2(3H)-Benzothiazolethione (CHEM003813)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-09-11 05:19:30 UTC
Update Date2026-04-16 22:57:51 UTC
Accession NumberCHEM003813
Identification
Common Name2(3H)-Benzothiazolethione
ClassSmall Molecule
Description2(3H)-Benzothiazolethione is found in fruits. 2(3H)-Benzothiazolethione is a constituent of cranberries. 2(3H)-Benzothiazolethione belongs to the family of Benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-member ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2A
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3-Benzothiazol-2-yl hydrosulfideChEBI
2-BenzothiazolethiolChEBI
2-MBTChEBI
2-MercaptobenzothiazoleChEBI
2-Sulfanyl-1,3-benzothiazoleChEBI
Benzothiazole-2-thiolChEBI
BenzothiazolethiolChEBI
Benzothiazolyl mercaptanChEBI
CaptaxChEBI
MBTChEBI
MercaptobenzothiazoleChEBI
1,3-Benzothiazol-2-yl hydrosulphideGenerator
2-Sulphanyl-1,3-benzothiazoleGenerator
1,3-Benzothiazole-2-thiolHMDB
155-04-4 (Zinc salt)HMDB
2(3H)-Benzothiazolethione, potassium saltHMDB
2-BenzothiazolethioneHMDB
2-BenzothiazolinethioneHMDB
2-Benzothiazolyl mercaptanHMDB
2-Mercapto-benzothiazoleHMDB
2-Mercaptobenzothiazole (2-MBT)HMDB
2-Mercaptobenzothiazole (in liquid mixtures)HMDB
2-MercaptobenzthiazoleHMDB
2-MercptobenzothiazoleHMDB
2-MerkaptobenzotiazolHMDB
2-MerkaptobenzthiazolHMDB
2-ThiobenzothiazoleHMDB
4162-43-0 (Copper(+2) salt)HMDB
7778-70-3 (Potassium salt)HMDB
Accel mHMDB
Accelerator mHMDB
Accelerator mercaptoHMDB
Benzothiazole-2-thioneHMDB
Captax, bismuth(+3) saltHMDB
Captax, cobalt(+2) saltHMDB
Captax, copper(+2) saltHMDB
Captax, lead(+2) saltHMDB
Captax, mercury (+2) saltHMDB
Captax, potassium saltHMDB
Captax, silver(+1) saltHMDB
Captax, sodium saltHMDB
Captax, zinc saltHMDB
DermacidHMDB
DrmacidHMDB
Ekagom gHMDB
KaptaksHMDB
KaptaxHMDB
MBT, CaptaxHMDB
MebetizolHMDB
MebetizoleHMDB
MebithizolHMDB
Mercapto-benzothiazoleHMDB
MercaptobenzothiazolHMDB
MercaptobenzthiazoleHMDB
MertaxHMDB
Nocceler mHMDB
Nuodeb 84HMDB
Nuodex 84HMDB
Pennac MBTHMDB
Pennac MBT powderHMDB
Perkacit MBTHMDB
Pneumax MBTHMDB
RokonHMDB
RotaxHMDB
Royal MBTHMDB
Soxinol mHMDB
SulfadeneHMDB
Thiot axHMDB
ThiotaxHMDB
Vulkacit mHMDB
Vulkacit m, vulkacit merkapto/cHMDB
Vulkacit mercaptoHMDB
Vulkacit mercapto/cHMDB
Chemical FormulaC7H5NS2
Average Molecular Mass167.251 g/mol
Monoisotopic Mass166.986 g/mol
CAS Registry Number149-30-4
IUPAC Name2,3-dihydro-1,3-benzothiazole-2-thione
Traditional Name2(3H)-benzothiazolethione
SMILESS=C1NC2=C(S1)C=CC=C2
InChI IdentifierInChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChI KeyYXIWHUQXZSMYRE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazoles
Sub ClassNot Available
Direct ParentBenzothiazoles
Alternative Parents
Substituents
  • 1,3-benzothiazole
  • Benzenoid
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point177 - 179 °C
Boiling PointNot Available
Solubility0.12 mg/mL at 24 °C
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.26ALOGPS
logP2.88ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.9ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability16.89 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-4d37a61d9cd8301a62d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-d4138dd53c1e889f7472Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-5ee2ab0aad359223be6bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-902e833dd3cfb0b485b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0159-1900000000-fdf61c661e3992d0da85Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-05o0-3900000000-21acddd80ea821c4bf14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a59-8900000000-6da3258b33992f29c78cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9100000000-