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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 8368作成日：2026年10月27日

2,6-ジクロロトルエン

2,6-ジクロロトルエン · 1,3-ジクロロ-2-メチルベンゼン · 2,6-ジクロロ-1-メチルベンゼン · 2，6ジクロロトルエン · 2,6‐ジクロロトルエン · 1,3-DICHLORO-2-METHYLBENZENE · DICHLOROTOLUENE MIXTURE · orotoL

https://huagongshe.com/ja/chemical/8368

2,6-ジクロロトルエン の分子構造式

識別子と物理属性

CAS No.118-69-4
分子式C7H6Cl2
平均分子量161.03 g/mol
単同位体質量159.98465555 g/mol
SMILESCc1c(Cl)cccc1Cl
InChIKeyDMEDNTFWIHCBRK-UHFFFAOYSA-N
PubChem CID8368
ChEMBLCHEMBL3182206
EC No.204-269-7
DTXSIDDTXSID3040697
現地名2,6-ジクロロトルエン

化学・物理的性質

XLogP4.3
極性表面積0
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82.9
物質分類Other Classes -> Halogenated Monoaromatics
SpringerMaterials PropertiesDielectric constant
LogP（分配係数）Log Kow = 4.29
密度1268.6 kg/cu m @ 20 °CLiquid density = 1.254 g/cu cm at 20 °C1.28 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.001.254 g/mL at 25 °C(lit.)
溶解度Soluble in chloroformInsoluble in water.Solubility in water, g/100ml at 25 °C: (very poor)26mg/l 不溶24mg/L（20℃）
引火点82 °C
沸点198 °C @ 760 mm Hg196-203 °C(lit.)
融点25.8 °C2.8 °C2 °C
蒸気圧0.35 [mmHg]Vapor pressure, Pa at 25 °C: 3434Pa at 25℃
屈折率Index of refraction: 1.5507 @ 20 °C/Dn20/D 1.55(lit.)
Physical DescriptionLiquidmp = 2.8 deg C[eChemPortal: SIDSUNEP] Colorless liquid[MSDSonline]COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.
Other Experimental PropertiesThe use of global and substituent physicochemical structure descriptors for quantitative structure-property relationship studies has been evaluated through direct and autocorrelated applications. Partial least squares analysis has been used to predict the partition coefficient for octanol/water, log P, for chlorinated alkylbenzenes. This investigation revealed that various of the physicochemical parameters considered were highly correlated with the partition coefficient and that partial least squares models based on global, direct or autocorrelated substituent parameters all seem to be adequate for prediction of log P, as compared to results obtained experimentally or by means of standard substituent calculation schemes. However, the use of autocorrelation vectors of connectivity, steric and electronic effects may be preferably due to a high degree of explanation of the molecular descriptor variance.
貯蔵条件Store below +30°C.
外観・状態液体
色無色透明～微黄色透明
BRN1907194
ヘンリー定数2.3×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
InChI1S/C7H6Cl2/c1-5-6(8)3-2-4-7(5)9/h2-4H,1H3
InChIKeyDMEDNTFWIHCBRK-UHFFFAOYSA-N
SMILESCc1c(Cl)cccc1Cl
LogP（分配係数）4.25 at 25℃
CAS データベース118-69-4(CAS DataBase Reference)
NISTの化学物質情報Benzene, 1,3-dichloro-2-methyl-(118-69-4)
EPAの化学物質情報2,6-Dichlorotoluene (118-69-4)

