1,2,3-Trimethylbenzene

HCID 10686CAS 25551-13-7

基本情報

標準SMILES
Cc1cccc(C)c1C
InChIKey
FYGHSUNMUKGBRK-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

1,2,3-trimethylbenzene is a trimethylbenzene carrying methyl groups at positions 1, 2 and 3. It has been found in Centaurium erythraea. It has a role as a neurotoxin and a plant metabolite.

名称と識別子

優先名称
1,2,3-Trimethylbenzene
IUPAC
1,2,3-trimethylbenzene
現地名
トリメチルベンゼン(unspecified isomers)
英語名
trimethylbenzene
分子式
C9H12
分子量
120.19

名称と別名

1,2,3-TRIMETHYLBENZENE526-73-8HemimelliteneHemellitolHemimellitolZK4R7UPH6RNSC-5167DTXCID7027750CHEBI:34037RefChem:53594208-394-8Trimethylbenzene
名称をさらに表示
トリメチルベンゼントリメチルベンゼン(unspecified isomers)methylxylenerimethylbenzeneTRIMETHYLBENZENEStrimethyl-benzenAqualyte(TM), LSC cocktailTrimethylbenzene solvent oilTRIMETHYLBENZENE(MIXEDISOMERS)Trimethylbenzenes, all isomers or mixtures
Benzene, 1,2,3-trimethyl-25551-13-7DTXSID8047769MFCD000085201,2,3-trimethyl-benzeneBenzene, trimethyl-1,3-TrimethylbenzeneHemimellitene, 90.5%

データベース識別子

CAS
25551-13-7、526-73-8
PubChem CID
10686
DTXSID
DTXSID8047769
ChEMBL
CHEMBL1797279
ChEBI
CHEBI:34037
UNII
ZK4R7UPH6R
EC Number
208-394-8、247-099-9
Nikkaji
J1.582B

物性

構造計算による物性

XLogP
3.6
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
PesticidesPesticide -> EPA IRIS
LogP · 3 件

log Kow = 3.66

3.7

3.78

OdorDistinctive, aromatic odor

物理化学的性質

融点
-68.52 °C · -68.52°C (estimate)
沸点
159.22 °C · 159.22°C (estimate)
比重(密度)
0.8803 · 0.8803 (estimate)
屈折率
1.5 · 1.5000 (estimate)
外見
無色の液体
EPAの化学物質情報
Trimethylbenzene (25551-13-7)

化学的性質

化学的特性Liquid. Insoluble in water.

化学性质トリメチルベンゼンはベンゼン環に三つのメチル基を持つ芳香族炭化水素である。

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 2.5% (42 of 1654) of reports.

Warning

H226 (95%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1654 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 1.8% (28 of 1532) of reports.

危険有害性情報

Regulatory Information · 4 件

Chemical: Benzene, 1,2,3-trimethyl-

Hazard Traits - Neurotoxicity

Benzene, 1,2,3-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,2,3-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)

1,2,3-Trimethylbenzene: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsFlammable. Above 44 °C explosive vapour/air mixtures may be formed.
Fire PotentialThis chemical is a flammable liquid.
Hazards SummaryA skin, eye, and respiratory tract irritant; [ICSC] A mild irritant; Inhalation of high concentrations can cause CNS depression; [CHEMINFO] See Trimethyl benzene isomers.
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
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. Trimethylbenzene (mixed isomers) is included on this list. Effective date 2/13/1984; Sunset date 2/13/1994.

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. 1,2,3-Trimethylbenzene is included on this list. Effective date: 2/13/1984; Sunset date: 11/9/1993.

安全と保護具

Fire FightingUse alcohol-resistant foam, foam, 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.

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 .

First Aid(General first aid procedures)
Safe StorageFireproof. Well closed. Separated from oxidants.
Exposure Control and Personal Protection20.0 [ppm]
Fire Fighting Procedures · 2 件

This chemical is a flammable liquid. Poisonous gases are produced in fire. Small fires: dry chemical, carbon dioxide, water spray, or alcohol-resistant foam. Large fires: water spray, fog, or alcohol foam. Move container from fire if you can do so without risk. Spray cooling water on containers that are exposed to flames until well after fire is out. For massive fire in cargo area, use unmanned hose holder or monitoring nozzles; if this is impossible, withdraw from area and let fire burn. Isolate for one-half mile in all directions if tank car or truck is involved in fire. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.

