化工社化工社 化学情報印刷レポート · 研究参考用
ベンゼンチオール
ベンゼンチオール · 1-ベンゼンチオール · チオフェノール · メルカプトベンゼン · フェニルメルカプタン · チオフェノル · チオフェノ-ル · ベンゼンチオル
識別子と物理属性
| CAS No. | 108-98-5 |
|---|---|
| 分子式 | C6H6S |
| 平均分子量 | 110.18 g/mol |
| 単同位体質量 | 110.01902119 g/mol |
| SMILES | Sc1ccccc1 |
| InChIKey | RMVRSNDYEFQCLF-UHFFFAOYSA-N |
| PubChem CID | 7969 |
| ChEMBL | CHEMBL119405 |
| ChEBI | CHEBI:48498 |
| EC No. | 203-635-3 |
| DTXSID | DTXSID7026811 |
| 現地名 | ベンゼンチオール |
化学・物理的性質
| XLogP | 2.5 |
|---|---|
| 極性表面積 | 1 |
| 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 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 46.1 |
| 物質分類 | Other Classes -> ThiolsFlammable agents - 3rd degree |
| pH | Feebly acidic5 (20°C in H2O, saturated aqueous solution) |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP（分配係数） | log Kow = 2.52 |
| 臭い | Repulsive, penetrating, garlic-like odor, especially when impure不快 |
| 食品添加物 | FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 1.0728 at 77 °F (EPA, 1998) - Denser than waterwill sink1.0775 g/cu cm at 20 °CRelative density (water = 1): 1.071.073-1.0801.073 @25 °C1.078 |
| 香味料 | EU Flavoring substances |
| Color/Form | Water-white liquid |
| 溶解度 | 0.08 % at 77 °F (NIOSH, 2024)In water, 835 mg/L at 25 °CWater solubility of 836 mg/l at 25 °C.In water, 470 mg/L at 15 °CVery soluble in alcoholmiscible with ether, benzene, carbon disulfideSoluble in ethanol, ethyl ether, benzeneslightly soluble in carbon tetrachlorideDMSO、酢酸エチル不溶性 |
| 引火点 | 127 °F (USCG, 1999)50 °C (122 °F) (Closed cup)132 °F123 °F |
| 沸点 | 334.9 °F at 760 mmHg (EPA, 1998)169.1 °C169.00 °C. @ 760.00 mm Hg168 °C169 °C46.4 °C (10mm Hg)336 °F169 °C(lit.) |
| 融点 | -15 °C |
| 蒸気密度 | 3.8 (vs air) |
| 蒸気圧 | 1.4 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.588(lit.) |
| FEMA | 3616 | BENZENETHIOL |
| 貯蔵条件 | Store at RT. |
| pKa（酸解離定数） | 6.6(at 25℃) |
| 外観・状態 | 液体 |
| 色 | 無色透明～微黄色透明 |
| においのタイプ | 肉の風味 |
| 比熱容量 | Cp(liquid): 1.57 J/(g·K), at 25℃ |
| Merck | 14,9355 |
| JECFA Number | 525 |
| BRN | 506523 |
| ヘンリー定数 | 2.9×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 誘電率 | 4.4(25℃) |
| 安定性 | 安定。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。悪臭。強力な酸化剤とは相容れない。 |
| 主な用途 | 農業洗浄剤化粧品環境フレーバーそして香料食品および飲料パーソナルケア |
| InChI | 1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H |
| InChIKey | RMVRSNDYEFQCLF-UHFFFAOYSA-N |
| SMILES | Sc1ccccc1 |
| LogP（分配係数） | 2.33 |
| CAS データベース | 108-98-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzenethiol(108-98-5) |
| EPAの化学物質情報 | Thiophenol (108-98-5) |
化学的特性
Colorless or pale yellowish mobile liquid. Insoluble in water, soluble in alcohol and oils.