化学的特性

clear colorless to slightly yellowish liquid

安全性と法規制

GHS 分類This chemical does not meet GHS hazard criteria for 0.9% (1 of 114) of reports.DangerH302 (36.8%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 114 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報Chemical: Benzene, 1,3-dichloro-2-methyl-Status: Active Update: 26-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/13588Benzene, 1,3-dichloro-2-methyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
火災危険Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 82 °C explosive vapour/air mixtures may be formed.
火災の可能性Combustible /Dichlorotoluene/
有害性の概要Histopathological changes to liver and kidney observed in feeding study with ratsFemale rats exhibited atrophy of the thymus at the higher doses (300 and 1000 mg/kg)Reproductive toxicity (decrease in implantation number and viability four days after birth and abnormal nursing) was observed in feeding study with ratsNo evidence of mutagenicity[eChemPortal: SIDSUNEP] An irritant[MSDSonline]The major hazards encountered in the use and handling of 2,6-dichlorotoluene stem from its toxicologic properties and flammability. Exposure to 2,6-dichlorotoluene may be via inhalation or dermal routes, primarily resulting from occupational activities, including those associated with production and use as a high boiling solvent, and its production and use as a chemical intermediate in the manufacture of dyestuffs and herbicides. Because it is a strong irritant, personnel involved with 2,6-dichlorotoluene should wear boots, protective gloves, and goggles. Avoid breathing vapor, or, before entering a contaminated area, wear a full-face mask self-contained breathing apparatus which provides eye protection. Broken packages containing 2,6-dichlorotoluene should not be handled without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. While this substance must be moderately heated before ignition occurs, 2,6-dichlorotoluene is nevertheless considered a combustion hazard. For fires involving 2,6-dichlorotoluene, extinguish with alcohol foam, carbon dioxide, dry chemical, or water in flooding quantities as fog (solid streams of water may be ineffective). This substance should be stored away from sparks, flames, and other sources of ignition, even though it is considered normally stable even under fire exposure conditions. Shipping regulations and other DOT regulatory requirements should be consulted before transport. If a 2,6-dichlorotoluene spill occurs, keep material out of water sources and sewers by building dikes to contain the flow, as necessary. Use water spray to knock down vapor. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.

用途

用途

医薬?染料原料 (NITE CHRIP)

使用

2,6-Dichlorotoluene is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.

製法・合成法

製造方法

2,6-Dichlorotoluene is obtained from the Sandmeyer reaction on 2-amino-6-chlorotoluene, ring chlorination and desulfonylation of p-toluene sulfonyl chloride, and from the chlorination and dealkylation of 4-tert-butyltoluene or 3,5-di-tert-butyltoluene.

純化方法

Fractionally distil it and collect the middle fraction. [Beilstein 5 IV 815.]

