基本情報
- 標準SMILES
Cc1ccc(C)c(C)c1- InChIKey
GWHJZXXIDMPWGX-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
1,2,4-trimethylbenzene appears as a liquid. Flash point near 130 °F. Less dense than water and insoluble in water. Vapors irritate eyes, throat, and nose. Used in dyes and pharmaceuticals.
名称と識別子
- 優先名称
- 1,2,4-Trimethylbenzene
- IUPAC
- 1,2,4-trimethylbenzene
- 現地名
- 水質分析用標準溶液 1,2,4-トリメチルベンゼン (1mg/mL メタノール溶液)
- 英語名
- 1,2,4-Trimethylbenzene
- 分子式
- C9H12
- 分子量
- 120.19
名称と別名
名称をさらに表示
データベース識別子
- CAS
95-63-6- PubChem CID
- 7247
- DTXSID
DTXSID6021402- ChEMBL
CHEMBL1797280- ChEBI
CHEBI:34039- UNII
- 34X0W8052F
- EC Number
- 202-436-9
- Nikkaji
- J3.567J
物性
構造計算による物性
- XLogP
- 3
- 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
- 形式電荷
- 0
- 複雑度
- 86
実験および物理化学的性質
Chemical Classes
Flammable agents - 2nd degree
Volatile Organic Compound (VOC)
LogP
log Kow = 3.78
3.63
3.8
Density
0.889 (USCG, 1999) - Less dense than water; will float
0.8758 g/cu cm at 20 °C; 0.8718 g/cu cm at 25 °C
Relative density (water = 1): 0.88
0.8758 @ 20°C
0.88
Solubility
0.006 % (NIOSH, 2024)
Miscible with ethanol, benzene, ethyl ether, acetone, carbon tetrachloride, petroleum ether
In water, 57 mg/L at 25 °C
0.057 mg/mL at 25 °C
Solubility in water: very poor
0.006%
Flash Point
111 °F (USCG, 1999)
44 °C
112 °F (44 °C) (Closed cup)
44 °C c.c.
112 °F
物理化学的性質
- 融点
- -44 °C · -44 °C
- 沸点
- 168 °C · 168 °C(lit.)
- 比重(密度)
- 0.876 g/mL · 0.876 g/mL at 20 °C(lit.)
- 蒸気密度
- 4.1 · 4.1 (vs air)
- 蒸気圧
- 4.5 mm · 4.5 mm Hg ( 37.7 °C)
- 屈折率
- 20 · n20/D 1.504(lit.)
- 闪点
- 120 °F · 120 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 0.057 g/リットル · 0.057g/リットル
- 外見
- 液体
- 酸解離定数(Pka)
- 14 · >14 (Schwarzenbach et al., 1993)
- 色
- 無色透明
- 臭い (Odor)
- 芳香の匂い
- 臭気閾値(Odor Threshold)
- 0.12 ppm · 0.12ppm
- 爆発限界(explosive limit)
- 0.8 · 0.8-7%(V)
- 水溶解度
- アルコール、ベンゼン、エーテルに可溶。水にわずかに溶ける
- 比熱容量
- 1.79 J/ · Cp(liquid): 1.79 J/(g·K), at 25℃
- Merck
- 14 · 14,7915
- BRN
- 1903005 · 1903005
- Henry's Law Constant
- 6.946 · 6.946, 11.202, and 15.702 at 27.0, 35.0, and 45.0 °C, respectively (dynamic headspace, Hansen et al., 1995)
- Dielectric constant
- 2.4 · 2.4(16℃)
- 安定性
- 安定。強力な酸化剤とは相容れない。可燃性。空気と爆発性混合物を形成する可能性があります。
- 化粧品成分の機能
- 溶媒
- InChI
- 1S/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3
- InChIKey
- GWHJZXXIDMPWGX-UHFFFAOYSA-N
- SMILES
- Cc1ccc(C)c(C)c1
- LogP
- 3.63 · 3.630
- 表面張力
- 29.3 mN/m · 29.3mN/m at 298.15K
- CAS データベース
- 95 · 95-63-6(CAS DataBase Reference)
- EPAの化学物質情報
- 1 · 1,2,4-Trimethylbenzene (95-63-6)
化学的性質
化学的特性colourless liquid. Insoluble in water, soluble in ethanol, ether and benzene.
