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ベンゾチアゾール
ベンゾチアゾール · ベンゾスルホナゾール · ベンゾチアゾ-ル · ベンゾチアゾル · 1,3-ベンゾチアゾール · ベンゾ[D]チアゾール · Benzo[d]thiazole · Benzothiazol
識別子と物理属性
| CAS No. | 95-16-9 |
|---|---|
| 分子式 | C7H5NS |
| 平均分子量 | 135.19 g/mol |
| 単同位体質量 | 135.01427034 g/mol |
| SMILES | c1ccc2scnc2c1 |
| InChIKey | IOJUPLGTWVMSFF-UHFFFAOYSA-N |
| PubChem CID | 7222 |
| ChEMBL | CHEMBL510309 |
| ChEBI | CHEBI:45993 |
| EC No. | 202-396-2 |
| DTXSID | DTXSID7024586 |
| 現地名 | ベンゾチアゾール |
化学・物理的性質
| XLogP | 2 |
|---|---|
| 極性表面積 | 41.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 105 |
| LogP（分配係数） | 2.01 |
| 臭い | ODOR SIMILAR TO THAT OF QUINOLINEUnpleasant odorキノリンのにおい、少し水っぽい |
| 密度 | 1.246 AT 20 °C/4 °C1.236-1.2401.238 @25 °C1.238 g/mL at 25 °C (lit.) |
| Color/Form | Yellow liquid |
| 溶解度 | SLIGHTLY SOL IN WATERSOL IN ALC, CARBON DISULFIDEVery soluble in ether, soluble in acetone, slightly soluble in water.4.3 mg/mL at 25 °CVery slightly soluble in waterSoluble in acetone, carbon disulfideMiscible at room temperature (in ethanol)3g/リットルわずかに溶ける |
| 沸点 | 227-228 °C AT 765 MM HG231.00 to 233.00 °C. @ 760.00 mm Hg231 °C231 °C @760 [mm Hg]231 °C (lit.) |
| Decomposition | WHEN HEATED TO DECOMP, THEY EMIT HIGHLY TOXIC FUMES OF SO(X)/SULFIDES/ |
| 融点 | 2 °C2 °C (lit.) |
| 臭気閾値 | Odor Threshold Low: 0.08 [ppm]Odor Threshold High: 0.4 [ppm]Odor threshold from CHEMINFO |
| 蒸気圧 | 0.01 [mmHg]34 mm Hg ( 131 °C) |
| 屈折率 | INDEX OF REFRACTION: 1.6379 AT 20 °C/D1.637-1.644n20/D 1.642(lit.) |
| Physical Description | LiquidYellow liquid with an unpleasant odormp = 2 deg C[HSDB] Colorless liquid[Alfa Aesar MSDS]Clear to amber liquidquinoline-like, rubbery odour |
| 蒸気密度 | 4.66 (vs air) |
| FEMA | 3256 | BENZOTHIAZOLE |
| 引火点 | >230 °F |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Room temperature |
| pKa（酸解離定数） | 0.85±0.10(Predicted) |
| 外観・状態 | 液体 |
| 色 | 澄んだ黄褐色～褐色 |
| においのタイプ | 硫黄の |
| 由来生物 | synthetic |
| 爆発限界 | 0.9-8.2%(V) |
| JECFA Number | 1040 |
| Merck | 14,1107 |
| BRN | 109468 |
| ヘンリー定数 | 2.7×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定 - 環境内で持続性が高いと考えられています。強力な酸化剤とは相容れない。燃焼生成物：窒素酸化物、一酸化炭素、二酸化炭素、硫黄酸化物。 |
| 化粧品成分の機能 | 香料 |
| InChI | 1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H |
| InChIKey | IOJUPLGTWVMSFF-UHFFFAOYSA-N |
| SMILES | c1ccc2scnc2c1 |
| LogP（分配係数） | 2.01 |
| CAS データベース | 95-16-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzothiazole(95-16-9) |
| EPAの化学物質情報 | Benzothiazole (95-16-9) |
化学的特性
Benzothiazole has a delicate, persistent, rose-like odor similar to that of quinoline.