This chemical is a flammable liquid. Poisonous gases are produced in fire. Small fires: dry chemical, carbon dioxide, water spray, or alcohol-resistant foam. Large fires: water spray, fog, or alcohol foam. Move container from fire if you can do so without risk. Spray cooling water on containers that are exposed to flames until well after fire is out. For massive fire in cargo area, use unmanned hose holder or monitoring nozzles; if this is impossible, withdraw from area and let fire burn. Isolate for one-half mile in all directions if tank car or truck is involved in fire. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156. /Trimethyl benzenes/

毒性情報

Target Organs · 2 件

Hematologic

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

Ecotoxicity Values · 3 件

LC50; Species: Palaemonetes pugio (Daggerblade grass shrimp); Conditions: saltwater, static, 21 °C, pH 8.1, salinity 15 parts per thousand, dissolved oxygen >5.0 mg/L; Concentration: 7000 ug/L for 24 hr

LC50; Species: Palaemonetes pugio (Daggerblade grass shrimp); Conditions: saltwater, static, 21 °C, pH 8.1, salinity 15 parts per thousand, dissolved oxygen >5.0 mg/L; Concentration: 5600 ug/L for 48 hr

LC50; Species: Palaemonetes pugio (Daggerblade grass shrimp); Conditions: saltwater, static, 21 °C, pH 8.1, salinity 15 parts per thousand, dissolved oxygen >5.0 mg/L; Concentration: 5400 ug/L for 96 hr

Environmental Fate · 6 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), a Koc range of 501 to 1,445 measured in soil(2-9), suggests that trimethylbenzenes will have low mobility in soil(SRC). Volatilization of trimethylbenzenes from moist soil surfaces may be important(SRC) based on Henry's Law constants of 4.36X10-3 to 8.77 atm-cu m/mole(10). Volatilization from dry soil surfaces is expected(SRC), based on a vapor pressure range of 1.69 to 2.48 mm Hg(11). Screening studies indicate that trimethylbenzenes are slow to degrade and are not classified as readily biodegradable under aerobic conditions(12,13).

AQUATIC FATE: Based on a recommended classification scheme(1), a Koc range of 501-1,445 measured in soil(2-9), indicates that trimethylbenzenes are expected to adsorb to sediment and particulate matter in the water column(SRC). Trimethylbenzenes are expected to volatilize from water surfaces(10) based on Henry's Law constants of 4.36X10-3 to 8.77 atm-cu m/mole(11). Using these Henry's Law constants and an estimation method(3), volatilization half-lives for a model river and model lake are approximately 3 hours and 4 days, respectively(SRC). According to a classification scheme(12), BCF values of 23-342 measured in fish(13), suggests the potential for bioconcentration in aquatic organisms is moderate to high(SRC). Screening studies indicate that trimethylbenzenes are slow to degrade and are not classified as readily biodegradable under aerobic conditions(13,14).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethylbenzenes, which have a vapor pressure range of 1.69 to 2.48 mm Hg 25 °C(2), will exist solely as vapors in the ambient atmosphere. Vapor-phase trimethylbenzenes are degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and nitrate radicals(SRC). The half-life for the reaction with hydroxyl radicals is estimated to be about 7 to 12 hours calculated from a rate constant ranges of 3.25X10-11 to 5.75X10-11 cu cm/molecule-sec at 25 °C(3). The half-life for the reaction in air with nitrate radicals is estimated as 10-67 days(SRC), calculated from rate constants of 2.4X10-16 and 1.60X10-15 cu cm/molecule-sec at 25 °C(4). Trimethylbenzenes do not contain chromophores that absorb wavelengths >290 nm(5) and therefore are not expected to be susceptible to direct photolysis by sunlight(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 1,096(2) and 630(3) indicate that 1,2,3-trimethylbenzene is expected to have low mobility in soil(SRC). Volatilization of 1,2,3-trimethylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.36X10-3 atm-cu m/mole(4). 1,2,3-Trimethylbenzene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.69 mm Hg(5). Biodegradation of 1,2,3-trimethylbenzene may occur in aerobic environments(6) but is likely to be slow based upon 0% theoretical BOD in the Japanese MITI test(8); it is unlikely to biodegrade in anaerobic environments(7).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 1,096(2) and 630(3) indicate that 1,2,3-trimethylbenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 4.36X10-3 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 3.4 hours and 4.4 days, respectively(SRC). According to a classification scheme(6), a BCF range of 133-259(7) suggests bioconcentration in aquatic organisms is high(SRC). Biodegradation of 1,2,3-trimethylbenzene may occur in oxygenated water(8) but is likely to be slow based upon 0% theoretical BOD in the Japanese MITI test(7); it is unlikely to biodegrade in anaerobic environments(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,3-trimethylbenzene, which has a vapor pressure of 1.69 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2,3-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 12 hours(SRC), calculated from its rate constant of 3.27X10-11 cu cm/molecule-sec at 25 °C(3). 1,2,3-Trimethylbenzene also reacts with ozone and nitrate radicals in the atmosphere; the half-life for these reactions are 20 years(4) and 60 days, respectively(5).