化学性质立体規則性を有するが,アタクチックな構造を有しており,非晶性高分子。ガラス転移温度は約100℃であり,常温常圧で非晶質なガラス状態の熱可塑性高分子
安全と法規制
GHS分類
GHS Classification
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, 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 0.4% (13 of 3204) of reports.
Danger
H226 (99.6%): Flammable liquid and vapor [Warning Flammable liquids]
危険有害性情報
Regulatory Information
Chemical: Benzene, 1,2,4-trimethyl-
Hazard Traits - Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity
Benzene, 1,2,4-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,2,4-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: 21-01-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13135
Benzene, 1,2,4-trimethyl-: HSNO Approval: HSR001382 Approved with controls
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.)
Fire Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Flammable. Above 44 °C explosive vapour/air mixtures may be formed.
Fire Potential
MODERATE FIRE RISK.
IN ABSENCE OF PRECAUTIONS, FLAMMABLE CONCN OF VAPOR MAY BE PRESENT WHERE LIQUIDS ARE USED IN SOLVENT & THINNER OPERATIONS. /TRIMETHYL BENZENE/
Hazards Summary
A skin, eye, and respiratory tract irritant; Inhalation of high concentrations can cause CNS depression; [HSDB] A skin, eye, and respiratory tract irritant; May cause chemical pneumonitis after aspiration; Defats the skin; May have effects on the central nervous system and blood; [ICSC] Reported blood dycrasias in chronically exposed workers were probably caused by benzene present as a contaminant; [ACGIH] An irritant; [MSDSonline] See Trimethyl benzene isomers.
The major hazards encountered in the use and handling of 1,2,4-trimethylbenzene stem from its toxicologic properties. Toxic by inhalation and dermal contact, exposure to this liquid may occur from its use as a solvent and paint thinner, and in the manufacture of dyes, perfumes, resins, pharmaceuticals, and trimellitic anhydride. Effects from exposure may include headache, fatigue, nausea, irritation of the skin, eyes, and mucous membranes, central nervous system depression, asthmatic bronchitis, chemical pneumonitis, or pulmonary edema. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. While this substance must be moderately heated before ignition will occur (autoignition temperature: 932 °F), caution should be taken to prevent its heavier-than-air vapor from accumulating to flammable concentrations (flammable limits by volume: 0.9% to 6.4%). Water spray may be used to extinguish fires involving this substance.
TSCA Requirements
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. 1,2,4-Trimethylbenzene is included on this list. Effective date 4/29/1983; Sunset date 4/29/1993.
安全と保護具
Fire Fighting
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Use alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
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
Excerpt from NIOSH Pocket Guide for 1,2,4-Trimethylbenzene:
(General first aid procedures)
Fire Fighting Procedures
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/
Storage Conditions
Prior to working with this chemical you should be trained on its proper handling and storage. Before entering a confined space where this chemical may be present, check to make sure that an explosive concentration does not exist. Trimethylbenzene must be stored to avoid contact with oxidizers (such as perchlorates, peroxides, permanganates, chlorates, and nitrates), and strong oxidizers (such as chlorine, bromine, and fluorine) since violent reactions occur. Store in tightly closed containers in a cool, well-ventilated area away from heat. Sources of ignition such as smoking and open flames are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard. Metal containers involving the transfer of 5 gallons or more of this chemical should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. /Trimethyl benzenes/
STORAGE TANKS SHOULD BE MOUNDED TO CONFINE ESCAPING LIQUID & ESCAPE FROM PROCESS VESSELS SHOULD BE CONTROLLED IN SIMILAR MANNER BY SILLS @ DOORWAYS, DESIGN OF FLOORS, ETC. /TRIMETHYLBENZENES/
Cleanup Methods
Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. Keep this chemical out of a confined space ... because of the possibility of an explosion ... It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable. /Trimethyl benzenes/
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incineration /SRP: with appropriate emission controls/. /Trimethyl benzenes/
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. Do NOT let this chemical enter the environment.
