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Benzothiazole

HCID 7222
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
95-16-9
Standard SMILES
c1ccc2scnc2c1
InChIKey
IOJUPLGTWVMSFF-UHFFFAOYSA-N
Molecular formula
C7H5NS
Average molar mass
135.19 g/mol
Monoisotopic mass
135.01427034

Overview

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.

Names & identifiers

Preferred name
Benzothiazole
IUPAC
1,3-benzothiazole
English name
Benzothiazole
Molecular formula
C7H5NS
Molecular weight
135.19

Names & synonyms

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

Database identifiers

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

Properties

Computed structural propertiesFilling in

XLogP
2
Topological polar surface area
41.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
9
Formal charge
0
Complexity
105

Experimental & physicochemical properties

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

2.01

2.03

Odor · 2 items

ODOR SIMILAR TO THAT OF QUINOLINE

Unpleasant odor

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

1.246 AT 20 °C/4 °C

1.236-1.240

1.238 @25 °C

Flavoring AgentsEU Flavoring substances
Color/FormYellow liquid

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 5 items

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 item

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 items

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.

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 5 items

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 items

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 items

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 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 6 items

Rubber Product Manufacturing

Benzothiazole: ACTIVE

Related reactions

146 records
New reaction record
HRID 33756 reaction equation
HRID 33756As productuspto-grants-2008_09
HRID 66595 reaction equation
HRID 66595As reactantuspto-grants-1982_08
HRID 110697 reaction equation
HRID 110697As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 126964 reaction equation
HRID 126964As reactantuspto-grants-1981_03
HRID 138707 reaction equation
HRID 138707As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 139946 reaction equation
HRID 139946As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 169896 reaction equation
HRID 169896As productTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 178957 reaction equation
HRID 178957As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
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Compound notes

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Solubility · 5 items

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 items

227-228 °C AT 765 MM HG

231.00 to 233.00 °C. @ 760.00 mm Hg

231 °C

231 °C @760 [mm Hg]

Physicochemical properties

Melting point
2 °C · 2 °C (lit.)
Boiling point
231 °C · 231 °C (lit.)
Density
1.238 g/mL · 1.238 g/mL at 25 °C (lit.)
vapor density
4.66 · 4.66 (vs air)
vapor pressure
34 mm · 34 mm Hg ( 131 °C)
refractive index
20 · n20/D 1.642(lit.)
FEMA
3256 · 3256 | BENZOTHIAZOLE
FLAVIS Number
15.016 · 15.016 | Benzothiazole
Flash point
230 °F · >230 °F
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
3 g/l · 3g/l
pka
0.85 · 0.85±0.10(Predicted)
form
Liquid
color
Clear yellow-brown to brown
Odor
odor of quinoline, sltly water-sol
Odor Type
sulfurous
biological source
synthetic
explosive limit
0.9 · 0.9-8.2%(V)
Water Solubility
slightly soluble
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)
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
2.01 · 2.01
CAS DataBase Reference
95 · 95-16-9(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
BENZOTHIAZOLE
EWG's Food Scores
1 · 1
FDA UNII
5 BW2593EP · G5BW2593EP
NIST Chemistry Reference
Benzothiazole(95-16-9)
EPA Substance Registry System
Benzothiazole (95-16-9)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301+H311-H319
Precautionary statements
264 · P264-P270-P280-P301+P310-P302+P352+P312-P305+P351+P338
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xn,T,Xi
Risk Statements
22 · 22-20/21/22-36-25-24-20
Safety Statements
23 · 23-26-36-36/37-45
RIDADR
2810 · 2810
WGK Germany
2 · 2
RTECS
875000 · DL0875000
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29342080 · 29342080
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2
Hazardous Substances Data
95 · 95-16-9(Hazardous Substances Data)
Toxicity
50 i.v · LD50 i.v. in mice: 95±3 mg/kg (Domino)
REACH Registrations
Active
Limited Quantities
5 L · 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)

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 items

Acute Tox. 3 (88.2%)

Acute toxicity (Oral) - Category 4

Hazardous to the aquatic environment (Acute) - Category 3

Hazardous Reactivities and Incompatibilities · 2 items

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/

Safety & protection

Disposal Methods · 1 item

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 items

1.1 [mg/m3]

13 [mg/m3]

75 [mg/m3]

Toxicology

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

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 item

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 items

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 item

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 item

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 item

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 item

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).

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
DL0875000
ridadr
2810
hs_code
29342080
Toxicity
LD50 i.v. in mice: 95±3 mg/kg (Domino)
risk_code
22-20/21/22-36-25-24-20
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
Xn,T,Xi
safety_code
23-26-36-36/37-45
hazard_class
6.1
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
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
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2
Precautionary statements
P264-P270-P280-P301+P310-P302+P352+P312-P305+P351+P338
Hazardous Substances Data
95-16-9(Hazardous Substances Data)

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.

Applications · 5 items

DescriptionBenzothiazole 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.

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

UsesIt 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 DescriptionBenzothiazole, 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 methods · 1 item

PreparationBy 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.

Upstream & downstream products

Upstream raw materials

Zinc sulfideN-Methylaniline2-MercaptobenzothiazoleAmmonium nitrateMolybdenum disulfideN,N-Dimethylaniline2-(METHYLSULFONYL)BENZOTHIAZOLE, 97Sodium methanesulfinate

Downstream products

Pramipexole6-AminobenzothiazoleDirect Fast Yellow RRDIRECT YELLOW 27Basic Yellow 242-(Phenylthio)anilineBENZOTHIAZOLE-2-CARBOXYLIC ACIDbenzothiazoline2-IODOBENZOTHIAZOLE2-(2-Hydroxyphenyl)benzothiazole2-Amino-6-nitrobenzothiazole2-Methylmercaptobenzothiazole

Additional notes

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