化工社化工社 化学情報印刷レポート · 研究参考用
3,5-ジメチルフェノール
3,5-ジメチルフェノール · 1,3,5-キシレノール · 3,5-キシレノール · sym-m-キシレノール · ヒドロキシキシレン · 3,5-キシレノル · 3,5-キシレノ-ル · ３，５ジメチルフェノル
識別子と物理属性
| CAS No. | 108-68-9 |
|---|---|
| 分子式 | C8H10O |
| 平均分子量 | 122.16 g/mol |
| 単同位体質量 | 122.07316494 g/mol |
| SMILES | Cc1cc(C)cc(O)c1 |
| InChIKey | TUAMRELNJMMDMT-UHFFFAOYSA-N |
| PubChem CID | 7948 |
| ChEMBL | CHEMBL191740 |
| ChEBI | CHEBI:38572 |
| EC No. | 203-606-5 |
| DTXSID | DTXSID1025148 |
| 現地名 | 3,5-ジメチルフェノール |
化学・物理的性質
| XLogP | 2.4 |
|---|---|
| 極性表面積 | 20.2 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 80.6 |
| 物質分類 | Other Classes -> Phenols |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| 香料 | Fragrance Ingredient (3,5-Dimethylphenol) -> IFRA transparency List |
| LogP（分配係数） | log Kow= 2.352.54 |
| 密度 | 0.968 at 68 °F (NTP, 1992) - Less dense than waterwill float0.9680 @ 20 °C/4 °C0.97 g/cm³1.115 |
| 香味料 | EU Flavoring substances |
| Viscosity | 2.42 mN.s.m-2 at 80 °C |
| Color/Form | Needles from waterNeedles from petroleum etherWhite crystals |
| 溶解度 | less than 1 mg/mL at 68 °F (NTP, 1992)Sol in ethyl alcohol, carbon tetrachlorideVery sol in benzene, chloroform, etherIn water, 4.88X10+3 mg/l @ 25 °C.4.0 x 10 (-2) mol/l, at pH 5.1 and 25 °C.Solubility in water, g/100ml at 25 °C: 0.55.3g/L(25℃) |
| 引火点 | [HSDB] 80 °C80 °C c.c.109 °C |
| 沸点 | 427.1 °F at 760 mmHg (NTP, 1992)219.5 °C219 °C222 °C(lit.) |
| Decomposition | When heated to decomp it emits acrid smoke and irritating fumes. |
| 融点 | 61-64 °C(lit.) |
| 蒸気圧 | 5-5.4Pa at 25℃ |
| 屈折率 | 1.5146 (estimate) |
| 貯蔵条件 | room temp |
| 外観・状態 | 結晶性固体 |
| pKa（酸解離定数） | pK1:10.15 (25°C) |
| 色 | 白からオレンジ |
| 臭い | Strong, “cresylic” odor. |
| Merck | 14,10082 |
| BRN | 774117 |
| ヘンリー定数 | 1.5×101 mol/(m3Pa) at 25℃, Brockbank (2013) |
| InChI | 1S/C8H10O/c1-6-3-7(2)5-8(9)4-6/h3-5,9H,1-2H3 |
| InChIKey | TUAMRELNJMMDMT-UHFFFAOYSA-N |
| SMILES | Cc1cc(C)cc(O)c1 |
| LogP（分配係数） | 2.35 at 25.5℃ |
| CAS データベース | 108-68-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Phenol, 3,5-dimethyl-(108-68-9) |
| EPAの化学物質情報 | 3,5-Dimethylphenol (108-68-9) |
安全性と法規制
| GHS 分類 | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P405, and P501 (click each P-code to see the statement)H301 (99.7%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P264+P265, P270, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P362+P364, P363, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: Phenol, 3,5-dimethyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Phenol, 3,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 3,5-dimethyl- 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: 24-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/1918Phenol, 3,5-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Xylenols: Human health tier II assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include corrosion of the mucous membranes, upper respiratory tract, skin, and eyesburning sensation, coughing, wheezing, laryngitis, and shortness of breath. Other symptoms may include severe irritation or burning of the eyes and skinirritation of the respiratory systemdizziness, stomach pain, exhaustion, and coma. It can cause headaches, nausea, and vomiting. It can also cause dermatitis, muscular weakness, dimness of vision, irregular and rapid breathing, ringing in the ears, weak pulse, dyspnea, and unconsciousness. It can damage the kidneys, liver, pancreas, and spleenand cause edema of the lungs. Inhalation may be fatal as a result of spasm, inflammation, and edema of the larynx and bronchichemical pneumonitisand pulmonary edema. Chronic exposure can lead to digestive disturbances, nervous disorders, and skin eruptions. |
| 有害性の概要 | Causes ataxia and muscle contraction/spasticity in lethal-dose testing of mice[RTECS] Toxic by ingestionA severe eye irritant[HSDB] A corrosive substance that can cause injury to the skin and eyesA respiratory tract irritant[ICSC] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitisMay be absorbed through skin[MSDSonline] As the six dimethylphenol isomers and the mixed isomer substance are generally similar in toxicity, a common TLV for these substances is appropriate. . . . In mice, oral exposure to 250 mg/kg/day produced changes in blood parameters including statistically significant decreases in mean corpuscular volume and mean corpuscular hemoglobin concentration (4 and 3% reduction in mean values, respectively. . . . Available data on skin sensitization from exposure to dimethylphenol are mixed but warrant the addition of a DSEN notation. . . . All six dimethylphenol isomers were tested in a mouse local lymph node assay and the results found 2.4, 2,5, and 3,4-dimethylphenol to be positive for skin sensitization. There are no epidemiology studies. In a case report, ingestion of about 250 ml of a mixture of dimethylphenol isomers resulted in CNS depression, hypotension, and death. [ACGIH] See Phenol. |
