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チオアセトアミド
チオアセトアミド · エタンチオアミド · アセトイミドチオ酸 · 1-イミノエタンチオール · チオアセトアミド STANDARD · チオアセトアミド, ACS · チオアセトアミド Standard, 1000 µg/mL in Acetonitrile · チオアセトアミド, ACS, 99% min
識別子と物理属性
| CAS No. | 62-55-5 |
|---|---|
| 分子式 | C2H5NS |
| 平均分子量 | 75.14 g/mol |
| 単同位体質量 | 75.01427016 g/mol |
| SMILES | CC(N)=S |
| InChIKey | YUKQRDCYNOVPGJ-UHFFFAOYSA-N |
| PubChem CID | 2723949 |
| ChEMBL | CHEMBL38737 |
| ChEBI | CHEBI:32497 |
| EC No. | 200-541-4 |
| DTXSID | DTXSID9021340 |
| 現地名 | チオアセトアミド |
化学・物理的性質
| XLogP | -0.3 |
|---|---|
| 極性表面積 | 58.1 |
| 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 | 4 |
| 形式電荷 | 0 |
| 複雑度 | 33 |
| 物質分類 | Other Classes -> Sulfur CompoundsCarcinogens |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP（分配係数） | log Kow = -0.26-0.46/-0.36 |
| 臭い | Slight odor of mercaptans |
| Color/Form | Crystals from benzeneColorless leafletsYellow tabletsCRYSTALS FROM ALC, PLATES FROM ETHER |
| 溶解度 | 5 to 10 mg/mL at 68 °F (NTP, 1992)In ethanol 26.4 g/100 gsparingly sol in etherMiscible in benzeneMISCIBLE IN PETROLEUM ETHERIn water, 1.63X10+5 mg/l @ 25 °C.Solubility in water: goodpasses test 2%16.3g/100mL(25℃) |
| Decomposition | When heated to decomposition, it emits very toxic fumes of /nitrogen oxides and sulfur oxides/. |
| 融点 | 234 to 237 °F (NTP, 1992)113-114 °C113-116 °C115.5 °C108-112 °C (lit.) |
| 臭気閾値 | Medium odor threshold level: 94.7 ppm in 50% aqueous ethylene glycol. |
| 蒸気圧 | 15.2 [mmHg] |
| Physical Description | Thioacetamide appears as white crystals with a mercaptan odor.Colorless solid[ICSC] Colorless or yellow solid with a mild odor of mercaptans[HSDB] White solid[CAMEO] Colorless crystalline solid with an odor of rotten eggs[Alfa Aesar MSDS]COLOURLESS CRYSTALS WITH CHARACTERISTIC ODOUR. |
| Stability/Shelf Life | RELATIVELY STABLE COMPD IN NEUTRAL AQ SOLN |
| 沸点 | 111.7±23.0 °C(Predicted) |
| 密度 | 1.37 |
| 屈折率 | 1.5300 (estimate) |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 外観・状態 | 固体 |
| pKa（酸解離定数） | 13.25±0.29(Predicted) |
| 色 | オフホワイトからややベージュ |
| pH | 5.2 (100g/l, H2O, 20℃) |
| Merck | 14,9319 |
| BRN | 506006 |
| ヘンリー定数 | 1.5×100 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定性 水、鉱酸とは相容れない。 |
| InChI | 1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) |
| InChIKey | YUKQRDCYNOVPGJ-UHFFFAOYSA-N |
| SMILES | CC(N)=S |
| CAS データベース | 62-55-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Ethanethioamide(62-55-5) |
| EPAの化学物質情報 | Thioacetamide (62-55-5) |
化学的特性
Thioacetamide is combustible, crystalline compound. Slight mercaptan odor.