5be3cc8a800a6a145d24Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9000000000-dbb81dad2d0342550c70Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9000000000-2e115fed4acdabfa3234Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-671d8a90e7541628f6efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-2dfe8d8f0467dabe84e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-e8e5e62a5f0c06e02305Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-3ea865dce717e700b675Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-12367cc6bfe2d78f6b89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-9fafd8a0ed7180655284Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kr-1900000000-70d04c4c5fa82c738125Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-2900000000-58ddee392d1b19076ce0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05n0-9800000000-f9f390220b974d6fe5ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066r-9300000000-8b24e85baac451e5db6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0900000000-144cc4642f635cb7caa1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-104eed79a3d681c97064Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-8918e200add4938f2b7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-f0796ea4a78109f4545aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-672bbede5a3d7a91535cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-f00b14e4ed021b9e3ca2Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-6900000000-10352654a25e614d7e3dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11496
HMDB IDHMDB0030524
FooDB IDFDB002396
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID608157
ChEBI ID34292
PubChem Compound ID21831736
Kegg Compound IDC14437
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18568896
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18844695
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19158128
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21616561
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23063874
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23178179
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23340394
8. El-Bassi L, Iwasaki H, Oku H, Shinzato N, Matsui T: Biotransformation of benzothiazole derivatives by the Pseudomonas putida strain HKT554. Chemosphere. 2010 Sep;81(1):109-13. doi: 10.1016/j.chemosphere.2010.07.024. Epub 2010 Aug 6.
9. Teuber K, Schiller J, Fuchs B, Karas M, Jaskolla TW: Significant sensitivity improvements by matrix optimization: a MALDI-TOF mass spectrometric study of lipids from hen egg yolk. Chem Phys Lipids. 2010 Jun;163(6):552-60. doi: 10.1016/j.chemphyslip.2010.04.005. Epub 2010 Apr 24.
10. Tietge JE, Degitz SJ, Haselman JT, Butterworth BC, Korte JJ, Kosian PA, Lindberg-Livingston AJ, Burgess EM, Blackshear PE, Hornung MW: Inhibition of the thyroid hormone pathway in Xenopus laevis by 2-mercaptobenzothiazole. Aquat Toxicol. 2013 Jan 15;126:128-36. doi: 10.1016/j.aquatox.2012.10.013. Epub 2012 Oct 29.
11. Wang F, Cai S, Wang Z, Xi C: Synthesis of 2-mercaptobenzothiazoles via DBU-promoted tandem reaction of o-haloanilines and carbon disulfide. Org Lett. 2011 Jun 17;13(12):3202-5. doi: 10.1021/ol2011105. Epub 2011 May 17.
12. Tomc C, Kwasniak L, Shoureshi P, Nedorost S: Allergic contact dermatitis probably caused by mercaptobenzothiazole in thermal undergarments. Contact Dermatitis. 2012 May;66(5):294-5. doi: 10.1111/j.1600-0536.2012.02009.x.
13. Mitra R, Das S, Shinde SV, Sinha S, Somasundaram K, Samuelson AG: Anticancer activity of hydrogen-bond-stabilized half-sandwich Ru(II) complexes with heterocycles. Chemistry. 2012 Sep 24;18(39):12278-91. doi: 10.1002/chem.201200938. Epub 2012 Aug 17.