化学性质
色から淡黄色の，悪臭を有する液体．沸点168.3℃，融点?14.8℃．水に不溶
安全性と法規制
| GHS 分類 | DangerH226 (99.8%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P332+P317, P361+P364, P362+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1653 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard] |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| 規制情報 | Chemical: BenzenethiolBenzenethiol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenethiol 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: 01-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10117Thiophenol: HSNO Approval: HSR003057 Approved with controlsThe 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.) |
| 輸送ラベル（DOT） | Poison Inhalation Hazard Flammable Liquid |
| 火災危険 | When heated to decomposition or on contact with acids, it emits toxic fumes of sulfur oxides. May be ignited by heat, sparks or flames. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Unstable, oxidizes in air. Avoid contact with acids. (EPA, 1998)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | Flammable liquid |
| 健康有害性 | Marked potential for causing eye changes. May cause death (EPA, 1998)· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| 有害性の概要 | Phenyl mercaptan causes tearing of the eyesit is a skin and respiratory irritant. Volunteers tolerate 1.5 ppm for 5 minutes (eye irritation), 8 ppm for 10 seconds (eye irritation), and a single breath of 35 ppm (nasal irritation). [ACGIH] Inhalation may cause CNS effects[ICSC] Liquid is corrosive to skin. [CHRIS] Corrosive to skin[Quick CPC] See THIOLS.The major hazards encountered in the use and handling of thiophenol stem from its toxicologic properties and flammability. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this clear-to-white, garlic-smelling liquid may occur from its manufacture and use as a chemical intermediate for insecticides, acaricides, fungicides, pharmaceuticals, and polymers. Effects from exposure may include contact burns to the skin and eyes, headaches, eye changes, and methemoglobin formation. OSHA has set a time-weighted average (TWA) limit of 0.5 ppm, as a final rule to become effective December 31, 1992. Local exhaust ventilation should be used to control thiophenol in workplace air. In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus and chemical protective clothing which is specifically recommended by the shipperor producer. If contact should occur, irrigate eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing and shoes should be removed and left at the site. Thiophenol may be ignited by heat, sparks, or flames, and may form explosive concentrations in confined spaces such as sewers. For fires involving thiophenol, extinguish with dry chemical, CO2, water spray, fog, or regular foam. Fight such fires from a maximum distance and dike fire control water for later disposal. Thiophenol may be transported domestically via air, rail, road, and water, in containers bearing the label, "Poison." For small spills of thiophenol, take up with sand or other noncombustible absorbent and place into containers for later disposal. Large spills should be diked far ahead for later disposal. |
| 輸送番号・ガイド（DOT） | 2337 131 |
| FDA 要件 | Thiophenol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. |
| 反応性グループ | Sulfides, Organic |
| UN 分類 | UN Hazard Class: 6.1UN Subsidiary Risks: 3UN Pack Group: I |
| Special Reports | DHEW/NIOSHOccupational exposure to n-alkane mono thiols, cyclohexanethiol and benzenethiolDHEW (NIOSH) Pub 78-213: 129 pp (1978). A review, with 143 references, of thio exposure std & safety, biological effects of exposure to thiols, & sampling & analysis of thiols in the environment.Spafford RB, Dillon HKAnalytical Methods Evaluation and Validation for Vinylidene fluoride, Vinyl bromide, Vinyl fluoride, Benzenethiol, and n-Octanethiol 70 pp (1981) Iss SORI-EAS-81-405PB83-133447. Analytical methods were evaluated & validated for benzenethiol in air. |
| 消火 | Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing.Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| 応急処置措置 | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| 漏出応急措置 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 応急処置 | Signs and Symptoms of Acute Thiophenol Exposure: Acute exposure to thiophenol may result in cough, difficulty in breathing, irritation of the lungs, and pneumonia. Nausea, vomiting, and diarrhea are often seen. Contact with thiophenol may result in irritation and redness, pain, inflammation, and severe burns to the skin, eyes, and mucous membranes.General First Aid:(General first aid procedures) |
