Mesitylene

HCID 7947CAS 108-67-8

基本情報

標準SMILES
Cc1cc(C)cc(C)c1
InChIKey
AUHZEENZYGFFBQ-UHFFFAOYSA-N
分子式
C9H12
平均分子量
120.19 g/mol
単同位体質量
120.09390038

概要

1,3,5-trimethylbenzene appears as a colorless liquid with a peculiar odor. Insoluble in water and less dense than water. Flash point near 123 °F. May be toxic by ingestion and inhalation. Used to make plastics and dyes.

名称と識別子

優先名称
Mesitylene
IUPAC
1,3,5-trimethylbenzene
現地名
メシチレン
英語名
Mesitylene
分子式
C9H12
分子量
120.19

名称と別名

MESITYLENE1,3,5-Trimethylbenzene108-67-8sym-Trimethylbenzene3,5-DimethyltolueneFleet-XTrimethylbenzolBenzene, 1,3,5-trimethyl-DTXSID6026797887L18KQ6XNSC-9273DTXCID506797
名称をさらに表示
1,3,5-トリメチルベンゼン1,3,5-トリメチルベンゼン (1mg/mlメタノール溶液) [水質分析用]syn-トリメチルベンゼンsym-トリメチルベンゼン2,4,6-トリメチルベンゼン1,3,5トリメチルベンゼン1,3,5-トリメチルベンゼン(メシチレン)1,3,5-トリメチルベンゼン (MESITYLメシチレンSOOCTANE (1000ΜG/ML)1,3,5-トリメチルベンゼン STANDARD1,3,5-トリメチルベンゼン (MESITYLメシチレンYCLOHEXANE (30MG/ML)水分分析用標準液(0.1 MG/G)メシチレン, 98+%1,3,5-トリメチルベンゼン 溶液1,3,5‐トリメチルベンゼン1,3,5-トリメチルベンゼン Standard, 0.2 mg/mL in MeOH1,3,5-トリメチルベンゼン Standard, 5.0 mg/mL in MeOH1,3,5-トリメチルベンゼン, 2.0 mg/mL in MeOHメシチレン1,3,5-トリメチルベンゼン(脱水) -Super-メシチレン(脱水) -Super-1,3,5-trimethylbenzene (mesitylene)1.3.5-TriMethy1,3,5-Trimethylbenze1,3,5-trimethyl-benzen1,3,5-Trimethylbenzene Standard
CHEBI:34833Symmetrical trimethylbenzeneRefChem:6006203-604-4s-Trimethylbenzene2,4,6-trimethylbenzene1,3,5-trimethyl-benzeneNSC 9273

データベース識別子

CAS
108-67-8
PubChem CID
7947
DTXSID
DTXSID6026797
ChEMBL
CHEMBL1797281
ChEBI
CHEBI:34833
UNII
887L18KQ6X
EC Number
203-604-4
Nikkaji
J2.424D

物性

構造計算による物性

XLogP
3.4
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
9

実験および物理化学的性質

Chemical ClassesVolatile Organic Compound (VOC)
SolventsSolvents -> Aromatic Solvents
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (Benzene, 1,3,5-trimethyl-) -> IFRA transparency List
PesticidesPesticide -> EPA IRIS
LogP · 4 件

log Kow = 3.42

3.42

3.42

3.84

物理化学的性質

融点
-45 °C · -45 °C
沸点
163 · 163-166 °C(lit.)
比重(密度)
0.864 g/mL · 0.864 g/mL at 25 °C(lit.)
蒸気密度
4.1 · 4.1 (vs air)
蒸気圧
14 mm · 14 mm Hg ( 55 °C)
屈折率
20 · n20/D 1.499(lit.)

化学的性質

化学的特性Mesitylene is a clear, colorless liquid. Distinctive, aromatic odor.

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P319, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 2655) of reports.

Danger

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

危険有害性情報

Regulatory Information · 5 件

Chemical: Benzene, 1,3,5-trimethyl-

Hazard Traits - Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity

Benzene, 1,3,5-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,3,5-trimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 17-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/9977

Benzene, 1,3,5-trimethyl-: HSNO Approval: HSR001229 Approved with controls

DOT LabelFlammable Liquid
Fire Hazards · 3 件

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 50 °C explosive vapour/air mixtures may be formed.