Preventive Measures
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.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
毒性情報
Interactions
... The toxicokinetics of 124TMB was studied in nine 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 2 ppm (11 mg/cu m) of 124TMB during exposure to 300 mg/cu m of white spirit. The 124TMB isomer was analysed in blood, urine and exhaled air by gas chromatography. The DMHA metabolites of all three TMB isomers were analysed in urine by high-performance liquid chromatography. The results were compared with previously published exposures to 2 and 25 ppm (120 mg/cu m) of 124TMB vapor alone. ... Blood levels of 124TMB and excretion rates of 3,4-DMHA in urine were markedly elevated both during and after exposure to white spirit compared to the same exposure level of 124TMB alone. ... It appears that components in white spirit interfere with the metabolic elimination of 124TMB. This should be considered in biological exposure monitoring as well as in risk assessment.
Target Organs
Developmental
Eyes, skin, respiratory system, central nervous system, blood
Ecotoxicity Values
EC50; Species: Daphnia magna (Water flea, age 4-6 days, 1.5 mm); Conditions: freshwater, static, 23 °C, pH 6-7, dissolved oxygen 5-9 mg/L; Concentration: 30 mmol/cu m for 48 hr (95% confidence interval: 13-69 mmol/cu m); Effect: intoxication, immobilization
LC50; Species: Artemia salina (Brine shrimp, nauplii); Conditions: saltwater, static, 20 °C; Concentration: 100 mmol/cu m for 24 hr /> or =97% purity/
LC50; Species: Elasmopus pectinicrus (Scud, adult); Conditions: saltwater, renewal, 23 °C, salinity 30 ppt; Concentration: 5230 ug/L for 24 hr (95% confidence interval: 4890-5620 ug/L)
LC50; Species: Elasmopus pectinicrus (Scud, adult); Conditions: saltwater, renewal, 23 °C, salinity 30 parts per thousand; Concentration: 4910 ug/L for 48 hr (95% confidence interval: 4500-5340 ug/L)
For more Ecotoxicity Values (Complete) data for 1,2,4-TRIMETHYLBENZENE (9 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), a Koc value of 537 measured in soil(2), indicates that 1,2,4-trimethylbenzene is expected to have low mobility in soil(SRC). Volatilization of 1,2,4-trimethylbenzene is expected to be important from moist soil surfaces(SRC) given a measured Henry's Law constant of 6.16X10-3 atm-cu m/mole(3) and from dry soil surfaces(SRC) based on a measured vapor pressure of 2.1 mm Hg at 25 °C(4). Complete removal of 1,2,4-trimethylbenzene from sterile sandy loam soil samples contaminated with jet fuel was reported within 5 days, probably due to evaporation(5). Non-volatilized 1,2,4-trimethylbenzene may be subject to biodegradation(SRC). 1,2,4-Trimethylbenzene was degraded within 7 days during a study of the aerobic microbial degradation of components of gas oil in aqueous solution; this was demonstrated while contaminated water percolated through an unsaturated soil column(6).
AQUATIC FATE: Based on a recommended classification scheme(1), a Koc value of 537 measured in soil(2), indicates that 1,2,4-trimethylbenzene is expected to adsorb to suspended solids and sediment in water(SRC). 1,2,4-Trimethylbenzene is expected to volatilize from water surfaces(3) based on a measured Henry's Law constant of 6.16X10-3 atm-cu m/mole(4). Using this Henry's Law constant 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(5), BCF values of 31 to 275(6), measured in fish, suggest that bioconcentration in aquatic organisms is moderate to high(SRC). Biodegradation under aerobic conditions may be an important fate process for this compound in water although high concentrations of 1,2,4-trimethylbenzene may be toxic to the indigenous microbial population(6,7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,4-trimethylbenzene, which has a measured vapor pressure of 2.10 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2,4-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 about 12 hours(SRC), calculated from its rate constant of 3.25X10-11 cu cm/molecule-sec at 25 °C(3). 1,2,4-Trimethylbenzene also reacts with nitrate radicals in the atmosphere(4); the half-life for this reaction in air is estimated as 6-30 days(SRC), calculated from rate constants in the range of 5.4X10-16 to 2.70X10-15 cu cm/molecule-sec at 25 °C(4). 1,2,4-Trimethylbenzene does not contain chromophores that absorb at wavelengths >290 nm(5) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
1,2,4-Trimethylbenzene was reported as a component of pineapple guava (at 0.06 ug/g)(1), fried beef liver (88-125 ppb)(2), margarine (31.3 ppb)(2), butter (22.9 ppb)(2), cake doughnuts (94.3 ppb)(2), roasted filberts(3), in scrambled eggs from both fresh and supermarket eggs (trace levels)(4), chickpea seed(5) and fresh nectarines (trace levels)(6). 1,2,4-Trimethylbenzene is a volatile component of chicken, beef, and pork flavors(7).