| 反応性グループ | Phenols and Cresols |
| EC 分類 | Symbol: TR: 24/25-34S: (1/2)-26-28-36/37/39-45 |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | Toxikologische Bewertung 139: 21 (1995). Summary and assessment of 3,5-xylenol.Environmental Protection Agency EPA/600/8-88/031 p.30 (1987). Health effects assessment for dimethylphenols. |
| Reactivity Profile | 3,5-DIMETHYLPHENOL is incompatible with bases, acid chlorides, acid anhydrides, and oxidizing agents. It corrodes steel, brass, copper, and copper alloys. (NTP, 1992) |
| Chemical Dangers | Reacts with acid anhydrides, acid chlorides, bases and oxidants. |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.Wear protective gloves when administering first aid. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rest. Do NOT induce vomiting. Refer for medical attention . |
| 応急処置 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| 安全保管 | Separated from acid anhydrides, acid chlorides, bases and oxidants. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| 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.Chemical Treatability of 3,5-DimethylphenolConcentration Process: Biological treatmentChemical Classification: PhenolsScale of Study: UnknownType of Wastewater Used: Pure compound (one solute in a solvent)Results of Study: 89.3% reduction based on chemical oxygen demandrate of biodegradation 11.1 mg chemical oxygen demand/g hr (activated sludge process).Concentration Process: Activated carbonScale of Study: Batch flow, Laboratory ScaleResults of Study: 100% reduction5% desorbed from carbon by elutriation with solvent. (Calgon FS-300 used. Solvents included pentane-acetone, diethylether, methylene chloride-acetone, chloroform-acetone, and acetone.) |
| 漏出処分 | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. |
| 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles, face shield or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Inhalation Risk | No 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. |
| 生態毒性値 | LC100 Tetrahymena pyriformis (protozoa ciliate) 2.3 mmole/l/24 hr /Conditions of bioassay not specified/TLm Carassius carassius (Crucian carp) 53 mg/l/24 hr /Conditions of bioassay not specified/TLm Tinca tinca (tench) 52 mg/l/24 hr /Conditions of bioassay not specified/TLm Salvelinus (trout embryos) 50 mg/l/24 hr /Conditions of bioassay not specified/ |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 190-1400(2), indicate that 3,5-dimethylphenol is expected to have low to moderate mobility in soil(SRC). Volatilization of 3,5-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.041 mm Hg(4) and water solubility of 4880 mg/l(5). 3,5-Dimethylphenol is not expected to volatilize from dry soil surfaces based upon a its vapor pressure(3). 3,5-Dimethylphenol has been reported to degrade from soil in 11 days at a temperature of 19 °C(6).AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 190-1400(2), indicate that 3,5-dimethylphenol is expected to adsorb in varying amounts to suspended solids and sediment in water(SRC). 3,5-Dimethylphenol may volatilize from water surfaces(3,SRC) based upon an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.041 mm Hg(4) and water solubility of 4880 mg/l(5). Estimated volatilization half-lives for a model river and model lake are 30 days and 225 days, respectively(3,SRC). However, this model underestimates the volatilization half-life of 3,5-dimethylphenol since it does not take into account the effects of adsorption. The Koc of 1,400(2) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half-life = 1,900 days in model pond) and one in which adsorption was ignored (half-life = 330 days in model pond)(6). According to a classification scheme(7), an estimated BCF of 36(3,SRC), from 3,5-dimethylphenol's log Kow(8), suggests bioconcentration in aquatic organisms is moderate(SRC). In humic waters, degradation by the reaction with peroxy radicals should ensue with a half-life on the order of hours(9). 