Food Survey Values1,2,3-Trimethylbenzene was found in boiled shrimp and crab meat(1). 1,2,3-Trimethylbenzene was found as a volatile component of chickpea seed(2), beef(3), pork(3), frankfurters(4), and plums(5).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation.

inhalation, ingestion, skin and/or eye contact

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. Trimethylbenzene (mixed isomers) is included on this list. Effective date 2/13/1984; Sunset date 2/13/1994.

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. 1,2,3-Trimethylbenzene is included on this list. Effective date: 2/13/1984; Sunset date: 11/9/1993.

安全データ

OEB
A
OEL
TWA: 25.0 ppm; 125.0 mg/m3
tsca
TSCA listed
ridadr
2325
化審法
3-7;3-3427
hazard_class
3.2

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 · 2 件

The structure was investigated of the mercapturic acid excreted in urine of rats after the i.p. administration of 1,2,3-trimethylbenzene. Of the two regioisomeric mercapturic acids, i.e. N-acetyl-S-(2,3-dimethylbenzyl)-L-cysteine and N-acetyl-S-(2,6-dimethyl-benzyl)-L-cysteine, only the former was isolated by preparative HPLC and identified, by comparison with an authentic specimen. The excretion rate of the mercapturate was estimated to be approximately 5% of dose, not a substantial metabolic route.

Toxicity of Tri- and Tetramethylbenzenes: Material: 1,2,3-trimethylbenzene; Route of entry: oral (subacute); Species: rat; Dose or concentration: 1.2 g/kg; Results or Effects: Metabolites: 2,3-dimethylhippuric acid 17.3%, 2,3-dimethylbenzoic glucuronide 19.4%, and 2,3-dimethylbenzoic sulfate 19.9%. /From table/

Absorption, Distribution and Excretion · 4 件

Trimethylbenzene (TMB) ... is a mixture of three isomers (pseudocumene-1,2,4-TMB; mesitylene-1,3,5-TMB; hemimellitene-1,2,3-TMB). The proportion of individual isomers in the mixture differs. The aim of this study was to obtain toxicokinetic data on the absorption and elimination of trimethylbenzene and its metabolites in biological fluids and to investigate the relationship between the biological indices of exposure and the absorbed dose. Eight-hour inhalation tests were performed in a toxicological chamber, The subjects were eight volunteers aged 20-39 with no history of exposure to TMB. They were exposed to pseudocumene, mesitylene or hemimellitene at concentrations ranging from 5 to 150 mg/cu m air. Exhaled air, capillary blood and urine samples were collected before, during and after the exposure. The determinations of TMB or its metabolites were performed using gas chromatography (HP 5890 II Plus, MSD, FID). Pulmonary ventilation in the volunteers ranged from 0.56 to 1.0 cu m/hr. The retention of 1,2,4-TMB; 1,3,5-TMB; 1,2,3-TMB in the lungs was 68%, 67% and 71%, respectively. The elimination of TMB from capillary blood occurred in accordance with the open three-compartment model. Urinary excretion of dimethylbenzoic acids (DMBA) proceeded according to the open two-compartment model. Based on the toxicokinetic data, a simulation model of accretion and excretion of DMBA in urine during a 14-day period was developed. The highest rates of metabolite excretion and the highest quantities of DMBA in urine during 24-hr intervals were observed on day 5 of exposure. The relationship between the levels of TMB or DMBA in biological material and TMB air concentration or absorbed dose were determined. ...

