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ベンゾチアゾール

Benzothiazole

HCID 7222
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
95-16-9
標準SMILES
c1ccc2scnc2c1
InChIKey
IOJUPLGTWVMSFF-UHFFFAOYSA-N
分子式
C7H5NS
平均分子量
135.19 g/mol
単同位体質量
135.01427034

概要

Benzothiazole is an organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles. It has a role as a xenobiotic, a plant metabolite and an environmental contaminant.

名称と識別子

優先名称
Benzothiazole
IUPAC
1,3-benzothiazole
現地名
ベンゾチアゾール
英語名
Benzothiazole
分子式
C7H5NS
分子量
135.19

名称と別名

BENZOTHIAZOLE95-16-91,3-BenzothiazoleBenzosulfonazole1-Thia-3-azaindeneVangard BTUSAF EK-4812FEMA Number 3256FEMA No. 3256DTXSID7024586O-2857CHEBI:45993
名称をさらに表示
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FEMA 32565-Benzothiazole boronic acid pinacol esterNSC 8040
G5BW2593EPNSC-8040DTXCID204586RefChem:118563202-396-2BENZO[D]THIAZOLEbenzothiazolbenzthiazole

データベース識別子

CAS
95-16-9
PubChem CID
7222
DTXSID
DTXSID7024586
ChEMBL
CHEMBL510309
ChEBI
CHEBI:45993
UNII
G5BW2593EP
EC Number
202-396-2
Nikkaji
J40.177C

物性

構造計算による物性補完中

XLogP
2
極性表面積
41.1 Ų
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

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Thiazoles
PolymersRubber
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Benzothiazole) -> IFRA transparency List
LogP · 2 件

2.01

2.03

Odor · 2 件

ODOR SIMILAR TO THAT OF QUINOLINE

Unpleasant odor

Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 3 件

1.246 AT 20 °C/4 °C

1.236-1.240

1.238 @25 °C

Flavoring AgentsEU Flavoring substances
Color/FormYellow liquid
Solubility · 5 件

SLIGHTLY SOL IN WATER; SOL IN ALC, CARBON DISULFIDE

Very soluble in ether, soluble in acetone, slightly soluble in water.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H301+H311 (10.2%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

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.

H402: Harmful to aquatic life [Hazardous to the aquatic environment, acute hazard]

P273, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: Benzothiazole

Regulation (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)

REACH registered substance: Benzothiazole (EC: 202-396-2)

Benzothiazole: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Not irritating to skin, but irritating to eyes of rabbits; Lethal-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 irritant; Causes 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 · 5 件

Drzyga O et al; Appl Environ Microbiol 62 (5): 1710-16 (1996). Cometabolic transformation and cleavage of nitrodiphenylamines by three newly isolated sulfate reducing bacterial strains.

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

Uses · 5 件

Used as a flavor, antimicrobial agent, and component of cyanine dyes; Derivatives used as rubber accelerators; [HSDB] Used in organic synthesis; [Merck Index]

FLAVORING SUBSTANCE OR ADJUVANT

RUBBER ACCELERATOR /THIAZOLES/

ANTIMICROBIAL AGENT

Component of cyanine dyes

U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
U.S. Production · 2 件

2023: 250,000 - <550,000 lb

(1986) No Data

Consumer UsesProcessing aids not otherwise specified
Industry UsesProcessing aids not otherwise specified
Methods of Manufacturing · 2 件

PREPD FROM N,N-DIMETHYLANILINE & SULFUR: KNOWLES, WATT, J ORG CHEM 7, 56 (1942).

BY REFLUXING MIXT OF ZINC O-AMINOPHENYLSULFIDE & FORMIC ACID, FOLLOWED BY STEAM DISTILLATION OF ALKALIZED REACTION MIXT...BY HEATING FORMANILID OR DIMETHYLANILINE WITH SULFUR...BY OXIDATION OF 2-MERCAPTOBENZOTHIAZOLE OR OF CORRESPONDING DISULFIDE...

Use Classification · 3 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 6 件

Rubber Product Manufacturing

Benzothiazole: ACTIVE

REPORTED USES: NON-ALCOHOLIC BEVERAGES, CANDY, BAKED GOODS, MEAT, MEAT SAUCES, SOUPS, MILK, DAIRY PRODUCTS ALL 0.5 PPM. /FROM TABLE/

関連反応

146 件
反応記録を作成
HRID 33756 の反応式
HRID 33756生成物としてuspto-grants-2008_09
HRID 66595 の反応式
HRID 66595反応物としてuspto-grants-1982_08
HRID 110697 の反応式
HRID 110697生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 126964 の反応式
HRID 126964反応物としてuspto-grants-1981_03
HRID 138707 の反応式
HRID 138707反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 139946 の反応式
HRID 139946反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 169896 の反応式
HRID 169896生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 178957 の反応式
HRID 178957反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
1 / 19 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す

4.3 mg/mL at 25 °C

Very slightly soluble in water; Soluble in acetone, carbon disulfide

Miscible at room temperature (in ethanol)