Exposure Routes
The substance can be absorbed into the body by inhalation.
inhalation, ingestion, skin and/or eye contact
Signs and Symptoms
Confusion. Cough. Dizziness. Drowsiness. Headache. Sore throat. Vomiting.
Redness. Dry skin.
Redness. Pain.
See Inhalation.
irritation eyes, skin, nose, throat, respiratory system; bronchitis; hypochromic anemia; headache, drowsiness, lassitude (weakness, exhaustion), dizziness, nausea, incoordination; vomiting, confusion; chemical pneumonitis (aspiration liquid)
Effluent Concentrations
1,2,4-Trimethylbenzene was detected in automobile exhaust; reported concn for mixture of sec- and tert-butylbenzene and 1,2,4-trimethylbenzene was 6.1 ppm(1). Automobile exhaust from an English car without a catalytic converter contained 1,2,4-trimethylbenzene at 3717 ppb(2). Highway tunnel exhaust air in Hamburg, Germany (Elbtunnel) contained 1,2,4-trimethylbenzene at concns from 47.6 to 59.8 ug/cu m(3). Highway tunnel exhaust air in Belgium (The Craeybeckx tunnel) in March/April 1991 contained 1,2,4-trimethylbenzene at an average concn of 15 ug/cu m(4). Automobile exhaust from a light-duty vehicle contained 1,2,4-trimethylbenzene at concns ranging from 1.13 to 3.33 wt% of total non-methane hydrocarbons(5). Gasoline engine exhaust from a light-duty vehicle both with and without a catalytic converter contained 1,2,4-trimethylbenzene at 1.8 and 1.9 wt% of total organic gas emissions, respectively(6). Unburned gasoline in the summertime contained 3.2 wt% 1,2,4-trimethylbenzene(6).
1,2,4-Trimethylbenzene at 40 mg/10 minutes was introduced into water by a four-stroke outboard motor(1). The concn of 1,2,4-trimethylbenzene in the water of a canal to a harbor of Lake Constance, Germany, varied throughout the day with 7, 53, 507, 380, 518, 557, 557, and 614 ng/L reported for times 8:30, 9:37, 10:37, 11:40, 12:42, 15:20, 16:20, and 17:30 (1). A 7 and 10 horsepower outboard motor produced 7.9 and 24.2 ppm 1,2,4-trimethylbenzene, respectively, in 30 minutes in 160 liters water(2). 1,2,4-Trimethylbenzene was reported as one of the 99 most frequently detected compounds at Superfund sites(3). 1,2,4-Trimethylbenzene was detected in the gas emitted from a sludge landfill simulator at unreported concns(4). Emissions from a municipal waste incineration plant contained 1,2,4-trimethylbenzene at 1.17 ug/cu m(5). Emissions from coal-fired power stations in France contained 1,2,4-trimethylbenzene at 3.0 to 26.8 ug/Normalized cu m(6).
