1,2,3-Trimethylbenzene

HCID 10686CAS 25551-13-7

Basic information

Standard SMILES
Cc1cccc(C)c1C
InChIKey
FYGHSUNMUKGBRK-UHFFFAOYSA-N
Molecular formula
C9H12
Average molar mass
120.19 g/mol
Monoisotopic mass
120.09390038

Overview

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.

Names & identifiers

Preferred name
1,2,3-Trimethylbenzene
IUPAC
1,2,3-trimethylbenzene
English name
trimethylbenzene
Molecular formula
C9H12
Molecular weight
120.19

Names & synonyms

1,2,3-TRIMETHYLBENZENE526-73-8HemimelliteneHemellitolHemimellitolZK4R7UPH6RNSC-5167DTXCID7027750CHEBI:34037RefChem:53594208-394-8Trimethylbenzene
Show more names
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%

Database identifiers

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

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
9

Experimental & physicochemical properties

Chemical ClassesVolatile Organic Compound (VOC)
SolventsSolvents -> Aromatic Solvents
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesPesticide -> EPA IRIS
LogP · 3 items

log Kow = 3.66

3.7

3.78

OdorDistinctive, aromatic odor

Physicochemical properties

Melting point
-68.52 °C · -68.52°C (estimate)
Boiling point
159.22 °C · 159.22°C (estimate)
Density
0.8803 · 0.8803 (estimate)
refractive index
1.5 · 1.5000 (estimate)
form
Colorless liquid
Exposure limits
20 ppm · EU LTEL: 20 ppm(100 mg/m3)

Safety & regulation

GHS classification

GHS Classification · 6 items

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.

Hazard information

Regulatory Information · 4 items

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 items

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.

Safety & protection

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 items

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 items

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/

Toxicology

Target Organs · 2 items

Hematologic

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

Ecotoxicity Values · 3 items

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 items

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 items

The substance can be absorbed into the body by inhalation.

inhalation, ingestion, skin and/or eye contact

Regulatory information

TSCA Requirements · 2 items

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.

Safety data

OEB
A
OEL
TWA: 25.0 ppm; 125.0 mg/m3
tsca
TSCA listed
ridadr
2325
Signal word
Warning
Symbol(GHS)
GHS07,GHS02

Chemistry & industry

Pharmacology

Biological Half-Life · 1 item

... 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 items

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 items

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

Uses & manufacturing

Uses · 6 items

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 items

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 items

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

Applications

UsesRaw material for chemical synthesis.

UsesAs a raw material in chemical syntheses; as ultraviolet stabilizers in plastics; found in solvents and as a constituent of gasoline.

Suppliers26 total

济南新晨化工有限公司15318808971 15318808971
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]
茂名市雄大化工有限公司18607606943 13929797612
山东铭宇供应链管理有限公司0531-18615601 18615601385
湖北鑫杰成化工科技有限公司13554075426 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

22 records

Linked notes

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