| 安全保管 | Separated from strong oxidants, strong acids and food and feedstuffs. |
| Firefighting Hazards | Special hazards arising from the substance or mixture: Carbon oxides, sulphur oxides. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA).TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016]. |
| 消火手順 | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Phenyl mercaptan/Suitable extinguishing media: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spraysolid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.Use water spray to cool unopened containers. |
| 保管条件 | Conditions for safe storage, including any incompatibilities: Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. |
| 清掃方法 | Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Phenyl mercaptan/Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Phenyl mercaptan/Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment.Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: |
| 処分方法 | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P014, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.Incineration: Dissolve in a combustible solvent such as alcohols, benzene, etc. Burn in the furnace with after scrubber to neutralize sulfur dioxide.The following wastewater treatment technologies have been investigated for thiophenol: Concentration process: Biological treatment.For more Disposal Methods (Complete) data for THIOPHENOL (6 total), please visit the HSDB record page. |
| 相互作用 | 1. Sulphur mustard reacts directly with benzenethiols and cysteine esters in aqueous medium. 2. Benzenethiols diffuse into lung slices in short term culture. 3. Treatment of lung slices in short term culture with benzenethiols does not protect cellular glutathione from conjugation with sulphur mustard. 4. Following uptake of cysteine ester into lung slices cysteine is elevated but this does not protect cellular glutathione from sulphur mustard. /benzenethiols/ |
| 標的器官 | Eyes, skin, respiratory system, central nervous system, kidneys, liver, spleen |
| 生態毒性値 | LC100 bluegill sunfish 6 hr 5 mg/L/Conditions not stated/LC100 trout 1 hr 5 mg/L /Conditions not stated/LD50 Wild bird oral 24 mg/kgLC100 yellow perch 3 hr 5 mg/L/Conditions not stated/LC100 goldfish 23 hr 5 mg/L/Conditions not stated/ |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 230(SRC), determined from a structure estimation method(2), indicates that thiophenol is expected to have moderate mobility in soil(SRC). The pKa of thiophenol is 6.62(3), indicating that this compound will exist partially as an anion in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the anion form of thiophenol from moist soil surfaces is not expected because anions do not volatilize(SRC). Volatilization of the neutral form of thiophenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.35X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 1.93 mm Hg(5), and water solubility, 835 mg/L(6). Thiophenol in its neutral form is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Thiophenol, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(7). However, in water, using an activated sludge inocula, thiophenol reached 30-42% of its theoretical BOD in 6 days(8). These studies suggest that biodegradation in soil may or may not be an important fate process(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 230(SRC), determined from a structure estimation method(2), indicates that thiophenol is expected to adsorb to suspended solids and sediment(SRC). A pKa of 6.62(3) indicates thiophenol will exist partially in the anion form at pH values of 5 to 9 and, therefore, volatilization of the anion form from water surfaces is not expected to be an important fate process(SRC). Volatilization of the neutral form from water surfaces is expected(4) based upon an estimated Henry's Law constant of 3.35X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 1.93 mm Hg(5), and water solubility, 835 mg/L(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for the neutral form for a model river and model lake are 6 hours and 5 days, respectively(SRC). Thiophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). According to a classification scheme(7), an estimated BCF of 20(SRC), from