Fire PotentialMODERATE, VIA HEAT, FLAMES, OXIDIZERS
Health Hazards · 2 件

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· May cause toxic effects if inhaled or absorbed through skin.

Hazards Summary · 1 件

A skin, eye, nose, throat and respiratory tract irritant; [Merck Index] A skin, eye, and respiratory tract irritant; Defats the skin; May have effects on the central nervous system and blood; [ICSC] A skin, eye, and respiratory tract irritant; [HSDB] A nose, throat, and lung irritant; Inhalation of high concentrations can cause CNS depression; [CHEMINFO] A respiratory tract irritant; [eChemPortal: ESIS] See Trimethyl benzene isomers.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Use alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 件

Excerpt from NIOSH Pocket Guide for 1,3,5-Trimethylbenzene:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants. Well closed. Keep in a well-ventilated room.
Exposure Control and Personal Protection · 2 件

· Wear positive pressure self-contained breathing apparatus (SCBA).

20.0 [ppm]

毒性情報

Body Burden · 1 件

5 of 46 human adipose tissue samples contained unreported concentrations of 1,3,5-trimethylbenzene(1). Expired air from 28 humans contained 1,3,5-trimethylbenzene at an average concn of 4 ng/L(2). Expired air from 54 humans contained 1,3,5-trimethylbenzene at an average concn of 0.842 ng/L(3). Expired air from 3 of 8 male humans contained 1,3,5-trimethylbenzene at 0.034 to 0.81 ug/hr; the source was thought to be of metabolic origin(4).

Interactions · 2 件

Increased catalase activity was observed in the liver microsomal fraction of ethanol-treated rats (10% v/v aqueous ethanol solution per os for 5 weeks). In contrast, cytochrome P-450 concentration and specific activity of NADPH-cytochrome c reductase remained at the same level as in the liver of control rats (drinking water). ... Administration of mesitylene (1,3,5-trimethylbenzene) by gastric tube for 3 days (5 mmoles per kg daily) increased cytochrome P-450 concentration, specific activity of NADPH-cytochrome c reductase and ethanol metabolism.

Groups of 5 female SPF Sprague-Dawley rats (200 to 220 g) were exposed via inhalation for 2 hr to 120, 180, 400, or 720 ppm mesitylene, without or in combination with 1000 or 4000 ppm ethyl acetate. Immediately after exposure, blood samples were collected. Co-exposure /of the effect/ with ethyl acetate ... was not statistically significant. For example, at 400 ppm mesitylene, control blood concn was (75.8 +/- 2.1) x 10-6 mol/L vs 68.8 +/ - 7.8) x 10-6 mol/L at 4000 ppm ethyl acetate.

Target Organs · 2 件

Developmental

Eyes, skin, respiratory system, central nervous system, blood

Ecotoxicity Values · 5 件

EC50 Daphnia magna /(Water flea)/ 50 mg/L 24 hr, toxic effect: increased mortality and reduced reproduction rates

EC50; Species: Scenedesmus subspicatus (Green algae, Log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 25000 ug/L for 48 hr; Effect: decreased population biomass

EC50; Species: Scenedesmus subspicatus (Green algae, Log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 53000 ug/L for 48 hr; Effect: general population changes

EC50; Species: Daphnia magna (Water flea, age 4-6 days, length 1.5 mm); Conditions: freshwater, static, 23 °C, pH 6-7, dissolved oxygen 5-9 mg/L; Concentration: 50 mmol/cu m for 48 hr (95% confidence interval: 22-110 mmol/cu m); Effect: intoxication, immobilization /> or = 97% purity/

