StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Verbindung

Benzothiazol

Benzothiazole

HCID 7222
Neue NotizNeue ReaktionAnfrage stellen
Druckvorschau
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
95-16-9
Standard-SMILES
c1ccc2scnc2c1
InChIKey
IOJUPLGTWVMSFF-UHFFFAOYSA-N
Summenformel
C7H5NS
Durchschnittliche Molmasse
135,19 g/mol
Monoisotopische Masse
135,01427034

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Benzothiazole
IUPAC
1,3-benzothiazole
Lokaler Name
Benzothiazol
Englischer Name
Benzothiazole
Summenformel
C7H5NS
Molmasse
135.19

Namen und Synonyme

BENZOTHIAZOLE95-16-91,3-BenzothiazoleBenzosulfonazole1-Thia-3-azaindeneVangard BTUSAF EK-4812FEMA Number 3256FEMA No. 3256DTXSID7024586O-2857CHEBI:45993
Weitere Namen anzeigen
FEMA 32565-Benzothiazole boronic acid pinacol esterNSC 8040
G5BW2593EPNSC-8040DTXCID204586RefChem:118563202-396-2BENZO[D]THIAZOLEbenzothiazolbenzthiazole

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2
Polarare Oberfläche (TPSA)
41,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
9
Formalladung
0
Komplexität
105

Experimentelle und physikochemische Eigenschaften

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

2.01

2.03

Odor · 2 Einträge

ODOR SIMILAR TO THAT OF QUINOLINE

Unpleasant odor

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

1.246 AT 20 °C/4 °C

1.236-1.240

1.238 @25 °C

Flavoring AgentsEU Flavoring substances
Color/FormYellow liquid

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Gefahrenhinweise

Regulatory Information · 5 Einträge

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 Eintrag

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 Einträge

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 5 Einträge

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 Einträge

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 Einträge

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 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 6 Einträge

Rubber Product Manufacturing

Zugehörige Reaktionen

146
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 33756
HRID 33756als Produktuspto-grants-2008_09
Reaktionsgleichung von HRID 66595
HRID 66595als Eduktuspto-grants-1982_08
Reaktionsgleichung von HRID 110697
HRID 110697als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 126964
HRID 126964als Eduktuspto-grants-1981_03
Reaktionsgleichung von HRID 138707
HRID 138707als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 139946
HRID 139946als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 169896
HRID 169896als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 178957
HRID 178957als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Seite 1 von 19

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
Solubility · 5 Einträge

SLIGHTLY SOL IN WATER; SOL IN ALC, CARBON DISULFIDE

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

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 Einträge

227-228 °C AT 765 MM HG

231.00 to 233.00 °C. @ 760.00 mm Hg

231 °C

231 °C @760 [mm Hg]

Physikochemische Eigenschaften

Schmelzpunkt
2 °C · 2 °C (36 °F; 275 K)
Siedepunkt
227 to · 227 to 228 °C (441 to 442 °F; 500 to 501 K)
Dichte
1.238 g/mL · 1.238 g/mL
Dampfdichte
4.66 · 4.66 (vs air)
Dampfdruck
34 mm · 34 mm Hg ( 131 °C)
FEMA
3256 · 3256 | BENZOTHIAZOLE
Brechungsindex
1.64 · 1.64
Flammpunkt
107 °C · 107 °C
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
3 g/l · 3g/l
pka
0.85 · 0.85±0.10(Predicted)
Aggregatzustand
liquid
Farbe
colorless
Geruch (Odor)
odor of quinoline, sltly water-sol
Explosionsgrenze
0.9 · 0.9-8.2%(V)
Geruchsart
sulfurous
Biologische Quelle
synthetic
Wasserlöslichkeit
slightly soluble
Merck
14 · 14,1107
JECFA Number
1040 · 1040
BRN
109468 · 109468
Henry's Law Constant
2.7 · 2.7×101 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Stable - regarded as highly persistent in the environment. Incompatible with strong oxidizing agents. Combustion products: nitrogen oxides, carbon monoxide, carbon dioxide, sulphur oxides.
Kosmetik-Inhaltsstoffe Funktionen
PERFUMING
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 Datenbank
95 · 95-16-9(CAS DataBase Reference)
NIST chemische Informationen
Benzothiazole(95-16-9)
EPA chemische Informationen
Benzothiazole (95-16-9)

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.

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 Einträge

Acute Tox. 3 (88.2%)

Acute toxicity (Oral) - Category 4

Hazardous to the aquatic environment (Acute) - Category 3

Hazardous Reactivities and Incompatibilities · 2 Einträge

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/

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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 Einträge

1.1 [mg/m3]

13 [mg/m3]

75 [mg/m3]

Toxikologische Informationen

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

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 Eintrag

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 Einträge

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 Eintrag

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 Eintrag

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 Eintrag

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 Eintrag

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).

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
2810
hs_code
2934200090
RTECS-Nr.
DL0875000
risk_code
22-20/21/22-36-25-24-20
Toxizität
LD50 i.v. in mice: 95±3 mg/kg (Domino)
hazard_code
Xn,T,Xi
safety_code
23-26-36-36/37-45
hazard_class
6.1
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
95-16-9(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2

Benzothiazole: ACTIVE

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

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.

Anwendungen · 4 Einträge

BeschreibungStibinobenzol bildet ein gelbes, wasserunlösliches, an der Luft sehr oxidables Pulver. Manchmal verläuft die Oxidation so lebhaft, daß die Substanz Feuer fängt. Konzentrierte Salpetersäure bewirkt explosionsartige Zersetzung. Stibinobenzol hat keinen defi

BeschreibungBenzothiazole 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.

OccurrenceReported found in apricot, cooked asparagus, mozzarella cheese, skim milk powder, roasted beef, beer, malt whiskey, coconut meat, fresh mango, cooked broccoli and kelp.

VerwendenVarious benzothiazole-benzamides synthesized were evaluated for their analgesic and antidepressant activities.

Darstellung · 1 Eintrag

synthetischeBy 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

ZinksulfidN-Methyl-anilinBenzothiazol-2-thiolAmmoniumnitratMolybdaendisulfidN,N-Dimethyl-anilin2-(Methylsulfonyl)benzothiazole, 97Natriummethansulfinat

Nachgelagerte Produkte

PramipexoleBenzothiazol-6-aminDirect Fast Yellow RRDinatrium-2-[4-[[1-[[(2-methoxyphenyl)amino]carbonyl]-2-oxopropyl]azo]-3-sulfonatophenyl]-6-methylbenzothiazol-7-sulfonat2-[[(1,3-Dihydro-1,3-dimethyl-2H-benzimidazol-2-yliden)methyl]azo]-3-methylbenzothiazoliummethylsulfat2-(Phenylthio)anilineBenzothiazole-2-carboxylic acidbenzothiazoline2-Iodobenzothiazole2-Benzothiazol-2-ylphenol6-Nitrobenzothiazol-2-amin2-(Methylthio)benzothiazol

Ergänzende Hinweise

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