14. Amani A, Nematollahi D: Electrochemical synthesis based on the oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of nucleophiles. J Org Chem. 2012 Dec 21;77(24):11302-6. doi: 10.1021/jo302418p. Epub 2012 Dec 13.
15. Parham H, Zargar B, Shiralipour R: Fast and efficient removal of mercury from water samples using magnetic iron oxide nanoparticles modified with 2-mercaptobenzothiazole. J Hazard Mater. 2012 Feb 29;205-206:94-100. doi: 10.1016/j.jhazmat.2011.12.026. Epub 2011 Dec 17.
16. LITVINCHUK MD: [EFFECT OF 2-MERCAPTOBENZOTHIAZOLE (CAPTAX) ON THE BIL-SECRETORY ACTIVITY OF THE LIVER]. Farmakol Toksikol. 1964 Jul-Aug;27:493-5.
17. Roy DK, Bose SK, Geetharani K, Varma Chakrahari KK, Mobin SM, Ghosh S: Synthesis and structural characterization of new divanada- and diniobaboranes containing chalcogen atoms. Chemistry. 2012 Aug 6;18(32):9983-91. doi: 10.1002/chem.201200189. Epub 2012 Jul 10.
18. Joseph R, Kumar KG: Electrochemical sensing of acyclovir at a gold electrode modified with 2-mercaptobenzothiazole-[5,10,15,20-tetrakis-(3-methoxy-4-hydroxyphenyl)porphyrin ato]copper(II). Anal Sci. 2011;27(1):67-72.
19. Ahuja V, Wanner R, Platzek T, Stahlmann R: Appraisal of the sensitising potential of orally and dermally administered mercaptobenzothiazole by a biphasic protocol of the local lymph node assay. Arch Toxicol. 2009 Oct;83(10):933-9. doi: 10.1007/s00204-009-0426-y. Epub 2009 Apr 19.
20. Al-Ansari MM, Steevensz A, Taylor KE, Bewtra JK, Biswas N: Soybean peroxidase-catalyzed removal of an aromatic thiol, 2-mercaptobenzothiazole, from water. Water Environ Res. 2010 Nov;82(11):2285-9.
21. Fu XC, Chen X, Guo Z, Xie CG, Kong LT, Liu JH, Huang XJ: Stripping voltammetric detection of mercury(II) based on a surface ion imprinting strategy in electropolymerized microporous poly(2-mercaptobenzothiazole) films modified glassy carbon electrode. Anal Chim Acta. 2011 Jan 24;685(1):21-8. doi: 10.1016/j.aca.2010.11.020. Epub 2010 Nov 21.
22. Chen KJ, Lu CJ: A vapor sensor array using multiple localized surface plasmon resonance bands in a single UV-vis spectrum. Talanta. 2010 Jun 15;81(4-5):1670-5. doi: 10.1016/j.talanta.2010.03.023. Epub 2010 Mar 19.
23. Kuchta T, Bujdakova H, Sidoova E: Inhibition of yeast-mycelium transformation by 2-alkylthio-6-amino- and 2-alkylthio-6-formamidobenzothiazoles and their in vitro antifungal activity. Folia Microbiol (Praha). 1989;34(6):504-10.
24. Li N, Fang G, Liu B, Zhang J, Zhao L, Wang S: A novel hydrophobic task specific ionic liquid for the extraction of Cd(II) from water and food samples as applied to AAS determination. Anal Sci. 2010;26(4):455-9.
25. Ziegler V, Suss E: [The allergenic effect of rubber accelerators tetramethyl thiuram disulfide (TMTD) and mercaptobenzothiazole (MBT)]. Allerg Immunol (Leipz). 1974-1975;20-21(3):281-5.
26. Li XH, Tang ZX, Zhang XZ: Molecular structure, IR spectra of 2-mercaptobenzothiazole and 2-mercaptobenzoxazole by density functional theory and ab initio Hartree-Fock calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Sep 15;74(1):168-73. doi: 10.1016/j.saa.2009.05.026. Epub 2009 Jun 6.