1,2,4-Trimethylbenzene was detected in leachate samples from 6 of 6 hazardous waste landfills at concns from 10 to 3160 ug/L and in 5 of 5 leachate samples from domestic landfills at concns of 0.94 to 8.1 ug/L(1). 1,2,4-Trimethylbenzene was detected at 10 ug/L in the effluent from the Los Angeles County wastewater treatment plant(2). 1,2,4-Trimethylbenzene was detected in secondary effluent from the South Fort Polk Sewage Treatment Plant, Louisiana, at 0.034 and 0.084 ug/L(3). Influent to the Jones Island publicly-owned treatment plant contained 1,2,4-trimethylbenzene from 7 to 12 ppb; effluent contained less than 1 ppb(4). Effluent samples from an in situ coal gasification experiment in Hanna, WY contained 1,2,4-trimethylbenzene from not detected (detection limit = 0.1 ppb) to 267 ppb(5). Dissolved air flotation treatment effluent from a class B petroleum refinery contained 1,2,4-trimethylbenzene at 178 ng/g(6). Two of six mixed household waste samples contained 1,2,4-trimethylbenzene at unreported concns(7). Effluent samples collected from advanced waste treatment plants in Pomona, CA (in 1974/1975) and Orange County, CA (in 1976) contained 1,2,4-trimethylbenzene at unreported concns(8).
Off-gas from two Ontario municipal wastewater treatment plants, Skyway in Burlington and Highland Creek in Metropolitan Toronto contained 1,2,4-trimethylbenzene at maximum concns of 499 and 471 ug/cu m, respectively; emission rates of 64 and 198 g/d were estimated(1). Leachate from the North Bay, Ontario landfill contained 1,2,4-trimethylbenzene at concns of 0.6 to 220 ug/L(2). 1,2,4-Trimethylbenzene was detected in 5 of 5 hazardous waste landfill leachate samples (10-3160 ug/L) and 4 of 4 sanitary landfill leachate samples (0.94-8.1 ug/L); landfills are located in Germany(3). 1,2,4-Trimethylbenzene was detected in 13.8% of stormwater samples collected in the state of North Carolina at a mean concn of 0.13 ug/L and max concn of 0.76 ug/L(4).
法規制情報
TSCA Requirements
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. 1,2,4-Trimethylbenzene is included on this list. Effective date 4/29/1983; Sunset date 4/29/1993.
State Drinking Water Guidelines
(CA) CALIFORNIA 330 ug/l
(FL) FLORIDA 35 ug/L
(NH) NEW HAMPSHIRE 330 ug/L
(WI) WISCONSIN 480 ug/l /Trimethylbenzenes/
安全データ
- OEB
- A
- OEL
- TWA: 25 ppm (125 mg/m3)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- DC3325000
- ridadr
- UN 3295 3/PG 3
- 毒性
- LD50 i.p. in male, female mice (mg/kg): 5000, 4100 (Janik-Spiechowicz)
- PRTR法
- 第一種指定化学物質
- hs_code
- 29029090
- risk_code
- 10-20-36/37/38-51/53-39/23/24/25-23/24/25-11-65
- 化審法
- (3)-7, (3)-3427 優先評価化学物質
- 安衛法
- 57,57-2
- 消防法
- 危-4-2-III
- hazard_code
- Xn,N,F,Xi,T
- hazard_note
- Irritant/Flammable
- safety_code
- 26-61-45-36/37-16-7-62
- hazard_class
- 3
- packing_group
- III
- 自然発火温度
- 959 °F
- 環境リスク評価
- 1,2,4-トリメチルベンゼン(95-63-6)
- Hazard Classifications
- Acute Tox. 4 InhalationAquatic Chronic 2Asp. Tox. 1Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 95-63-6(Hazardous Substances Data)
化学と産業
薬理情報
Biological Half-Life
... 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
Metabolism of 1,2,4-TMB in humans and animals occurs by side-chain oxidation to form alcohols and carboxylic acids or hydroxylation to phenols, which are then conjugated with glucuronic acid, glycine, or sulphates prior to urinary excretion ... . Both in laboratory animals and in humans, it was identified that 1,2,4-TMB metabolism is mainly directed towards isomeric dimethylbenzoic acids ... . In rats, 1,2,4-TMB metabolism leads to the production of isomeric dimethylbenzoic acids, of which 3,4-dimethylbenzoic acid was identified as the most prominent in the urine . ... 3,4-Dimethylhippuric acid has been reported to be a minor metabolite in humans ... . This metabolite has also been observed in rabbits, in addition to 2,4-dimethylbenzoic acid... .