its log Kow of 2.52(8) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thiophenol, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(9). However, in water, using an activated sludge inocula, thiophenol reached 30-42% of its theoretical BOD in 6 days(10). These studies suggest that biodegradation in aquatic systems may or may not be an important fate process(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiophenol, which has a vapor pressure of 1.93 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase thiophenol 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 34 hours(SRC), calculated from its rate constant of 1.12X10-11 cu cm/molecule-sec at 25 °C(3). Thiophenol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| 有害作用 | Other Poison - Chemical Asphyxiant |
| 暴露経路 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| 毒性の概要 | IDENTIFICATION AND USE: Thiophenol is a water-white liquid or prism-like crystal with a repulsive, penetrating odor similar to garlic, especially when impure. It is primarily used as a mosquito larvicide and chemical intermediate for pesticides, pharmaceuticals and amber dyes. HUMAN EXPOSURE AND TOXICITY: Thiophenols causes conversion of oxyhemoglobin to methemoglobin in human red blood cells and dose-dependent oxidative stress. ANIMAL STUDIES: Application of a drop to rabbit eyes caused severe irritation, moderate redness, chemosis of the conjunctiva with discharge for 3-4 days. Corneas developed opacities which gradually increased during 2-3 wk, becoming opalescent and obscuring details of pupil and iris. However, in 2 months the eyes recovered. Thiophenol administration in rats during gestation increased postimplantation loss, decreased the live litter size, decreased fetal body weight/litter, and increased the incidence of external malformations in the high dose group. In summary, maternal toxicity, observed as maternal mortality, a persistent decrease in body weight and weight gain, and decreased in food consumption during the treatment period occurred at the high dose level of 50 mg/kg/day. Rooting behavior was observed in all thiophenol groups during the dosing period indicating an aversion to the dosing formulation. Rooting behavior showed a dose-related increase and an earlier onset with increasing dose. The lowest observed-adverse-effect-level (LOAEL) was 20 mg/kg/day for maternal toxicity based upon minor, transient decreases in maternal weight gain & food consumption on gestation day 6-9. In another experiment in Sprague Dawley rats, F0 and F1 liver and kidney weights increased with increasing dose of thiophenol and were associated with centrilobular hepatocellular hypertrophy and renal tubule degeneration. Decreased (5-6%) sperm motility was observed in Sprague Dawley F0 rats administered 18 and 35 mg/kg. Inhibited spermiation was observed in all treated F1 males but not the F0 males. In developmental study in rabbits NOAEL for developmental toxicity was > or = 40 mg/kg/dayThe NOAEL for maternal toxicity was 10 mg/kg/day. Thiophenol, in Salmonella typhimurium tester strains TA100 and TA98, showed relative mutagenic response with and without metabolic activation. |
| Signs and Symptoms | Cough. Headache. Nausea. Sore throat.MAY BE ABSORBED! Redness. Pain.Redness. Pain. Blurred vision.See Inhalation.irritation eyes, skin, respiratory systemdermatitiscyanosiscough, wheezing, dyspnea (breathing difficulty), pulmonary edema, pneumonitisheadache, dizziness, central nervous system depressionnausea, vomitingkidney, liver, spleen damage |
| Ongoing Test Status | EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assaysClick on the "Chemical Explorer" button on the tool bar to see the data./[USEPAICSS Dashboard ApplicationAvailable from, as of June 27, 2014: http://actor.epa.gov/dashboard/]The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of October 20, 2014: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=108-98-5] |
| Effluent Concentrations | Thiophenol has been identified in the effluent from a petroleum refining industry(1). Thiophenol was detected as a minor component of pyrolysis of eucalyptus kraft lignin(2). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of thiophenol can be estimated to be 230(SRC). According to a classification scheme(2), this estimated Koc value suggests that thiophenol is expected to have moderate mobility in soil. The pKa of thiophenol is 6.62(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). The sorption coefficient for thiophenol to snow was measured as log Ki 3.65 cu m/sq m(5). |