Boiling Point · 4 件

227-228 °C AT 765 MM HG

231.00 to 233.00 °C. @ 760.00 mm Hg

231 °C

231 °C @760 [mm Hg]

物理化学的性質

融点
2 °C · 2 °C (lit.)
沸点
231 °C · 231 °C (lit.)
比重(密度)
1.238 g/mL · 1.238 g/mL at 25 °C (lit.)
蒸気密度
4.66 · 4.66 (vs air)
蒸気圧
34 mm · 34 mm Hg ( 131 °C)
屈折率
20 · n20/D 1.642(lit.)
FEMA
3256 · 3256 | BENZOTHIAZOLE
闪点
230 °F · >230 °F
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
溶解性
3 g/リットル · 3g/リットル
酸解離定数(Pka)
0.85 · 0.85±0.10(Predicted)
外見
液体
色
澄んだ黄褐色~褐色
臭い (Odor)
キノリンのにおい、少し水っぽい
においのタイプ
硫黄の
由来生物
synthetic
爆発限界(explosive limit)
0.9 · 0.9-8.2%(V)
水溶解度
わずかに溶ける
JECFA Number
1040 · 1040
Merck
14 · 14,1107
BRN
109468 · 109468
Henry's Law Constant
2.7 · 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
2.01 · 2.01
CAS データベース
95 · 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)

化学的性質

化学的特性Benzothiazole has a delicate, persistent, rose-like odor similar to that of quinoline.

Paxeus N; Water Res 30 (5): 1115-22 (1996). Organic pollutants in the effluents of large wastewater treatment plants in Sweden.

Puig A et al; J Chromatog 733 (1-2): 511-22 (1996). Wastewater from the manufacture of rubber vulcanization accelerators: Characterization, downstream monitoring and chemical treatment.

Scott BF et al; Water 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 · 3 件

Acute Tox. 3 (88.2%)

Acute toxicity (Oral) - Category 4

Hazardous to the aquatic environment (Acute) - Category 3

Hazardous Reactivities and Incompatibilities · 2 件

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/

安全と保護具

Disposal Methods · 1 件

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) · 3 件

1.1 [mg/m3]

13 [mg/m3]

75 [mg/m3]

毒性情報

Toxicological InformationRanking: 562 (total points: 173.21)
Environmental Fate · 3 件

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).

Food Survey Values · 1 件

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).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Plant ConcentrationsUnspecified 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 ConcentrationsUnspecified amounts of benzothiazole were identified in the shells of gastropod molluscs in Australia(1,2).
Effluent Concentrations · 2 件

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 · 1 件

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 ConcentrationsUnspecified amounts of benzothiazole were detected in clams from Japan(1).
Artificial Pollution Sources · 1 件

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 · 1 件

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 · 1 件

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).

安全データ

wgk
2
tsca
TSCA listed
rtecs
DL0875000
ridadr
2810
毒性
LD50 i.v. in mice: 95±3 mg/kg (Domino)
hs_code
29342080
risk_code
22-20/21/22-36-25-24-20
化審法
(5)-3426
消防法
危-4-3-III
hazard_code
Xn,T,Xi
safety_code
23-26-36-36/37-45
hazard_class
6.1
packing_group
III
環境リスク評価
ベンゾチアゾール(95-16-9)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
95-16-9(Hazardous Substances Data)

BENZOTHIAZOLE IS USED TO PREVENT MICROBIAL GROWTH IN SHOES & ATHLETES FOOT DEVELOPMENT. POROUS INSOLES ARE IMPREGNATED WITH SOLN CONTAINING BENZOTHIAZOLE.

...IN...COCOA, SHALLOW-FRIED BEEF, SOYBEAN MILK, STORED CASEIN, HEATED MILK, STALE NON-FAT DRY MILK, & STERILIZED CONCENTRATED MILK...ONLY THIAZOLE DERIV REPORTED WAS BENZOTHIAZOLE.

...BENZOTHIAZOLE /WAS REPORTED/ TO BE PRESENT IN BEER.

応用分野 · 6 件

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.

調製方法 · 1 件

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.

上流・下流製品情報

上流原料

亜鉛スルフィドN-メチルアニリン2-メルカプトベンゾチアゾール硝酸アンモニウム二硫化モリブデンN,N-ジメチルアニリン2-(METHYLSULFONYL)BENZOTHIAZOLE, 97メタンスルフィン酸ナトリウム

下流製品

プラミペキソール6-ベンゾチアゾールアミンDirect Fast Yellow RR2-[4-[[1-[[(2-メトキシフェニル)アミノ]カルボニル]-2-オキソプロピル]アゾ]-3-スルホフェニル]-6-メチル-7-ベンゾチアゾールスルホン酸二ナトリウムBasic Yellow 242-アミノフェニルフェニルスルフィド2-ベンゾチアゾールカルボン酸ベンゾチアゾリン2-ヨードベンゾチアゾール2-(2-ヒドロキシフェニル)ベンゾチアゾール2-アミノ-6-ニトロベンゾチアゾール2-(メチルチオ)ベンゾチアゾール

補足説明

定義ChEBI: An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.