For more Ecotoxicity Values (Complete) data for 1,3,5-TRIMETHYLBENZENE (9 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc range of 501-1,445(2-5), indicates that 1,3,5-trimethylbenzene is expected to have low mobility in soil(SRC). Volatilization of 1,3,5-trimethylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given an experimental Henry's Law constant of 8.77X10-3 atm-cu m/mole(6). 1,3,5-Trimethylbenzene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.48 mm Hg(SRC), from experimentally-derived coefficients(7). Complete removal of 1,3,5-trimethylbenzene from sterile sandy loam soil samples contaminated with jet fuel was reported within 5 days, probably due to evaporation(8). Biodegradation is expected to occur in soil, and acclimation may increase the rate of biodegradation(SRC). 1,3,5-Trimethylbenzene, present at a concn of 50 mg/kg, degraded considerably after 6 months in the presence of a sewage inoculum during a bioremediation study(9). It was noted that 1,3,5-trimethylbenzene was more resistant to biodegradation than other compounds present(9). The time required for 0.2-1.0 mg/L of 1,3,5-trimethylbenzene to reach less than 1 ug/L was 110 hours in an adapted groundwater aquifer contaminated with gasoline(10).

AQUATIC FATE: Based on a classification scheme(1), an experimental Koc range of 501-1,445(2-5), indicates that 1,3,5-trimethylbenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected based upon a Henry's Law constant of 8.77X10-3 atm-cu m/mole(6). Using this Henry's Law constant and an estimation method(7), volatilization half-lives for a model river and model lake are 1.2 hours and 4.4 days, respectively(SRC). Residence times (with respect to volatilization) for 1,3,5-trimethylbenzene were calculated as 220 hours for both winter and summer conditions in Narragansett Bay(8). According to a classification scheme(9), BCF values of 23 to 342(10), measured in carp, suggest that bioconcentration in aquatic organisms may be high(SRC). Biodegradation may be an important fate process for this compound in water, and acclimation may increase the rate of biodegradation(SRC). The time required for 0.2-1.0 mg/L of 1,3,5-trimethylbenzene to reach less than 1 ug/L was 110 hours in an adapted groundwater aquifer contaminated with gasoline(11). 1,3,5-Trimethylbenzene was not detected in the effluent of an activated sludge plant that had a recorded influent of 22.7 ug/L(12). In liquid wastewater cultures, after 30 days 1,3,5-trimethylbenzene degraded to 0.39 mg/L in the test sample compared to 7.17 mg/L residual concn in the abiotic control, suggesting biodegradation is an important fate process in water(13).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3,5-trimethylbenzene, which has a vapor pressure of 2.48 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3,5-trimethylbenzene 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 11 hours(SRC), calculated from its rate constant of 5.75X10-11 cu cm/molecule-sec at 25 °C(1). 1,3,5-Trimethylbenzene also reacts with nitrate radicals in the atmosphere(3); the half-life for this reaction in air is estimated as 10-67 days(SRC). The photooxidation of 1,3,5-trimethylbenzene with nitrogen oxide produces formaldehyde and aliphatic aldehydes at 0.15-0.2 and 0.3-0.4 moles/mole 1,3,5-trimethylbenzene, respectively(5). 1,3,5-Trimethylbenzene does not contain chromophores that absorb wavelengths >290 nm(6) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1 件

An aroma concentrate of cured beef contained 1,3,5-trimethylbenzene at 0.11 mg/kg(1). 1,3,5-Trimethylbenzene was reported as a component of fried beef liver (4.34-5.57 ppb)(2), margarine (13.1 ppb)(2), butter (7.81 ppb)(2), cake doughnuts (27.6 ppb)(2), sandwich cookies (7.25 ppb)(2), in scrambled eggs from both fresh and supermarket eggs (trace levels)(3), and chickpea seed(4). 1,3,5-Trimethylbenzene is a volatile component of chicken, beef, and pork flavors(5).

法規制情報

TSCA Requirements · 2 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3,5-Trimethylbenzene is included on this list. Effective date: 2/13/1984; Sunset date: 2/13/1994.

A testing consent order is in effect for 1,3,5-trimethylbenzene for health effects testing. FR citation: FR 59681 11/10/1993.

