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2-(Methylthio)benzothiazole

PubChem CID
11989
Structure
2-(Methylthio)benzothiazole_small.png
2-(Methylthio)benzothiazole_3D_Structure.png
Molecular Formula
Synonyms
  • 2-(Methylthio)benzothiazole
  • 615-22-5
  • 2-Methylmercaptobenzothiazole
  • 2-(Methylthio)benzo[d]thiazole
  • 2-METHYLTHIOBENZOTHIAZOLE
Molecular Weight
181.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04
Description
2-methylthio-1,3-benzothiazole is an organic sulfide that is the methyl thioether of 1,3-benzothiazole-2-thiol. It has a role as an aryl hydrocarbon receptor agonist and a xenobiotic metabolite. It is a member of benzothiazoles and a methyl sulfide. It derives from a hydride of a benzothiazole.
2-(Methylthio)benzothiazole has been reported in Cichorium endivia and Apis cerana with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-(Methylthio)benzothiazole.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-methylsulfanyl-1,3-benzothiazole
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H7NS2/c1-10-8-9-6-4-2-3-5-7(6)11-8/h2-5H,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

UTBVIMLZIRIFFR-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CSC1=NC2=CC=CC=C2S1
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H7NS2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

31621-01-9
64036-43-7

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 NSC Number

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

2-(methylthio)benzothiazole

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
181.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
181.00199157 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
181.00199157 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
66.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
140
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Yellow liquid with an unpleasant odor; [Acros Organics MSDS]

3.2.2 Vapor Pressure

0.00026 [mmHg]

3.2.3 Collision Cross Section

131.32 Ų [M+H]+
S79 | UACCSCEC | Collision Cross Section (CCS) Library from UAntwerp | DOI:10.5281/zenodo.4704648

3.2.4 Kovats Retention Index

Standard non-polar
1589 , 272.73 , 273.74
Semi-standard non-polar
1607.1
Standard polar
2422 , 2422 , 2422 , 2422

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Nitrogen Compounds -> Thiazoles
Thiazoles
S79 | UACCSCEC | Collision Cross Section (CCS) Library from UAntwerp | DOI:10.5281/zenodo.4704648

3.4.1 Pesticides

Pesticides -> Fungicides
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
168653
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
J. Bourdais, Centre D'Orsay, Universite' Paris-Sud, Orsay, France
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
AMX-360
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.1.3 15N NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 7
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
JEOL JMS-01-SG-2
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

181 99.99

148 61.40

136 16.30

182 15.60

149 11.40

Thumbnail
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License
CC BY-NC-SA
2 of 7
View All
NIST Number
231790
Library
Main library
Total Peaks
119
m/z Top Peak
181
m/z 2nd Highest
148
m/z 3rd Highest
108
Thumbnail
Thumbnail

4.2.2 MS-MS

NIST Number
1001087
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
182.0093
Total Peaks
7
m/z Top Peak
167
m/z 2nd Highest
182
m/z 3rd Highest
183
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4.2.3 LC-MS

1 of 58
View All
Authors
Belova L, Covaci A, University of Antwerp, Belgium; Caballero-Casero N, University of Cordoba, Spain.
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
5 eV
Fragmentation Mode
CID
Column Name
ZORBAX Extend-C18 3.5um, 2.1x50mm, Agilent Technologies
Retention Time
5.564 min
Precursor m/z
182.0093
Precursor Adduct
[M+H]+
Top 5 Peaks

182.0093 999

166.9854 93

123.0135 3

109.0105 3

Thumbnail
Thumbnail
License
CC BY
2 of 58
View All
Authors
Belova L, Covaci A, University of Antwerp, Belgium; Caballero-Casero N, University of Cordoba, Spain.
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
ZORBAX Extend-C18 3.5um, 2.1x50mm, Agilent Technologies
Retention Time
5.564 min
Precursor m/z
182.0093
Precursor Adduct
[M+H]+
Top 5 Peaks

182.0092 999

166.9858 295

109.0105 15

68.9795 8

135.0147 6

Thumbnail
Thumbnail
License
CC BY

4.2.4 Other MS

Authors
KOGA M, UNIV. OF OCCUPATIONAL AND ENVIRONMENTAL HEALTH
Instrument
JEOL JMS-01-SG-2
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 75 eV
Top 5 Peaks

181 999

148 614

136 163

182 156

149 114

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
CAPILLARY CELL: MELT
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
168653
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.3.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

Catalog Number
168653
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Agrochemical Information

8.1 Agrochemical Category

Pesticides -> Fungicides
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

8.2 Agrochemical Transformations

2-(Methylsulfanyl)-1,3-benzothiazole has known environmental transformation products that include 2-Mercaptobenzothiazole.
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

9 Pharmacology and Biochemistry

9.1 Transformations

10 Use and Manufacturing

10.1 Uses

10.1.1 Use Classification

Pesticides -> Fungicides
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
INDUSTRIAL

10.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzothiazole, 2-(methylthio)-: ACTIVE

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Note
Pictograms displayed are for 93.2% (41 of 44) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 6.8% (3 of 44) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (93.2%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (93.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (90.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 44 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 3 of 44 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 4 notifications provided by 41 of 44 reports by companies with hazard statement code(s).

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.

11.1.2 Hazard Classes and Categories

Skin Irrit. 2 (93.2%)

Eye Irrit. 2A (93.2%)

STOT SE 3 (90.9%)

11.1.3 Hazards Summary

Reacts with water producing toxic fumes; May cause irritation; [Acros Organics MSDS] See Mercaptobenzothiazole.

12 Toxicity

12.1 Toxicological Information

12.1.2 Acute Effects

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Nature Journal References

13.7 Chemical Co-Occurrences in Literature

13.8 Chemical-Gene Co-Occurrences in Literature

13.9 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 UN GHS Classification

17.5 NORMAN Suspect List Exchange Classification

17.6 EPA DSSTox Classification

17.7 EPA TSCA and CDR Classification

17.8 LOTUS Tree

17.9 EPA Substance Registry Services Tree

17.10 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  4. EPA Chemicals under the TSCA
    Benzothiazole, 2-(methylthio)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  7. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. ChEBI
  9. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    2-(Methylthio)benzothiazole
    https://www.wikidata.org/wiki/Q15999703
  10. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  11. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
    2-(Methylthio)benzothiazole
    https://foodb.ca/compounds/FDB011171
  12. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
    2-(Methylthio)benzothiazole
    https://haz-map.com/Agents/19416
  13. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    2-(Methylthio)benzothiazole
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  17. MassBank Europe
  18. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  19. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    2-(Methylmercapto)benzothiazole
    http://www.nist.gov/srd/nist1a.cfm
  20. SpectraBase
    BENZOTHIAZOLE, 2-(METHYLTHIO)-
    https://spectrabase.com/spectrum/J5gIiADUYeH
    BENZOTHIAZOLE, 2-(METHYLTHIO)-
    https://spectrabase.com/spectrum/6YzS96zz9un
    BENZOTHIAZOLE, 2-/METHYLTHIO/-,
    https://spectrabase.com/spectrum/4Oh8blaQ2ja
  21. Metabolomics Workbench
  22. Nature Chemical Biology
  23. NMRShiftDB
  24. USGS Columbia Environmental Research Center
  25. Springer Nature
  26. SpringerMaterials
  27. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  28. Wikidata
    2-(methylthio)benzothiazole
    https://www.wikidata.org/wiki/Q15999703
  29. Wiley
  30. PubChem
  31. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  32. GHS Classification (UNECE)
  33. EPA Substance Registry Services
  34. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  35. PATENTSCOPE (WIPO)
CONTENTS