3,5-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Biodegradation screening studies indicate that a 31% loss of theoretical oxygen demand occurred after 5 days(10,11). In addition, it has been reported that 3,5-dimethylphenol was readily degraded in St. Lawrence River water(12). Biodegradation under anaerobic conditions failed to occur after 24 days in one study using a river sediment inoculum(13), yet 45% degradation occurred after 8 weeks in another study using a contaminated groundwater digester(14).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,5-dimethylphenol, which has a vapor pressure of 0.041 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,5-dimethylphenol 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 3.4 hours(SRC) from its rate constant of 1.13X10-10 cu cm/molecule-sec at 25 °C(3). Atmospheric 3,5-dimethylphenol is known to be removed by rainwater(4). 3,5-Dimethylphenol has an absorption band at 281 nm (cyclohexane), and a shoulder may extend over 290 nm, thus making it a candidate for direct photochemical degradation(5,6). Night-time degradation in urban areas should occur rapidly through reaction with atmospheric nitrate radicals, as rate constants for this reaction with phenolic compounds are approximately 250 times faster than with hydroxyl radicals(7,SRC). |
| 食品調査値 | 3,5-Dimethylphenol was identified as a volatile component of floured chickpea (Cicer arietinum L.) seed(1), pork(2), bacon(3) and the Japanese dried food, Bonito(4). |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| 暴露経路 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| Signs and Symptoms | Cough. Dizziness. Headache.MAY BE ABSORBED! Burning sensation. Skin burns.Redness. Pain. Severe deep burns.Burning sensation. Abdominal pain. Nausea. Vomiting. Diarrhoea. Dizziness. Headache. Shock or collapse. |
| Effluent Concentrations | Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an estimated 3,5-dimethylphenol concn of 968 mg/l, (mixture with 3- and 4-ethylphenol)(1). 3,5-Dimethylphenol was identified but not quantified in leachate collected from a Swedish municipal landfill in May 1990(2). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | The Koc of 3,5-dimethylphenol in soils with an organic carbon content <0.15% ranged from 460-1400the Koc for 3,5-dimethylphenol in Dormont soil (organic carbon content = 1.5%) was determined to be 190(1). According to a classification scheme(2), these Koc values suggest that 3,5-dimethylphenol is expected to have moderate to low mobility in soil(SRC). |
| Natural Pollution Sources | CONSTITUENT OF ... AUTOMOBILE EXHAUST.Dimethylphenols, of which 3,5-dimethylphenol is an isomer, are present in the essential oils of various conifers, in tea, and in tobacco and tobacco smoke(1). |
| Atmospheric Concentrations | URBAN/SUBURBAN: In 1984, a gas phase concn of 3,5-dimethylphenol was detected in 7 of seven rain events in Portland, OR, at concns ranging from 9.7-42 ng/cu m, averaging 20 ng/cu mthe amount associated with adsorption to particulate matter was <5% of the gas phase concn in every case(1). 3,5-Dimethylphenol was detected at 1 ug/cu m in air outside an oil shale wastewater facility in Logan, WA, but not at a nearby undeveloped site in the oil shale region, or in urban Boulder, CO (detection limit = 0.05 ug/cu m)(2). SOURCE DOMINATED: Although found in gasoline and diesel motor exhaust, it was not detected in an Allegheny Mountain highway tunnel(3). |
| Human Toxicity Excerpts | TOXIC BY INGESTION AND SKIN ABSORPTION. /COMMERCIAL MIXTURES/ |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | ZE6475000 |
| 輸送番号（UN） | UN 2261 6.1/PG 2 |
| 税関コード | 29071400 |
| 危険文句（R） | 24/25-34 |
| 化審法 | (3)-521, (4)-57 |
| 危険表示 | T |
| 安全措置（S） | 26-28-36/37/39-45-28A |
| 危険等級 | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralEye Dam. 1Skin Corr. 1B |
| 包装等級 | II |
| 環境リスク評価 | 3,5-キシレノール(108-68-9) |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 108-68-9(Hazardous Substances Data) |
用途
用途
抗酸化剤?医薬?農薬(殺虫剤?除草剤)?可塑剤原料
使用
3,5-Dimethylphenol finds application as adhesives, sealant chemicals, plating and surface treating agents. It is also used as a solvent for cleaning or degreasing. Further, it is employed as a chemical intermediate for antioxidants, phenolic resins, active pharmaceutical ingredients and metaxalone (muscle relaxant).
一般的な説明
Colorless to off-white crystalline solid. Odor threshold 1 ppm. Taste threshold 0.001 mg/L.
製法・合成法
純化方法
Purify it as for 3,4-dimethylphenol. [Beilstein 6 IV 3141.]