HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzothiazole
Benzo[d]thiazole · Benzothiazol · FEMA 3256 · 1,3-BENZOTHIAZOLE · Benzthiazole · Benzosulfonazole · Vangard BT · 5-Benzothiazole boronic acid pinacol ester
Identifiers & Physical Properties
| CAS No. | 95-16-9 |
|---|---|
| Molecular formula | C7H5NS |
| Average molar mass | 135.19 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 2 |
|---|---|
| Topological polar surface area | 41.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 105 |
| LogP (partition coefficient) | 2.01 |
| Odor | ODOR SIMILAR TO THAT OF QUINOLINEUnpleasant odorodor of quinoline, sltly water-sol |
| Density | 1.246 AT 20 °C/4 °C1.236-1.2401.238 @25 °C1.238 g/mL at 25 °C (lit.) |
| Color/Form | Yellow liquid |
| Solubility | 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/l |
| Boiling point | 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/ |
| Melting point | 2 °C2 °C (lit.) |
| Odor threshold | Odor Threshold Low: 0.08 [ppm]Odor Threshold High: 0.4 [ppm]Odor threshold from CHEMINFO |
| Vapor pressure | 0.01 [mmHg]34 mm Hg ( 131 °C) |
| Refractive index | 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 |
| Vapor density | 4.66 (vs air) |
| FEMA | 3256 | BENZOTHIAZOLE |
| FLAVIS Number | 15.016 | Benzothiazole |
| Flash point | >230 °F |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (acidity coefficient) | 0.85±0.10(Predicted) |
| Physical state | Liquid |
| Color | Clear yellow-brown to brown |
| Odor type | sulfurous |
| Biological source | synthetic |
| Explosive limits | 0.9-8.2%(V) |
| JECFA Number | 1040 |
| Merck | 14,1107 |
| BRN | 109468 |
| Henry's law constant | 2.7×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stability | Stable - regarded as highly persistent in the environment. Incompatible with strong oxidizing agents. Combustion products: nitrogen oxides, carbon monoxide, carbon dioxide, sulphur oxides. |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H |
| InChIKey | IOJUPLGTWVMSFF-UHFFFAOYSA-N |
| SMILES | c1ccc2scnc2c1 |
| LogP (partition coefficient) | 2.01 |
| CAS DataBase Reference | 95-16-9(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | BENZOTHIAZOLE |
| EWG's Food Scores | 1 |
| FDA UNII | G5BW2593EP |
| NIST Chemistry Reference | Benzothiazole(95-16-9) |
| EPA Substance Registry System | Benzothiazole (95-16-9) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS06 |
| Signal word | Danger |
| GHS hazard statements | H301+H311-H319 |
| GHS precautionary statements | P264-P270-P280-P301+P310-P302+P352+P312-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn,T,Xi |
| Risk statements (R) | 22-20/21/22-36-25-24-20 |
| Safety statements (S) | 23-26-36-36/37-45 |
| UN transport number | 2810 |
| Water hazard class (WGK) | 2 |
| RTECS number | DL0875000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2 |
| Packing group | III |
| Customs code | 29342080 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazardous substances data | 95-16-9(Hazardous Substances Data) |
| Toxicity | LD50 i.v. in mice: 95±3 mg/kg (Domino) |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | 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] |
|---|---|
| Regulatory information | 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 |
| Hazards summary | 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/ |
| Disposal methods | 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] |
| Environmental fate | 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 | 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 effects | 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). |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | DL0875000 |
| UN transport number | 2810 |
| Customs code | 29342080 |
| Toxicity | LD50 i.v. in mice: 95±3 mg/kg (Domino) |
| Risk statements (R) | 22-20/21/22-36-25-24-20 |
| Signal word | Danger |
| GHS pictogram | GHS06 |
| Hazard symbols | Xn,T,Xi |
| Safety statements (S) | 23-26-36-36/37-45 |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Packing group | III |
| GHS hazard statements | H301+H311-H319 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| GHS precautionary statements | P264-P270-P280-P301+P310-P302+P352+P312-P305+P351+P338 |
| Hazardous substances data | 95-16-9(Hazardous Substances Data) |
Applications & Uses
Description
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.
Occurrence
Reported found in apricot, cooked asparagus, mozzarella cheese, skim milk powder, roasted beef, beer, malt whiskey, coconut meat, fresh mango, cooked broccoli and kelp.
Uses
Various benzothiazole-benzamides synthesized were evaluated for their analgesic and antidepressant activities.
Uses
It is an interesting carbonyl equivalent and reacts with aldehydes or ketones to generate α-hydroxy carbonyl compounds. Benzothiazole is used as a chemical intermediate in organic synthesis. It is a precursor of rubber accelerators and a component of cyanine dyes. It is also used as a flavoring substance. It is also used as a flavor, antimicrobial agent, and component of cyanine dyes. Its derivatives are used as rubber accelerators.
General Description
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.
Preparation & Synthesis
Preparation
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.