化学性质
融点112~114℃
安全性と法規制
| GHS 分類 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: EthanethioamideHazard Traits - CarcinogenicityStatus: Active Update: 30-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1779Thioacetamide: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| その他の安全情報 | IMAP assessments - Ethanethioamide: Human health tier II assessment |
| 火災危険 | Flash point data on this compound are not availableit is probably combustible. (NTP, 1992) |
| 健康有害性 | SYMPTOMS: The symptoms following exposure to this compound may include skin and eye irritation, liver damage, fatigue, nausea, eczema, central nervous system depression, acidosis, vomiting, respiratory depression, hypotension, unconsciousness, tremors, convulsions, anorexia and conjunctivitis. |
| 有害性の概要 | Reports of degenerative liver changes following ingestion of the juice of oranges dipped for 2-5 seconds in 5% solutionCirrhosis and other adverse changes (including tumors) of the liver observed in rats, mice, and dogs in feeding studies[HSDB] May cause liver injuryA possible human carcinogen[ICSC] A skin and eye irritant[eChemPortal: ESIS] A skin and strong eye irritant[Alfa Aesar MSDS] |
| 反応性グループ | Amides and Imides |
| EC 分類 | Symbol: TR: 45-22-36/38-52/53S: 53-45-61Note: E |
| Special Reports | REVIEW:[NEAL RA, HALPERT JTOXICOLOGY OF THIONO-SULFUR COMPOUNDSANNU REV PHARMACOL TOXICOL 22: 321 (1982)]National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Thioacetamide (62-55-5) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s172thio.pdf] |
| RCRA 要件 | U218As stipulated in 40 CFR 261.33, when thioacetamide, 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 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). |
| Reactivity Profile | THIOACETAMIDE reacts with aqueous acid to generate hydrogen sulfide. Forms addition compounds and sulfides with salts of heavy metals. Hydrolyzed by acids or bases (NTP, 1992). |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes of nitrogen oxides and sulfur oxides. |
| Packaging and Labelling | Do not transport with food and feedstuffs. |
| 消火 | Fires involving this chemical should 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.Remove contaminated clothes. 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. |
| 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 food and feedstuffs. |
| 保管条件 | PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/ |
| 清掃方法 | PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/ |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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 | 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.Thioacetamide is a potential candidate for incineration. Recommended incineration types: Rotary kiln with a temperature range 820 to 1600 °C and a residence time of hoursFluidized bed with a temperature range 840 to 1800 °C and a residence time of several seconds or longer.PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/For more Disposal Methods (Complete) data for THIOACETAMIDE (7 total), please visit the HSDB record page. |
| 漏出処分 | Personal protection: complete protective clothing including self-contained breathing apparatus. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | VENTILATION CONTROL: BASIC VENTILATION METHODS ARE LOCAL EXHAUST VENTILATION & DILUTION OR GENERAL VENTILATION.PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/For more Preventive Measures (Complete) data for THIOACETAMIDE (10 total), please visit the HSDB record page. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. |
| 相互作用 | DISTRIBUTION OF PU /SRP: plutonium/ IN RATS WAS INFLUENCED BY ORAL ADMIN OF THIOACETAMIDE (300 MG/KG). RATS INJECTED IP WITH PLUTONIUM CITRATE RETAINED 71.5 & 23.6% OF RECOVERED ACTIVITY IN THE CARCASS & LIVER, RESPECTIVELY, WHEREAS RATS WHICH HAD BEEN TREATED WITH THIOACETAMIDE 24 HR PREVIOUSLY CONTAINED 35.8 & 59.5% OF THE PU IN THE CARCASS & LIVER RESPECTIVELY.PHENOBARBITAL PRETREATMENT POTENTIATED HEPATIC NECROSIS PRODUCED BY THIOACETAMIDE.ADRENALECTOMY PROTECTED RATS AGAINST THE HEPATOTOXIC ACTION OF THIOACETAMIDE INJECTED IP AT 200 MG/KG BW. THIS PROTECTIVE EFFECT COULD BE REVERSED BY HYDROCORTISONE GIVEN TWICE DAILY INTRAPERITONEALLY AT 0.5 TO 2.5 MG/RAT.STROPHANTHIN-G PROTECTED RATS AGAINST LIVER NECROSIS CAUSED BY THIOACETAMIDE.For more Interactions (Complete) data for THIOACETAMIDE (10 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from an log Kow of -0.26(2) and a regression-derived equation(3), indicates that thioacetamide is expected to have