Single doses of 1,2,4-trimethylbenzene (124TMB) or 14C-124TMB were administered orally to rats for metabolism and distribution studies. ... A complex mixture of isomeric trimethylphenols, dimethylbenzyl alcohols, dimethylbenzoic acids and dimethylhippuric acids excreted in the urine accounted for more than 81% of the administered dose. The major metabolites were 3,4-dimethylhippuric acid (30.2% dose), 2,4-dimethylbenzyl alcohol (12.7% dose, primarily as sulfate and glucuronide conjugates) and 2,5-dimethylbenzyl alcohol (11.7% dose, primarily as sulfate and glucuronide conjugates).
A study was undertaken of the mercapturic acid metabolism of 1,2,4-trimethylbenzene in the rat. Of three regioisomeric dimethylbenzyl mercapturic acids, i.e. 2,4-, 2,5- and 3,4-dimethylbenzyl isomers, the third isomer was not found in the urinary mercapturic acid isolated by preparative HPLC, from the comparison of NMR spectrum of the isolate with those of authentic specimens. The urinary mercapturate was then assigned to 2,4- and/or 2,5-dimethylbenzyl isomers. The excretion rate of the mercapturic acid was 14-20% of dose as 2,4-dimethylbenzyl isomer.
... the metabolism of pseudocumene (1,2,4-trimethylbenzene) was investigated in rabbits. After oral administration of this compound, urine was collected for several days and analyzed for the presence of acidic metabolites. ... Two major urinary metabolites were identified namely 2,4-dimethylbenzoic acid and 3,4-dimethylhippuric acid. The presence of these acidic metabolites in urine is a good indication of exposure to pseudocumene.
For more Metabolism/Metabolites (Complete) data for 1,2,4-TRIMETHYLBENZENE (8 total), please visit the HSDB record page.
Absorption, Distribution and Excretion
Absorption of 1,2,4,-TMB in humans following respiratory exposure has been reported to range from 56 to 71%... . Trimethylbenzenes have also been reported to be readily absorbed following oral exposure ... . In the bloodstream, approximately 85% of 1,2,4-TMB is bound to red blood cells ... .. As it distributes to tissues in humans, 1,2,4-TMB tends to accumulate in adipose and fatty tissues, brain tissue, and perirenal fat, due to its lipophilicity ...
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. ...
Single doses of 1,2,4-trimethylbenzene (124TMB) or 14C-124TMB were administered orally to rats for metabolism and distribution studies. 14C-124TMB was rapidly and widely distributed throughout the body with the highest levels in adipose tissue. No other preferential uptake of 14C-124TMB by any of the organs or tissues examined was evident. Tissue levels declined rapidly within 24 hr after dosage, with more than 99% of the administered radioactivity recovered in the urine during this period. A complex mixture of isomeric trimethylphenols, dimethylbenzyl alcohols, dimethylbenzoic acids and dimethylhippuric acids excreted in the urine accounted for more than 81% of the administered dose.
... Male Wistar rats were exposed to pseudocumene vapors at nominal concentrations of 25, 100 or 250 ppm in the dynamic inhalation chambers for 6 hr. Blood samples were collected during (between 1st and 6 th hr) and after exposure (between 6 th min and 6 th hr). Blood concentrations of pseudocumene were estimated by gas chromatography using the headspace technique. During a six-hour exposure, the concentration of pseudocumene in blood increased rapidly within the first 2 hr reaching then a plateau. The elimination of pseudocumene from blood followed an open two-compartment model. Urine samples were collected from the exposed animals, and metabolites were analyzed by gas chromatography with a flame ionization detector. Three metabolites were measured in the rat urine after hydrolysis: 3,4-dimethylbenzoic acid (3,4-DMBA), 2,4-dimethylbenzoic acid (2,4-DMBA) and 2,5-dimethylbenzoic acid (2,5-DMBA). A significant linear correlation was found between the level of exposure and the concentration of dimethylbenzoic acids. The enzyme kinetics of pseudocumene biotransformation was calculated by Lineweaver-Burk equation. Metabolic constants, Km (mg/L) and Vmax (mg/hr/kg), the parameters for pseudocumene biotransformation by rats were estimated (3,4-DMBA - Km = 28, Vmax = 96; 2,4-DMBA - Km = 7, Vmax = 25; 2,5-DMBA - Km = 7, Vmax = 23).