安全性と法規制
| GHS 分類 | DangerH301+H311 (10.2%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oralacute toxicity, dermal]H301 (88.2%): Toxic if swallowed [Danger Acute toxicity, oral]H302 (11.8%): Harmful if swallowed [Warning Acute toxicity, oral]H311 (88.3%): Toxic in contact with skin [Danger Acute toxicity, dermal]H319 (88.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (88.2%): Harmful if inhaled [Warning Acute toxicity, inhalation]P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P321, P330, P337+P317, P361+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1775 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.H402: Harmful to aquatic life [Hazardous to the aquatic environment, acute hazard]H412: Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard] |
|---|---|
| 規制情報 | Chemical: BenzothiazoleRegulation (EC) No 1831/2003 (amended)Benzothiazole is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzothiazole 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: 28-07-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/13176Benzothiazole: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Not irritating to skin, but irritating to eyes of rabbitsLethal-dose gavage study of cats produced mild methemoglobinemia and Heinz bodies in up to 100% of erythrocytes[IUCLID] Safe when used as a flavoring agent in food[JECFA] A mild skin and eye irritantCauses pulmonary emboli and other changes to liver in dermal lethal-dose study of rabbits and oral lethal-dose study of rats[RTECS] A mild skin and strong eye irritant[Alfa Aesar MSDS] |
| Special Reports | Drzyga O et alAppl Environ Microbiol 62 (5): 1710-16 (1996). Cometabolic transformation and cleavage of nitrodiphenylamines by three newly isolated sulfate reducing bacterial strains.Paxeus NWater Res 30 (5): 1115-22 (1996). Organic pollutants in the effluents of large wastewater treatment plants in Sweden.Puig A et alJ Chromatog 733 (1-2): 511-22 (1996). Wastewater from the manufacture of rubber vulcanization accelerators: Characterization, downstream monitoring and chemical treatment.Scott BF et alWater Qual Res J Canada 31 (2): 341-60 (1996). Determination of benzothiazole and alkylphosphates in water samples from the Great Lakes drainage basin.For more Special Reports (Complete) data for BENZOTHIAZOLE (10 total), please visit the HSDB record page. |
| Hazard Classes and Categories | Acute Tox. 3 (88.2%)Acute Tox. 4 (11.8%)Acute Tox. 3 (88.3%)Eye Irrit. 2 (88.3%)Acute Tox. 4 (88.2%)Acute toxicity (Oral) - Category 4Acute toxicity (Dermal) - Category 2Skin corrosion/irritation - Category 3Serious eye damage/eye irritation - Category 2BHazardous to the aquatic environment (Acute) - Category 3Hazardous to the aquatic environment (Long-term) - Category 3 |
| Hazardous Reactivities and Incompatibilities | REACT WITH WATER, STEAM OR ACIDS TO PRODUCE TOXIC & FLAMMABLE VAPORS OF HYDROGEN SULFIDE. /SULFIDES/ON CONTACT WITH ACID, ACID FUMES, WATER OR STEAM, THEY WILL PRODUCE TOXIC & FLAMMABLE VAPORS. /CYANIDES/ |
| 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. |
| Protective Action Criteria (PAC) | 1.1 [mg/m3]13 [mg/m3]75 [mg/m3] |
| 環境中動態 | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 295(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that benzothiazole will have moderate mobility in soil(SRC). Volatilization of benzothiazole will not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.7X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Biodegradation of benzothiazole occurs rapidly under aerobic conditions. Employing a standard BOD dilution technique and an activated sludge inoculum, a theoretical BOD of 100% was observed for a 0.0125 mM sample of benzothiazole over an unspecified time period(5). Unspecified concentrations of benzothiazole were degraded by both mixed cultures and activated sludge mediums(6).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 295(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(1), indicates that benzothiazole may adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces should be slow based upon an estimated Henry's law constant of 3.7X10-7 atm-cu m/mol (SRC), developed using a fragment constant estimation method(3). Estimated half-lives for a model river and model lake are 114 and 832 days, respectively(1,SRC). According to a classification scheme(4), an estimated BCF value of 20(1,SRC), from an experimental log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). The biodegradation of benzothiazole occurs rapidly under aerobic conditions. Complete biodegradation of 72X10-6 mols/l of benzothiazole incorporated into an activated sludge medium obtained from a municipal wastewater treatment facility was observed after a period of 16 days(5).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzothiazole, which has an estimated vapor pressure of 0.014 mm Hg at 25 °C(2,SRC), will exist solely as a vapor in the ambient atmosphere. Benzothiazole 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 18 hours(3,SRC). |
| 食品調査値 | Quantities of benzothiazole were found in salt fermented anchovies and hair tail viscera shrimp at concentrations of 124 ng/g and 247 ng/g respectively(1). Unspecified amounts of benzothiazole were detected in samples of cassava roots from the Dominican Republic(2), nectarines from California(3), apples from Kogyoku, Japan(4) and volatiles of roasted filbert nuts(5). |
