and use in the manufacture of dyes(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

AEROBIC: In a pure culture study using Escherichia coli B, 2,4,6-trimethylaniline was not found to degrade after 7 days incubation at 37 °C in total darkness(1). 2,4,6-Trimethylaniline exhibited 0-9% depletion at 20 mg/l after 6 hrs @ 25 °C in a mixed domestic/industrial treatment plant(2).

法規制情報

Regulatory Information · 4 件

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

Status: Active Update: 24-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22322

2,4,6-Trimethylaniline: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

CERCLA Reportable Quantities · 1 件

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.

安全データ

wgk
3
tsca
TSCA listed
rtecs
BZ0700000
ridadr
UN 2810 6.1/PG 2
hs_code
29214980
risk_code
21/22-26-36/38-33-23/24/25

化学と産業

用途と製造

Uses · 2 件

Used in dyes; [HSDB]

Dyes

Methods of ManufacturingProduced by reduction of 1,3,5-trimethyl-2-nitrobenzene, which is obtained by nitration of mesitylene under special conditions.
Formulations/PreparationsAcid Blue 80, Acid Blue 129
General Manufacturing InformationBenzenamine, 2,4,6-trimethyl-: ACTIVE
応用分野 · 3 件

用途染料、顔料、その他有機工業薬品中間体。

使用2,4,6-Trimethylaniline is useful for the preparation of Grubbs' catalyst. It is used as a precursor to dyes. It undergoes condensation reaction with glyoxal to prepare glyoxal-bis(mesitylimine). It is also involved in the preparation of 1,3-diketimines ligands by condensation with 1,3-diketones. Further, it is used for the production of Acid Blue 129 dye, which is useful in histochemistry studies. In addition to this, it serves as a building block to various bulky ligands.

一般的な説明2,4,6-Trimethylaniline is a clear liquid. easily turns light brown when exposed to air and light. It is an intermediate for dyes, organic pigments and pesticides.

調製方法 · 1 件

製造方法2,4,6-Trimethylaniline is prepared by selective mononitration of mesitylene, avoiding oxidation of the methyl groups.Mix sulfuric acid and nitric acid into mixed acid, nitrify with mesitylene at atmospheric pressure below 10°C for 4 hours, stand for stratification, and let off the waste acid. The obtained 2,4,6-trimethylnitrobenzene, iron powder, hydrochloric acid and water were prepared in a ratio of 1:3.74:0.9:2.22 (mol ratio) for reduction reaction at 100-105°C for 8h. Crude 2,4,6-Trimethylaniline was then distilled off from the reduced material and purified by distillation.

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