For more Absorption, Distribution and Excretion (Complete) data for 1,2,4-TRIMETHYLBENZENE (10 total), please visit the HSDB record page.
用途と製造
Uses
Used for sterilizing catgut; as a solvent in manufacture of dyes, perfumes and resins; solvent for liquid scintillation counting solutions; in the manufacture of trimellitic anhydride, pharmaceuticals, pseudocumidine, and pyromellitic dianhydride; as a comonomer for pseudocumene-formaldehyde resins; as an industrial solvent and paint thinner; as vermifuge; [HSDB] Used in high octane fuels; It is present in gasoline and occurs in coal tar and many petroleum products. [CHEMINFO] See Trimethyl benzene, isomers.
Petroleum Production and Refining [Category: Industry]
Solvent for /classical/ liquid scintillation counting solutions.
Sterilizing catgut ... solvent in manufacture of dyes, perfumes and resins; solvent for liquid scintillation counting solutions
Manufacture of trimellitic anhydride, dyes, pharmaceuticals & pseudocumidine
CHEM INT FOR PYROMELLITIC DIANHYDRIDE.
U.S. Imports
(1980) 5.10X10+9 GRAMS
(1981) 5.41X10+9 GRAMS
U.S. Production
2023: 100,000,000 - <250,000,000 lb
(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS
(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS
1,2,4-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#5343]
Methods of Manufacturing
From C9 fraction of refinery reformate streams by fractional distillation.
Trimethylbenzene fraction (fractionation; coproduced with mesitylene/durene)
... Pseudocumene ... /is/ found in coal tar oil ... /It/ can be isolated by distillation and purified by the differential hydrolysis of ... /its/ sulfonic acids. More important industrially is the occurrence of trimethylbenzenes in some mineral oils, and their formation during processing of crude oil, especially catalytic cracking and reforming. Psuedocumene is obtained in 99% purity by superfractionation from the C9 cut of crude oil refining. Pseudocumene ... can be obtained by extractive crystallization of the C9 cut with urea.
Trimethylbenzenes, especially pseudocumene and mesitylene, are ... formed by liquid-phase disproportionation of xylene in the presene of aluminum chloride. These reactions can be carried out in the gas phase at high temperature on aluminum silicate catalysts.
For more Methods of Manufacturing (Complete) data for 1,2,4-TRIMETHYLBENZENE (6 total), please visit the HSDB record page.
Household Products
Cosmetics product ingredient: 1,2,4-Trimethylbenzene (Trimethylbenzene)
Information on 284 consumer products that contain 1,2,4-Trimethylbenzene in the following categories is provided:
General Manufacturing Information
Transportation Equipment Manufacturing
Benzene, 1,2,4-trimethyl-: ACTIVE
応用分野
用途ガソリン添加剤、無水トリメリット酸、SD溶剤、染料、香料などの原料として使用される。
説明1,2,4-Trimethylbenzene (mesitylene) is an aromatic hydrocarbon compound commonly present in commercial solvents encompassing their boiling range. Mesitylene are the most common isomer used in commercial applications. Aromatic hydrocarbons in hydrocarbon solvents are predominantly alkylated one ring structures as well as two aromatic ring structures which may also be alkylated.
使用1,2,4-Trimethylbenzene is the unlabelled version of 1,2,4-Trimethyl 13C6-benzene (T796173), a labelled aromatic standard.
一般的な説明A liquid. Flash point near 130°F. Less dense than water and insoluble in water. Vapors irritate eyes, throat, and nose. Used in dyes and pharmaceuticals.
調製方法
合成方法スチレンを重合して得られる。一般にラジカル重合によって製造される
純化方法Reflux pseudocumene over sodium and distil it under reduced pressure. [Beilstein 6 H 1088, 6 I 542, 6 II 1072, 6 III 6278, 6 IV 7339.]
上流・下流製品情報
上流原料
下流製品
補足説明
定義ChEBI: 1,2,4-trimethylbenzene is a trimethylbenzene carrying methyl groups at positions 1, 2 and 4. It has a role as a neurotoxin.
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関連ノート
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