UN 分類UN Hazard Class: 9UN Pack Group: III
Chemical DangersDecomposes on heating. This produces carbon monoxide, chlorine and hydrogen chloride. Reacts violently with strong oxidants and strong bases.
DOT Emergency Guidelines/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Chlorotoluenes//GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Chlorotoluenes//GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Chlorotoluenes//GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Chlorotoluenes/For more DOT Emergency Guidelines (Complete) data for 2,6-DICHLOROTOLUENE (8 total), please visit the HSDB record page.
Hazard Classes and CategoriesAcute Tox. 4 (36.8%)Flammable liquids - Category 4
Standard Transportation Number49 131 48Chlorotoluenes
Shipment Methods and RegulationsNo person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Shipping Name/ Number DOT/UN/NA/IMOUN 2238ChlorotoluenesIMO 3.3
Skin, Eye, and Respiratory Irritations... Strong irritant /4-Chlorotoluene/
消火Use powder, water spray, carbon dioxide.
応急処置措置Fresh air, rest.Rinse and then wash skin with water and soap.Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth.
安全保管Provision to contain effluent from fire extinguishing. Separated from strong bases and strong oxidants. Cool. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access.
消火手順If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Chlorotoluenes/
処分方法SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
漏出処分Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Remove vapour with fine water spray.
Preventive MeasuresIf material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Chlorotoluenes/Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Chlorotoluenes/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.
Eye PreventionWear safety goggles.
Fire PreventionNO open flames. Above 82 °C use a closed system and ventilation.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
環境中動態TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 5,100(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 2,6-dichlorotoluene will be immobile in soil(SRC). Volatilization of 2,6-dichlorotoluene may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.2X10-3 atm-cu m/mole(SRC), using a recommended regression equation(4), and from dry soil surfaces(SRC) based on an estimated vapor pressure of 0.36 mm Hg(SRC), using a fragment constant method(5). Based on limited data, 2,6-dichlorotoluene may be resistant to biodegradation under anaerobic conditions(SRC). 2,6-Dichlorotoluene, at 1000 uM, was not readily biodegraded in an anoxic soil slurry30-35% biodegradation was reached after 150 days(6).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 5,100(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that 2,6-dichlorotoluene should adsorb to suspended solids and sediment in water(SRC). 2,6-Dichlorotoluene may volatilize from water surfaces based on an estimated Henry's Law constant of 4.2X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Estimated half-lives for a model river and model lake are 4 hours and 5 days, respectively(1,SRC). An estimated BCF value of 1,100(1,SRC), from a measured log Kow(2), suggests that 2,6-dichlorotoluene will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(4). Based on limited data, 2,6-dichlorotoluene may be resistant to biodegradation under anaerobic conditions(SRC). 2,6-Dichlorotoluene, at 1000 uM, was not readily biodegraded in an anoxic soil slurry30-35% biodegradation was reached after 150 days(5).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,6-dichlorotoluene, which has an estimated vapor pressure of 0.36 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,6-dichlorotoluene 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 days(3,SRC).
有害作用Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Effluent ConcentrationsIn a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWS) sponsored by the Effluent Guidelines Division of the USEPA, 2,6-dichlorotoluene was identified in discharges of the following industrial category (frequency of occurrence, median concn in ppb): organic chemicals (1426.7), publicly owned treatment works (540.4)(1). The highest effluent concn was 1424 ppb in the paint and ink industry(1).
ICSC Environmental DataThe substance is toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment.
Soil Adsorption/MobilityThe Koc of 2,6-dichlorotoluene is estimated as approximately 5,100(SRC), using a measured log Kow of 4.29(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 2,6-dichlorotoluene will be immobile in soil(SRC).
Artificial Pollution Sources2,6-Dichlorotoluene's production and use as a chemical intermediate in the manufacture of dyestuffs and herbicides(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationBacterial strains isolated from a landfill site previously used for disposal of chlorinated organic wastes were able to utilize 2,6-dichlorotoluene(1). 2,6-Dichlorotoluene, at 1000 uM, was not readily biodegraded in an anoxic soil slurry30-35% biodegradation was reached after 150 days(2).
Environmental BioconcentrationAn estimated BCF value of 1100 was calculated for 2,6-dichlorotoluene(SRC), using a measured log Kow of 4.29(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will occur(SRC).
Volatilization from Water/SoilThe Henry's Law constant for 2,6-dichlorotoluene is estimated as 4.2X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 2,6-dichlorotoluene will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 4 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 5 days(2,SRC). This rate may be attenuated by adsorption to sediment and particulate matter in the water(SRC). 2,6-Dichlorotoluene's estimated values for vapor pressure, 0.36 mm Hg(3,SRC), and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces may occur(SRC).
Non-Human Toxicity ExcerptsA method was developed to analyze rat tissue, fat and blood for some chlorinated compounds found in an extract of soil from an industrial waste site. Extraction with hexane and ethyl ether-hexane (1 + 1) was followed by concentration over steam, and gas chromatographic analysis with an electron capture detector. Volatile compounds were analyzed in a glass column coated with 6% SP-2100 plus 4% OV-ll on Chromosorb W. Semivolatile compounds, chlorinated compounds and pesticides were analyzed in a 70 m glass capillary column coated with 5 OV-101. Phenols were analyzed in a glass column packed with 1% SP-1240 DA on Supelcoport. The most efficient means of separation was to use the same glass column for volatile compounds, a DB-5 fused silica capillary column for semivolatile compounds, pesticides and phenols, and the same 1% SP-1240 DA glass column for separation of beta-BHC and pentachlorophenol. Recoveries ranged from 86.3 + or - 9.1% (mean + or - SD) to 105 + or - 10.4%. Sensitivities for semivolatile chlorinated compounds, pesticides and phenols were 4 ng/g for fat, 1 ng/g for tissue and 0.2 ng/ml for blood. Sensitivities for volatile compounds were 4-fold higher (16, 4 and 0.8, respectively). Sensitivities for dichlorobenzenes and dichlorotoluenes were 8 ng/g for fat, 2 ng/g for tissue and 0.4 ng/ml for blood.
Environmental Abiotic Degradation2,6-Dichlorotoluene reacts with photochemically-produced hydroxyl radicals in the atmosphere by addition to the aromatic ring and H-atom abstraction. The rate constant for the vapor-phase reaction of 2,6-dichlorotoluene with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 2,6-Dichlorotoluene has an absorption band at 274 nm that extends to about 300 nm(2)it is therefore a candidate for direct photolysis by sunlight. No information concerning photolysis rates could be foundhowever on irradiation with shorter UV light in dry, nitrogen purged methanol, rapid dehalogenation occurs(3).
Probable Routes of Human ExposureExposure to 2,6-dichlorotoluene would be primarily occupational via inhalation and dermal contact. (SRC)
水環境危害等級（WGK）2
TSCA 収載状態TSCA listed
輸送番号（UN）UN 2810
税関コード29036990
危険文句（R）22-23-37/38-40-41-36/37/38
化審法(3)-78
消防法危-4-3-III
危険表示T,Xi,Xn
hazard_noteHarmful
安全措置（S）26-36/37/39-45-24/25-37/39
危険等級9Aquatic Chronic 2
包装等級III
貯蔵分類10 - Combustible liquids
有害物質データ118-69-4(Hazardous Substances Data)