| 有害作用 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Plant Concentrations | Unspecified amounts of benzothiazole were detected in samples of cassava roots originating from the Dominican Republic(1) and plant materials in Fulton county, Illinois(2). |
| Animal Concentrations | Unspecified amounts of benzothiazole were identified in the shells of gastropod molluscs in Australia(1,2). |
| Effluent Concentrations | ONE OF 2 TIRE PLANTS STUDIED FOR TRACE ORGANIC COMPDS IN WASTE WATERS RECYCLES ANTI-TACK SOLN & EMITS MOSTLY BENZOTHIAZOLE & 2-MERCAPTOBENZOTHIAZOLE.Benzothiazole was detected in effluents of German incinerator plants at concentrations of about 3.1X10-7 g/cu m (1). Unspecified concentrations of benzothiazole were detected in pyrolytic oil waste streams in Winchester, Virginia following a fire at a tire storage facility(2). Unspecified concentrations of benzothiazole were detected in effluents from rubber vulcanization manufacturing facilities(3,4). Concentrations of 2 ppb were detected in wastewater streams in the vicinity of a specialty chemical manufacturing plant whose location was not specified(5). Benzothiazole was detected in tire manufacturing plant wastewater streams at unspecified locations at concentrations of 20-60 ppb(6). |
| Soil Adsorption/Mobility | The Koc of benzothiazole is estimated as approximately 295(SRC), using an experimental log Kow of 2.01(1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that benzothiazole has moderate mobility in soil(SRC). |
| Fish/Seafood Concentrations | Unspecified amounts of benzothiazole were detected in clams from Japan(1). |
| Artificial Pollution Sources | Benzothiazole's production and use as a synthetic reagent in organic chemistry(1) may result in its release to the environment through various waste streams(SRC). The degradation of fungicides containing 2-(thiocyanomethylthio)benzothiazole and the rubber vulcanization agent, 2-mercaptobenzothiazole results in the formation of benzothiazole(2). |
| Environmental Biodegradation | Complete biodegradation of 72X10-6 mols/l of benzothiazole incorporated into an activated sludge medium obtained from a municipal wastewater treatment facility was observed after 16 days (1). Employing a standard BOD dilution technique and an activated sludge inoculum, a theoretical BOD of 100% was observed for a 0.0125 mM sample of benzothiazole over an unspecified time period, while a 0.125 mM sample produced a theoretical BOD of 10%(2). An activated sludge innoculum biodegraded benzothiozaole over a 6 month incubation period(3). This data would suggest that low levels of benzothiazole are totally biodegraded, while high concentrations are expected to be toxic to microbes(SRC). |
| Environmental Bioconcentration | An estimated BCF value of 20 was calculated for benzothiazole(SRC), using an experimental log Kow of 2.01(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for benzothiazole is estimated as 3.7 X 10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that benzothiazole will volatilize slowly 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 114 days(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 832 days(2,SRC). Benzothiazole's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces should be slow(SRC). |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DL0875000 |
| 輸送番号（UN） | 2810 |
| 毒性 | LD50 i.v. in mice: 95±3 mg/kg (Domino) |
| 税関コード | 29342080 |
| 危険文句（R） | 22-20/21/22-36-25-24-20 |
| 化審法 | (5)-3426 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xn,T,Xi |
| 安全措置（S） | 23-26-36-36/37-45 |
| 危険等級 | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2 |
| 包装等級 | III |
| 環境リスク評価 | ベンゾチアゾール(95-16-9) |
| 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 | 95-16-9(Hazardous Substances Data) |
用途
解説
C7H5NS(135.18)．ベンゾチアゾールは，N,N-ジメチルアニリンと硫黄とを加熱するか，o-アミノチオフェノールとホルマリンとの反応で得られる．キノリン臭のある液体で，水蒸気蒸留される．沸点227～228 ℃，131 ℃(4.5 kPa)．d2041.246．n20D1.6379．エタノール，二硫化炭素に易溶，水に難溶．中性を示す．五塩化リンを作用させると2-クロル誘導体を，混酸でニトロ化すれば6-ニトロ誘導体を与える．森北出版「化学辞典（第2版）
用途
有機合成原料。
説明
Benzothiazole and its derivative are recognized as the most important heterocyclic compounds. This series of compounds is of particular interests. It has various kinds of pharmacological properties and has been included in many kinds of natural products and pharmaceutical agents. The broad spectrum of pharmacological activity in individual benzothiazole derivative enables it to serve as unique and valuable scaffolds for experimental drug design. It is already known that benzothiazole and its derivative has various biological applications including anticancer, antimicrobial, anticonvulsant, antiviral, antidiabetic, antipsychotic, antiinflammatory, analgesic, fungicidal and diuretic. Its derivatives also have many applications in polymer chemistry, dyes, drugs, and silver photography as well as rubber industry.
天然物の起源
Reported found in apricot, cooked asparagus, mozzarella cheese, skim milk powder, roasted beef, beer, malt whiskey, coconut meat, fresh mango, cooked broccoli and kelp.
使用
Various benzothiazole-benzamides synthesized were evaluated for their analgesic and antidepressant activities.
一般的な説明
Benzothiazole, a volatile sulfur-containing heterocyclic compound, is one of the key odorants of heated milk. It is also reported to occur as a flavor component of miso, coconut meat and cooked-beef.
製法・合成法
製造方法
By refluxing a mixture of zinc o-aminophenylsulfide and formic acid, followed by steam distillation of the alkalized reaction mixture; by heating formanilid or dimethylaniline with sulfur; by oxidation of 2-mercaptobenzothiazole or of the corresponding disulfide.