State Drinking Water Guidelines · 5 件

(CA) CALIFORNIA 330 ug/l

(CT) CONNECTICUT 36 ug/l

(FL) FLORIDA 35 ug/l

(MN) MINNESOTA 100 ug/L

(NH) NEW HAMPSHIRE 330 ug/L

安全データ

F
10
OEB
A
OEL
TWA: 25 ppm (125 mg/m3)
wgk
2
tsca
TSCA listed
rtecs
OX6825000

化学と産業

薬理情報

Biological Half-Life · 1 件

... Ten healthy male volunteers were exposed to trimethylbenzene (TMB) vapor in an exposure chamber for 2 hr at a work load of 50 W. The subjects were exposed on four occasions, to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, respectively, and 2 ppm of 1,2,4-TMB. Urine was collected from the onset of exposure until the following morning. All six possible dimethylhippuric acid (DMHA) isomers were analyzed by high-performance liquid chromatography. ... The half-times of the different DMHA isomers ranged from 4 to 16 hr.

Metabolism/Metabolites · 5 件

... Only a small portion is excreted unchanged by the lungs, the greater part is oxidized to water-soluble metabolites, which are excreted by the urine, partly free, partly conjugated /as/ glycine and mesitylenic acid.

Mesitylene yields 2,4,6-trimethylphenol in rat. /from table/

Approximately 78% of oral dose of mesitylene was excreted as 3,5-dimethylhippuric acid; additional 7.6 and 8.2% were excreted as glucuronic and sulfuric acid conjugates.

Toxicity of Tri- and Tetramethylbenzenes: Material: 1,3,5-trimethylbenzene; Route of entry: oral (subacute); Species: rat; Dose or concentration: 1.2 g/kg/day; Results or Effects: Metabolites: 3,5-dimethylhippuric acid 78.0%, 3,5-dimethylbenzoic glucuronide 7.6%, and 3,5-dimethylbenzoic sulfate 1.2%. /From table/

The possibility of evaluating occupational exposure to mesitylene /depending/ on the determination of unchanged solvent in capillary blood or 3,5-dimethylbenzoic acid in urine was investigated. The volunteers were exposed to mesitylene in a toxicological chamber (range 10-150 mg/cu m). Concn of the solvent or its metabolite in biological material were determined by gas chromatography. The toxicokinetic data concerning retention in the lung, absorption and elimination of mesitylene and its metabolite in biological fluids were obtained. The highest correlation coefficient value was obtained for the relationship between the absorbed dose of mesitylene and the excretion rate of 3,5-dimethylbenzoic acid in urine (r= 0.95). ...

Absorption, Distribution and Excretion · 4 件

The objective of this study was to determine the uptake and disposition of inhaled trimethylbenzenes (TMBs) in man. The toxicokinetics were studied in 10 male, healthy volunteers exposed to TMB vapor in an exposure chamber for 2 hr during a work load of 50 W. The subjects were exposed on four occasions to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, and to 2 ppm of 1,2,4-TMB. The TMB isomers were analyzed in blood, urine, and exhaled air by gas chromatography. The relative respiratory uptake was in the range 56-64%. The elimination of TMBs was moderate compared to other aromatic solvents, with a total blood clearance of 0.6-1.0 L per hr per kg. Large volumes of distribution (30-39 liters/kg) and long terminal half-lives of the TMBs in blood (78-120 hr) imply extensive accumulation in adipose tissue. Exhalation during and postexposure accounted for 20-37% of the absorbed amount, whereas the urinary excretion of unchanged TMBs was low (< or = 0.002%). The kinetics of 1,2,4-TMB seemed linear up to 25 ppm. ...

Absorption takes place most readily by inhalation of the vapor, but the liquid can be absorbed from the gastro-intestinal tract, and probably, though slowly, by the intact skin.

... Only a small portion is excreted unchanged by the lungs, the greater part is oxidized to water-soluble metabolites, which are excreted by the urine, partly free, partly conjugated /as/ glycine and mesitylenic acid.