27. Rajasekharan-Nair R, Moore D, Chalmers K, Wallace D, Diamond LM, Darby L, Armstrong DR, Reglinski J, Spicer MD: S-alkylation of soft scorpionates. Chemistry. 2013 Feb 11;19(7):2487-95. doi: 10.1002/chem.201202314. Epub 2013 Jan 7.
28. Perez-Quintanilla D, Del Hierro I, Fajardo M, Sierra I: Preparation of 2-mercaptobenzothiazole-derivatized mesoporous silica and removal of Hg(ii) from aqueous solution. J Environ Monit. 2006 Jan;8(1):214-22. Epub 2005 Nov 9.
29. Astigarraga E, Barreda-Gomez G, Lombardero L, Fresnedo O, Castano F, Giralt MT, Ochoa B, Rodriguez-Puertas R, Fernandez JA: Profiling and imaging of lipids on brain and liver tissue by matrix-assisted laser desorption/ ionization mass spectrometry using 2-mercaptobenzothiazole as a matrix. Anal Chem. 2008 Dec 1;80(23):9105-14. doi: 10.1021/ac801662n.
30. Kuchta T, Strakova H, Sidoova E: [Inhibition of Candida albicans transformation from the yeast form to the mycelial form by 2-alkylthio-6-amino- and 2-alkylthio-6-formamido- benzothiazoles]. Cesk Farm. 1989 Apr;38(3):139-40.
31. Borisova D, Mohwald H, Shchukin DG: Influence of embedded nanocontainers on the efficiency of active anticorrosive coatings for aluminum alloys part II: influence of nanocontainer position. ACS Appl Mater Interfaces. 2013 Jan;5(1):80-7. doi: 10.1021/am302141y. Epub 2012 Dec 27.
32. Metsios A, Verginadis I, Simos Y, Batistatou A, Peschos D, Ragos V, Vezyraki P, Evangelou A, Karkabounas S: Cytotoxic and anticancer effects of the triorganotin compound [(C(6)H(5))(3)Sn(cmbzt)]: an in vitro, ex vivo and in vivo study. Eur J Pharm Sci. 2012 Sep 29;47(2):490-6. doi: 10.1016/j.ejps.2012.07.011. Epub 2012 Jul 24.
33. Chipinda I, Zhang XD, Simoyi RH, Siegel PD: Mercaptobenzothiazole allergenicity-role of the thiol group. Cutan Ocul Toxicol. 2008;27(2):103-16. doi: 10.1080/15569520701713008.
34. Azam MA, Suresh B: Biological activities of 2-mercaptobenzothiazole derivatives: a review. Sci Pharm. 2012 Oct-Dec;80(4):789-823. doi: 10.3797/scipharm.1204-27. Epub 2012 Jun 18.
35. Song C, Wang Z, Yang J, Zhang R, Cui Y: Preparation of 2-mercaptobenzothiazole-labeled immuno-Au aggregates for SERS-based immunoassay. Colloids Surf B Biointerfaces. 2010 Nov 1;81(1):285-8. doi: 10.1016/j.colsurfb.2010.07.023. Epub 2010 Jul 15.
36. Pourreza N, Ghanemi K: Solid phase extraction of cadmium on 2-mercaptobenzothiazole loaded on sulfur powder in the medium of ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate and cold vapor generation-atomic absorption spectrometric determination. J Hazard Mater. 2010 Jun 15;178(1-3):566-71. doi: 10.1016/j.jhazmat.2010.01.122. Epub 2010 Feb 1.
37. Agnusdei CP, Mastronardi C: A case of severe psoriasis with an apparent incomplete response to anti-tumour necrosis factor alpha treatment. Am J Clin Dermatol. 2010;11 Suppl 1:41-3. doi: 10.2165/1153422-S0-000000000-00000.
38. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.