very high mobility in soil(SRC). Volatilization of thioacetamide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of thioacetamide from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 15 mm Hg(SRC), determined from a fragment constant method(5). Thioacetamide was not biodegraded by activated sludge after 5 days(6), and therefore may be resistant to biodegradation in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from an log Kow of -0.26(2) and a regression-derived equation(3), indicates that thioacetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.4X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 days and 39 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thioacetamide was not biodegraded by activated sludge after 5 days(7), and therefore may be resistant to biodegradation in aqueous systems(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thioacetamide, which has an estimated vapor pressure of 15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase thioacetamide 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 18 hours(SRC), calculated from its rate constant of 21X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). |
| 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. |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion. |
| Medical Surveillance | PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/ |
| Soil Adsorption/Mobility | The Koc of thioacetamide is estimated as 17(SRC), using a log Kow of -0.26(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that thioacetamide is expected to have very high mobility in soil(SRC). |
| Natural Pollution Sources | Thioacetamide has not been reported to occur in nature. |
| Human Toxicity Excerpts | ...SEVERAL PEOPLE DEVELOPED DEGENERATIVE CHANGES IN LIVER FROM DRINKING JUICE OF ORANGES WHICH HAD BEEN IMMERSED FOR 2-5 SEC IN 5% SOLN OF THIOACETAMIDE TO PREVENT GROWTH OF BLUE & GREEN MOLDS. |
| Artificial Pollution Sources | Thioacetamide's production and use as a substitute for hydrogen sulfide in the laboratory(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Thioacetamide was not biodegraded by activated sludge after 5 days(1), and therefore may be resistant to biodegradation in the environment(SRC). |
| Carcinogen Classification | ThioacetamideGroup 2B: Possibly carcinogenic to humansVolume 7: (1974) Some Anti-thyroid and Related Substances, Nitrofurans and Industrial Chemicals1987 |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated for thioacetamide(SRC), using a log Kow of -0.26(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| 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 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| F | 10 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | AC8925000 |
| 輸送番号（UN） | 2811 |
| 毒性 | MLD orally in rats: 200 mg/kg (Ambrose) |
| PRTR法 | 第二種指定化学物質 |
| 税関コード | 29309070 |
| 危険文句（R） | 45-22-36/38-52/53 |
| 化審法 | (9)-806 |
| 危険表示 | T |
| 安全措置（S） | 53-45-61-99 |
| 危険等級 | 9Acute Tox. 4 OralAquatic Chronic 3Carc. 1BEye Irrit. 2Skin Irrit. 2 |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 有害物質データ | 62-55-5(Hazardous Substances Data) |
用途
解説
チオアセトアミド (英: Thioacetamide) とは、分子式C2H5NSで表される、チオアミドの一種の有機化合物です。 別名には、「アセトチオアミド」「エタンチオアミド」「アセトイミドチオ酸」などがあります。CAS登録番号は、62-55-5です。チオアセトアミド水溶液と多くの金属カチオンはそれぞれ対応する硫化物を作り、古典的定性分析で使われます。人体に対して有害な物質です。
用途
染料、 医薬?医薬中間体、合成中間体、写真薬
説明
Thioacetamide (TAA) is not known to occur in nature. It is prepared by heating ammonium acetate and aluminum sulfide.
使用
Thioacetamide is a carcinogen, a hepatotoxicant. Thioacetamide induces acute chronic liver injury through the activation of protein synthesis of RNA, DNA, and gamma-glutamyl transpeptitase. Thioacetamide has been used in the synthesis of [emailprotected] nano-array core-shell structure.
一般的な説明
Thioacetamide occurs as a colorless leaf-like material with aslight Sulfur-like odor. It is used as a substitute for HydrogenSulfide in the laboratory and as a stabilizer of motor fuel.
使用用途
チオアセトアミドの主な用途は、染料、医薬品および医薬品中間体、合成中間体、写真・印刷薬品です。例えば、カドミウムイオンの溶液にチオアセトアミド水溶液を加えた後に加温することで、硫化カドミウムが得られます。この硫化カドミウムは、黄色顔料であるカドミウムイエローの主成分です。 このほか、チオアセトアミドは、古典的定性分析におけるの供給源であり、金属硫化物の沈殿試薬 (均質沈殿法) 、金属イオンの系統分析の分属試薬に使用されています。
製法・合成法
合成方法
酢酸アンモニウムと硫化アルミニウムとの反応や，アセトニトリルと硫化水素との反応，またはアセトアミドの硫化反応で得られる
純化方法
Crystallise the amide from absolute diethyl ether or *benzene. Dry it at 70o in a vacuum and store it over P2O5 at 0o under nitrogen. (It develops an obnoxious odour on storage, and absorption at 269nm decreases, hence it should be freshly recrystallised before use). [Beilstein 2 IV 565.]