... Ten healthy male volunteers were exposed to trimethylbenzene (TMB) vapor in an exposure chamber for 2 hr at a work load of 50 W. The subjects were exposed on four occasions, to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, respectively, and 2 ppm of 1,2,4-TMB. Urine was collected from the onset of exposure until the following morning. All six possible dimethylhippuric acid (DMHA) isomers were analyzed by high-performance liquid chromatography. About 22% of the inhaled amount of 1,2,4-TMB was excreted as DMHAs within 24 hr, mainly as 3,4-DMHA. The 24-hr recovery of 1,2,3-TMB as DMHAs was 11%. Only 3% of the absorbed amount of 1,3,5-TMB was excreted as 3,5,-DMHA. ... In addition to analysis of DMHAs, the excretion of unconjugated dimethylbenzoic acids in urine was estimated to account for approximately 3% of the dose of all TMBs. In conclusion, the urinary excretion of DMHA isomers may serve as a good indicator of TMB exposure. In this controlled short-term-exposure study the sum of excretion rate of several DMHA isomers reflected exposure more closely than did the excretion rate of any single DMHA.

Cellular LocationsMembrane

用途と製造

Uses · 6 件

Found in coal tar and petroleum crudes; [Merck Index] Used to make dyes and UV oxidation stabilizers for plastics; Also used as a solvent and paint thinner; [HSDB]

Painting (Solvents) [Category: Paint]

DYESTUFF INTERMEDIATE, SOLVENT, PAINT THINNER

Chem int for anthraquinone vat dyes and for uv oxidation stabilizers for plastics

Used as a chemical intermediate for the synthesis of mesidine; trimesic acid; 2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)mesitylene.

The principal use for mesitylene is its conversion to 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; trade name is Ethanox 330 ... an important non-coloring stabilizer (antioxidant) for plastics, adhesives, rubber, and waxes.

ImpuritiesMesitylene contains 1 wt% pseuodocumeme and 0.5 wt% other aromatic compounds
U.S. Imports · 3 件

(1972) No Data

(1975) No Data

(1984) 1.58X10+8 g

U.S. Production · 6 件

2023: 850,000 - <1,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1986) No Data

1,3,5-Trimethylbenzene 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#269]

Consumer UsesSolvent
Industry UsesFuel agents
応用分野 · 5 件

解説メシチレン,液体.融点-44.8 ℃,沸点165 ℃.d204 0.8611.n25D 1.4968.アルコール類やエーテルとまざる.溶剤として,あるいは染料,顔料,医薬品などの合成原料として用いられる.森北出版「化学辞典(第2版)

用途染料、顔料、薬、抗酸化剤中間体

使用Mesitylene is used to make plastics and dyes. It acts as a solvent, ligand in organometallic chemistry and precursor to 2,4,6-trimethylaniline. It is also used as a developer for photopatternable silicones due to its solvent properties in the electronics industry. It is used as an internal standard in nuclear magnetic resonance (NMR) samples due to the presence of three equivalent protons in it. It is involved in the production of trimesic acid and antioxygen, epoxy firming agent and polyester resin stabilizers. Further, it is used as an additive and component in aviation gasoline blends.

一般的な説明A colorless liquid with a peculiar odor. Insoluble in water and less dense than water. Flash point near 123°F. May be toxic by ingestion and inhalation. Used to make plastics and dyes.

使用用途メシチレンとしては、その有機化合物への溶解性の高さから、有機合成における高沸点溶媒として広く用いられています。また、その溶解度の高さを活かしエレクトロニクスの分野では、半導体ウェハーの写像形成におけるとして用いられています。 さらに、染料、顔料、医薬品などの合成原料として用いられています。

調製方法 · 1 件

純化方法Dry it with CaCl2 and distil it from Na in a glass helices-packed column. Treat it with silica gel and redistil it. Alternative purifications include vapour-phase chromatography, or fractional distillation followed by azeotropic distillation with 2-methoxyethanol (which is subsequently washed out with H2O), drying and fractional distilling. More exhaustive purification uses sulfonation by dissolving in two volumes of conc H2SO4, precipitating with four volumes of conc HCl at 0o, washing with conc HCl and recrystallising from CHCl3. The mesitylene sulfonic acid is hydrolysed with boiling 20% HCl and steam distilled. The separated mesitylene is dried (MgSO4 or CaSO4) and distilled. It can also be fractionally crystallised from the melt at low temperatures. [Beilstein 5 IV 1016.]

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補足説明

定義ChEBI: A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.

関連反応

321 件

関連ノート

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