| Human Toxicity Excerpts | /ALTERNATIVE and IN VITRO TESTS/ Thiophenol and aminothiophenol were used to study levels of toxicity in human red blood cells. Thiophenols caused conversion of oxyhemoglobin to methemoglobin. Reduction of corresponding disulfides by intracellular glutathione caused cyclic reduction/oxidation reactions, resulting in increased oxidative flux. Three levels of oxidative stress were observed in these experimentsthe lowest level resulted from incubation with 0.25 mM thiophenolthe intermediate level with 0.50 mM thiophenol or 0.25 mM 4-aminothiophenolthe highest levels with 0.50 mM 4-aminothiophenol. Methemoglobin formation increased with increasing level of oxidative stress. Glycolysis and the hexose monophosphate shunt were inhibited at the intermediate and highest levels of stress, respectively. Above the highest level of stress non-intact hemoglobin was formed and cell lysis occurred. These metabolic responses were reflected in cellular levels of NADH, NADPH and reduced glutathione. At the lowest level of oxidative stress, both glycolysis and hexose monophosphate shunt were increased such that near-normal levels of NADH, NADPH and reduced glutathione were maintained and methemglobin formation was kept to a minimum. The response of red cells to 0.25 mM thiophenol appears to represent a level of oxidative stress to which the cell is capable of adaptive metabolic response. Glycolysis contributes approximately one quarter of the total reducing equivalents from glucose metabolism in response to the oxidative challenge by thiophenol. |
| RCRA 要件 | P014As stipulated in 40 CFR 261.33, when thiophenol, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)). |
| TSCA 要件 | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzenethiol is included on this list. Effective date: 03/07/86Sunset date: 03/07/96.Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 1/26/94Reporting date: 3/28/94. |
| CERCLA 報告数量 | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Thiophenol is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lb. |
| F | 10-13-23 |
| 職業暴露限界（OEL） | Ceiling: 0.1 ppm (0.5 mg/m3) [15-minute] |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DC0525000 |
| 輸送番号（UN） | UN 2337 |
| 毒性 | bird - wild,LD50,oral,24mg/kg (24mg/kg),Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. |
| PRTR法 | 第1種指定化学物質 |
| 税関コード | 29309099 |
| 危険文句（R） | 10-24/25-26-41-36/37/38 |
| 化審法 | 一般化学物質 |
| 安衛法 | 57,57-2 |
| 消防法 | 危険物第4類第三石油類(非水溶性) |
| 危険表示 | T+,T |
| hazard_note | Toxic/Stench |
| 安全措置（S） | 23-26-28-36/37/39-45-28A-16 |
| 危険等級 | 6.1Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 3Repr. 2Skin Irrit. 2 |
| 包装等級 | I |
| 毒劇物取締法 | II |
| 自然発火温度 | 450 °C |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 108-98-5(Hazardous Substances Data) |
用途
解説
チオフェノールとは、ベンゼン環上の1つの水素をチオール基 (-SH) で置換した構造の液体です。 芳香族化合物の1種で「ベンゼンチオール」や「フェニルメルカプタン」「メルカプトベンゼン」とも呼ばれています。常温で無色透明または淡黄色の液体で腐った卵のような特徴的な臭気をもちます。水には不溶ですが、およびによく溶けます。 毒物及び劇物取締法では毒物に指定されており、短期間の暴露でも強い眼刺激や皮膚刺激などを引き起こす恐れがあるため、取り扱う際は十分な注意が必要です。 消防法では第4類第2石油類非水溶性液体、PRTR法では第1種指定化学物質に該当します。有機則は非該当です。
用途
医薬品、農薬用原料、有機合成中間体、重合防止剤、酸化防止剤、ゴム素練促進剤
天然物の起源
Reported found in cooked/boiled beef.
使用
Thiophenol is used as a mosquito larvicideand as an intermediate in organic synthesis.It is effective in reducing peroxide formationin jet fuels (Watkins et al. 1989).
一般的な説明
A clear liquid with a repulsive odor. Boiling point 168.3°C. Insoluble in water and denser than water. Very toxic by ingestion, skin absorption, and by inhalation. Used as a chemical intermediate and in mosquito control.
使用用途
チオフェノールの主な用途は、医薬品、農薬用原料、有機合成中間体、重合防止剤、酸化防止剤です。ほかの化学物質の原料になることが多く、人工光合成の研究における電子源やプロトン源として使用されることもあります。 チオフェノールの具体的な用途としては、以下の様な例が挙げられます。 1. 求核剤 チオフェノールのチオール基は酸解離定数が比較的小さいことから、求核剤として機能します。この性質を利用することで、保護基の脱保護などが可能になります。 2. 脱離基 チオフェノールは脱離基としても機能します。 3. 光合成の研究における電子源およびプロトン源 酸性度が高いチオフェノールは、電子やプロトンの供給源としても機能します。
製法・合成法
製造方法
By reduction of benzenesulfonyl chloride with zinc dust in sulfuric acid.
製造方法
チオフェノールには主に「Freunderberg-Schonberg (フロインターベルク・シェーンベルク) 反応」によって合成されます。これは原料であるフェノールをチオカルバメート化またはチオカーボネート化した後に、熱転位によってフェノール由来の酸素原子を硫黄原子に置換し、最後にアルカリ加水分解することでチオフェノールを合成するという手法です。本反応はフェノールの芳香環上の水素原子が他の置換基になっている場合でも用いることが出来ます。 また工業製品の場合は、引火点を下げるためにが混ざっていることもあります。
合成方法
モノクロロベンゼンと硫化水素との高温での反応