The objective of this study was to compare the toxicokinetics of inhaled 1,2,4-trimethylbenzene (1,2,4-TMB) in man after exposure to white spirit with that observed after exposure to 1,2,4-TMB alone. ... The toxicokinetics were studied in 9 male, healthy volunteers exposed to solvent vapors in an exposure chamber for 2 hr during a work load of 50 W. The subjects were exposed to 11 mg/cu m of 1,2,4-TMB on two occasions; during exposure to 1,2,4-TMB vapor alone and during exposure to 300 mg/cu m of white spirit. The 1,2,4-TMB isomer was analyzed in blood and exhaled air by gas chromatography. In addition, a major urinary metabolite of 1,2,4-TMB, 3,4-dimethylhippuric acid (3,4-DMHA), was analyzed by high performance liquid chromatography. ... Blood levels of 1,2,4-TMB and excretion rates of 3,4-DMHA in urine were markedly elevated both during and after exposure to white spirit as compared to exposure to TMB alone. Thus, it appears that components in white spirit inhibit the metabolic elimination of 1,2,4-TMB. This should be considered in biological exposure monitoring as well as in risk assessment. No irritation or central nervous system effects were reported at these conditions.

The substance can be absorbed into the body by inhalation.

... 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

Used as a solvent and to make dyes, perfumes, and other organic chemicals; [HSDB] Present in gasoline; [CHEMINFO]

... Used as solvents and in dye and perfume manufacture. ...

Listed as an inert ingredient in pesticide formulations; List 3-Inerts of unknown toxicity.

Raw material for chemical synthesis

... Used as solvents and in dye and perfume manufacture. ... /Trimethyl benzenes/

Hemimellitene is an intermediate in the production of fragrances.

U.S. Production · 3 件

2023: 25,000 - <50,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#6319]

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7254]

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesFuel agents
Methods of Manufacturing · 4 件

Trimethylbenzenes can be produced by Friedel-Crafts methylation of toluene or xylene with chloromethane in the presence of aluminum chloride.

Trimethylbenzenes are also generated in the reaction of toluene with synthesis gas over a dual catalyst consisting of a metal oxide component and an aluminum silicate, at 200-400 °C and up to 20 MPa.

Fusel oils and other fermentation products may be reacted on the zeolite catalyst HZSM-5 to form aromatic compounds, including trimethylbenzenes.

... Hemimellitene ... /is/ found in coal tar oil ... /It/ can be isolated by distillation and purified by the differential hydrolysis of ... /its/ sulfonic acids.

Formulations/PreparationsHemimellitene is a mixture of the 1,2,3-isomer with up to 10% of related aromatics such as the 1,2,4-isomer
応用分野 · 4 件

解説トリメチルベンゼン (英: Trimethylbenzene) とは、化学式C9H12で表される芳香族炭化水素です。 分子量は120.19です。特異臭のある無色の液体です。ベンゼン環の3個の水素がメチル基で置き換わった構造で、3種類の異性体があります。1つ目は、ベンゼン環にメチル基が1位、2位、3位に付いた1,2,3-トリメチルベンゼンで、慣用的にヘミメリテン (英: Hemimellitene) と呼ばれます。2つ目は、ベンゼン環にメチル基が1位、2位、4位に付いた1,2,4-トリメチルベンゼンで、プソイドクメン (英: Pseudocumene) とも言われます。3つ目は、ベンゼン環にメチル基が1位、3位、5位に付いた1,3,5-トリメチルベンゼンで、 (英: Mesitylene) とも呼ばれます。いずれもタール軽油の高沸点留分から得られます。

用途染料、顔料、医薬品、工業薬品原料

使用Raw material for chemical synthesis.

使用用途トリメチルベンゼンは、顔料、染料、医薬品、そして工業薬品の合成原料として主に使用されています。 1,2,4-トリメチルベンゼンは、ガソリン添加剤としても利用されています。また、SD溶剤 (イソドデカンとの混合物で、発泡スチロール減容化溶剤) としても知られています。 1,3,5-トリメチルベンゼンは、高沸点溶媒としても使用されます。また、エレクトロニクスの分野では、半導体ウェハー (半導体集積回路: ICチップの材料となる、半導体物質の結晶でできた円形の薄い板) の写像形成の際の (精密な電路を作るといった用途で用いられる加工法) として用いられています。

調製方法

合成方法石油のクレavageプロセスなどから得られる。

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関連反応

22 件

関連ノート

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